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Rules I followed for a decade of self-employed freelancing

by Lyndon Froese

Note: This is nothing polished. Just the ideas straight-up. I'd love your feedback:

I don't imagine my parents were exactly filled with joy and high hopes when I quit web design college, one year out of high school. I got a job at a call centre. Two weeks later, a miracle came to pass: I was hired at a web design company. I had applied to a few places before quitting school, but had given up on that, hence the call centre.

Less than three years later, I doubt many older and wiser in my life imagined I was setting myself up for success when I quit the Miracle Job too.

You see, I had read a book called the Four Hour Workweek and decided I'd had enough of the job thing. I remember telling my dad that I hoped to achieve this four-hour workweek. Seemed like a good idea to me, so at age 22, I was either unemployed or self-employed, depending on whether ye olde glass was half full or half empty.

It's hard to believe that it worked. I set up a very efficient freelancing operation.

This tiny book is everything I know about successful freelancing. There's a lot I don't know and that I'm wrong about, but here's what I've got.

Many hands dealt, many strategies to play

I'm not including any techniques that I have not personally used.

Everyone has a unique deck of cards. Your deck might not be much like mine. And there are many ways to play a hand. Never-the-less, we have many more card game cliches to get to, so let's get on with the rest of the book.

Prerequisite: A skill to pay the bills

This book is for people who already have a kind of skill that has proven value on the market. That means that you or other people are already selling the same service.

If you don't already have a skill like that, there are lots of freelance-able skills you can learn by taking online courses or reading 20 books. Either way, in the words of my cousin Moe, you gotta have the skills to pay the bills.

More and more jobs are being to be done by independent contractors, since being in an office is less important, thanks to our friend the Internet.

To give you some ideas, here are some things that are currently possible to do as a freelancer:

Pick two of three

Skills matters, but they are only one part of this complete breakfast.

There are many freelancers who have been more skilled than me in the actual craft, yet they haven't had much work come their way.

Here are three attributes of a great service provider:

You only need two.


Likeable + Skilled. "Well, she's always late, which can put me in a bind, but I like the her and the work is good"

Likeable + Reliable. "Well, the work is so-so, but I can always rely on him and he's a nice guy"

Skilled + Reliable. "Well, the guy is a jerk, but I can count on him to hit deadlines and it is always good work." In real life, I work with an illustrator sometimes who doesn't give the warm fuzzies. That's okay – I'd be hard-pressed to find higher quality work elsewhere.

If you are extremely skill or extremely likeable you might be able to get away with 1/3:

Very, very skilled."She's always late and I'd never want to have a beer with her, but gee, the work is incredible. I would put up with almost anything for that quality." (Artists at the top of their game may be able to get away with this. For example, Hunter S Thompson was famously horrible to work with.)

Very, very likable."Well, he's not very reliable and the work is mediocre, but he's such a nice guy – I almost feel like he's a son to me and I want him to succeed. We always have such a great time together too" (This kind of likeability may be difficult to teach)

People mostly do business with people they like and trust, and that's what this book is mostly about.

Attitude is everything

When I played high school basketball, our warm up shirts had the phrase "Attitude is Everything" printed on the back. I didn't like that very much since I wanted us to be more like a professional team with professional warm up shirts. But, a quick anedote about the power of having a positive attitude when talking to clients:

I'd never had a client leave me for another business, so I let things slide a bit on the Reliability dimension. Then a client left me for a larger company where his cousin worked. This was my own fault since it would have been easy to provide more reliable service. I was surprised when a couple months later, my old client called me and said that he missed working with me. He said he wasn't "feeling the love" at the new company. All they would have had to do is be more cheerful on the phone.

Getting going

Open for business

Begin by telling people what you are doing. Tell anyone who asks you what you do or what your plans are for the summer. You are freelancing, as a writer, a piano player, IT support person, writer, PR person or online marketing consultant – whatever it is your are doing, say it. If you need work, you can't be shy about saying you are open for business.

I have no idea how I had the courage to do this at first. When people asked what I was doing I said I was going to freelance as a web designer. I had no customers and no plan for how I would get them. I remember being asked how I was going to get customers and having no idea. What did I even say to that? Didn't matter.

My first customer came from a referral from a family friend. He passed on my name to one of his connections. Had I not had the courage to tell this family friend that I was going to be freelancing, I never would have got that first customer.

That first client meant I was really in business. And it was one of the greatest thrills of my life.

Over ten years later, I still serve that same client.

Don't play business, do business

As a freelancer you may never have to register your business with a government agency. You may never need an accountant. In Canada, if you don't expect to pull in more than $30k in revenue in your first year, you don't even need to charge GST. If you want, you can just start.

If you don't want to operate under your own name for some marketing reason, you can operate under any name, without permission from anyone. The Higher Power will have nothing to say if you make a website called Canadian Gopher Consulting and start consulting gophers on a wide variety of gopher issues. Just get the cheques written out to your actual name – dust off your birth certificate to double check the spelling.

Until you actually do some billable work, no one is sending you cheques anyway, so you can cross that bridge later. If you can't make any sales for your services, registering a business name would be a waste.

Do business. Don't play business. (Got that one from Noah Kagan, who has lots of material on the topic)

Many people don't start their projects because they need to get unimportant ducks in a row. Do you really need business cards or are you just playing business instead of doing business? Get cards once you are annoyed with yourself a few times for not having them yet. You may never need them.

You don't need a perfect website before you start your business. Maybe you can just throw up a Facebook Page for now so you can get to work.

You don't need social media accounts.

You don't need a bookkeeping program before there are any books to keep.

Optimize later.

Business plans

I never made a business plan. I thought business plans were dumb. But I was also 22 and kind of dumb myself.

You probably don't need to make a formal business plan, but it might not be a bad idea to jot down some of the ways you plan to acquire customers. Beyond that, as a freelancer, if you are spending time writing a business plan, you may be playing business when you could be on the phone rustling up work.

Any plan is better than no plan

Even a bad plan is better than no plan. Maybe your plan is to get work by holding a sign whilst wearing a chicken costume on the boulevard. This is better than no plan. If it doesn't work, it's back to the drawing board for Daurice.

Where first clients come from

Once you start doing excellent work for people and they're telling their friends, getting work becomes easier, but even from the start it is possible that all your work will come from word of mouth. Thankfully, mine did.

Your existing networks will all know that you are now a freelancer (because you followed the Open for Business rule) and we know that you have a skill that other people regularly pay for. If you aren't getting work this way, you may need to grow your network, or get know more people who are more likely to know people who need your services.

Growing your network

If you don't have enough friends or connections to get work, you can try:

It's like fishing. You need to be putting the lines in the water.

Do that too

When I first started freelancing, I decided I was going to be a web designer. I would make websites. My former boss, Dan, convinced me that it was better to be the everything provider. Yes, I can do your website. I can also make a poster for you. I can make your letterhead. Yes, I can edit those photos. So many Yes We Cans, it would make a long-time Republican a believer. Yes, I can make a campaign video for you even though I don't know how… yet.

People won't necessarily distinguish between things related to your area of competence and things actually in the wheelhouse of the SS You. Be "their guy" they can call, or their gal. "Oh we need something related to marketing or computers? Get the guy!" Or gal! He or she, doesn't matter, cuz they gonna take care o' business!

Anything that's outside of your skillset, outsource it. There are lots of service providers, but not everyone has work. And the most skilled ones aren't necessarily the ones with the work. So if you have the work, hire others to help you. Your clients will know that they can call you for whatever and you'll get the job done – no need to go anywhere else. There's also a huge load-balancing advantage to doing this, to reduce the feast and famine dynamic of freelancing. More on that later.

You'll also end up expanding your skillset this way.

If you want, you can specialize later when you have a ton of work. Or, instead of specializing in a task, you can "specialize" in a customer or two (ie. have very few clients).

The other path: By being a specialist you can become incredible at one thing and become known as the person to go to for that thing. I once hired a fellow to help me with digital audio signal processing. I was looking for someone who knew how to do this using a specific math approach. Soon after finding him, I was in conversation with someone who could talk with me about an esoteric topic like it was as obvious as the weather. He knew of this math and had done lots of this kind of work. He charged me lots of money. If you choose this path then your plan will be to relentlessly get better at your speciality and perhaps write about it on the internet until you have lots of work coming in. Deepen your skills every day until people are coming to you.

But your specialty can also be that you are a generalist that your customers can use year after year for a wide range of things. New relationships are risky for both parties, maybe you can just keep working for the same few clients. That's what I have done.


Trust is economic grease

Do everything you can to gain and retain your clients' trust.

A lot of this writing is about trust.

Trust is the most durable negotiation tool. Having your client's trust means you spend more time working and less time negotiating.

People will pay much more to work with someone they trust. People will rarely take a risk to find someone better if they trust you.

If you are trusted, you'll have more say over the direction of the project, which (if you're good) means the work turns out better.

Returning customers are the best customers

Focus more on retaining customers than on getting more. For one, this means you'll naturally provide better service to your clients because you're focused on them. There are also compounding advantages for both sides every day a relationship goes on. The longer they know you, the more they'll trust you and the more you'll understand their needs and, therefore, the harder it will be to replace you.

It is also very time consuming to be replying to RFPs that you probably won't get picked for, unless you have a serious number of credibility indicators (ex. done work for well-known clients or having a portfolio you can show that everyone perceives as outstanding). It will take you hours to put together your proposal, which is a shot in the dark.

It's much better to be sought out individually, where they found you and want to work with you if a deal can be struck. But even then, it is still much more effort to get to the point that you're getting down to work, compared to working for existing clients.

New relationships are risky. You don't know if they will pay the bill or if they'll have very different ideas than you on how things should work. And your new client doesn't know what to expect from you. Understably, they'll want you to describe every little detail before you do the work, which can sometimes take more time than the actual work.

Once trust has been established, details don't need to be discussed as specifically. You may not need to give exact quotes since your customer has worked with you before and your bill has always been fine.

By the second, third and fourth project, you already know what they like so you don't have to be guessing nearly as often.

You already know that they'll pay their bill so you necessarily have to worry about being collecting 50% up-front, if you don't want to bother with that.

You can just get to work.

Do what you say you'll do, especially early on

When beginning a relationship with a possible new client, build trust early by simply following through. This is low hanging fruit, Sanka.

They know nothing about you, so they'll be looking for anything that will suggest whether you will be a good partner for them, or a bad one. If you have an initial phone meeting scheduled for 3:00PM, call them between 3:00PM and 3:02PM (not a second earlier). If you say you'll have a ballpark estimate to them by the next day, have it to them by the next day – or earlier.

If you are capable, sustain this through the entire relationship and get major points in the Reliable dimension. One of the Golden Rules of getting along with your fellow social apes is to do what you say you'll do.

Whenever I have failed at this it has been at my own peril.

Focus on similarities with your client

If they like sports, but you don't really care about sports, there must be something about it you can still talk about an appreciate. Seriously, like even if it's that you like the colour purple, you can say that those purple jerseys they have are nice. If they say they are from west of the city, and you are too, say that and talk about it. People love to connect on these kinds of things. Find similarities. People trust people who are like them.

Say things like "People like us..." or "I'm like you, I..."

Don't pretend to know things you don't

When I worked at the web design company, many years ago, there was one programmer there that on a number of occasions told me that something was possible that was not actually possible, and he told me things were impossible that were actually possible. This is very inefficient. In the moment, it was convenient for him to seem like he knew what he was talking about, but in the end it is bad for everyone.

The minute a subcontractor commits this sin, is the minute I start thinking I'd like to replace them with someone who has "I don't know" in their vocabulary.

It's okay to say that you'll have to look into it. You can say that you know someone who is an expert in that area and you'll get their two cents. There's no rush. And if there is a rush, explain that you aren't sure, but you can tell them where you'd put your money, given the rush situation.


Look good, smell good

Someone did some research on good looks of political candidates and how we voted. We voted for the better looking ones. But, when we were asked whether we would ever be swayed by looks of these candidates, we said no. We don't know we do this, but everyone does.

This isn't fair, but we're animals, so we have to work with it.

Fortunately, some of "looking good" is in our control. Take some care in selecting an outfit. Yes, people can tell if it is in the bottom of your laundry hamper.

Never have bad breath at meetings. People will judge you for it. They will hate talking to you no matter how smart your words are. Same thing with nose hairs. Same thing with ear hairs. Same thing with dandruff. I sometimes present as a bit of a bush man at this point, not only because I literally live in the bush, so I've failed at all these things, but it's always been at my own peril.

Skill and character are all the matter in Lyndon's Utopia, but in the more interesting real world, people have very deep reactions to these things. We can't help it. You will be perceived as smarter, funnier and more trustworthy if your look and smell are pleasing to people. You will get better treatment from everyone, everywhere you go.

Dress the part

What we wear gives valuable signals to others about what's going on in our brains. Smart business people dress one way, capable mechanics dress another way. If you want good treatment at the auto parts store, wear coveralls.

People also like dealing with people who are somewhat like them, so if you are going to meet a client at a high rise downtown you may want to be in a dress shirt, but if you are meeting a client out on their farm, some clean plaid and a pair of jeans in good shape will be the meal ticket.

I have often not followed this. For example, I show up in meetings with a ridiculous mustache that had my client referring to me as Dirk Diggler because he thought I looked like a 70s porn actor. Another time I went to a business meeting in bare feet because of some experiment I was doing. My client and I were kicked out of the restaurant. Real professional.

Life is easier when you conform a bit and take advantage our shared cultural symbols.

Or, take the opposite tack. There's a very rich, very famous investor in California named Chris Sacca who is well-known for doing all business in cowboy shirts. That sounds like a lot more fun. And so Dirk Diggler lives to see another meeting.

Never arrive early

If you go to a meeting early to provide great service, you accidentally broadcast incompetence instead. Although your intention is good, by coming in early you put pressure on them to finish whatever they were doing before. People don't like this. They wonder why you don't understand this. They'll wonder why you failed to imagine that they might be busy.

Instead, go for a walk around the block and time it exactly. Arriving one minute late is a good target.

Never arrive late

Some basketball player (can't remember who!) once recommended that to change your life, be 45 minutes early for everything. There's a vast difference in how it feels to travel to a meeting if you are early, compared to borderline. Forty-five minutes seems crazy, but if you are chronically late for everything, extreme circumstances require extreme measures.

I followed that 45 minute plan for a while. And it was nice to be 30 minutes early. I had time to make phone calls, respond to emails or read a book. I could go for a brief walk and think about what I'm going to say in the meeting. Best of all, I was not late.

It's a bad sign if you begin every meeting with an apology.

Especially if you are not used to being on time, you'll probably really enjoy feeling like a pro.

Have a Hit-By-A-Bus plan

Since I provide on-going, recurring services to clients, I have on occasion been asked what happens if I suddenly die, or just randomly disappear to Mexico.

I have a deal with a fellow freelancer who knows how to do everything I do. She will take over my affairs. I agreed to do the same thing for her. This information is now outdated, so it can be shared safely, but for a while there was a secret note hidden between the pages of Calvin & Hobbes' The Days Are Just Packed on my bookshelf. My colleague knew this and that it would contain all she needed to gain access to everything she would need. There was little about the note that would make sense to anyone else.

It is responsible to have a plan like this if your customer would be in a bind without you. But, since bus deaths are rare, its main utility will be to be impressive to your prospective clients. Holy – you really take things seriously and thought of everything.

Take notes during phone calls

When you have a phone meeting, take notes. Afterwards, make sure you have a good summary of what was discussed. It doesn't have to be much, but at least enough to jog your memory. With email discussion, you can check back to see what was said, but with phone calls, you may not remember what was discussed. Projects often drag on so long that there's no way you could recall exactly.

If there is a disagreement, you can always say that you looked at your notes and they said such and such. If you can't remember what you estimated for price or suggested, you'll be glad you have those notes so that your proposal doesn't suddenly go from $1000 to $1300 for no reason that you can explain. What, are you just pulling numbers out of the Tickle Trunk or what?

Take notes during meetings, 'topless of course

Always write down what people say in meetings. Do it into a notebook rather than into a computer. Laptops are no good because people can never tell what you are doing typing into that thing.

A laptop also creates a physical barrier between you and them, which has a psychological effect.

Besides allowing you to actually remember what was discussed, people feel honoured to have their words written down. They also never have to worry that they'll have to repeat themselves. When I'm speaking and the other person isn't taking notes, I expect them to forget things, and they usually do.

Use the phrase "You've come to the right place"

When I was a kid, I took guitar lessons. On the get-to-know-ya initial lesson, the teacher asked me what I was looking to learn. I told him and he said "You've come to the right place".

This phrase exudes confidence. Obviously whoever said it is confident enough in their skill to take care of business here. It's in their wheelhouse.

The phrase also affirms that you did something right. "Oh me? I came to the right place? Well, at least I finally did something right!"

It's also a welcoming thing to say. It says you belong here.

It also shows that you've been listened to. They took the time to listen to what you were looking for. Then, they could have replied by saying that you weren't a good fit, but instead. They thought about it and said "You've come to the right place". Who can say no? I can't!

Say that phrase and then deliver.

Use the phrase "Tell me about your business"

This is one I got from my boss Dan. It's magic for a few reasons.

  1. People will feel honoured to tell you about their business. People love talking about themselves and oftentimes their work is their identity..

  2. Asking them to start at the beginning also means you aren't jumping to any conclusions about what they need. Even if they have come to you with a specific request, getting the lay of the land might mean that you could help them tweak the concept. Sometimes people will start telling you what they need before you have any idea of how it fits in. In that case, you should listen to them, since you should always listen, but as soon as you can, get them to talk more broadly about their business and what they are trying to do.

  3. The more information you can get, the easier things will be when it's time to negotiate a price. For example, if the specs they are asking for end up being too expensive, if you know a lot about their business, you may be able to offer a cheaper alternative that would fit. Or, you can make a better value-based argument for why the project will be worth it. (More on this later).

"Tell me about your business", is a great way to turn the conversation towards the matter at hand in a meeting. You can small talk. You should small talk! But then it's time to get to work, say "So tell me about your business".

You want your client to do lots of talking.

Customer service

Be a Dougasaurus

One time I decided to try to contact the guy who wrote the By Mennen jingle. I found him on the Internet and emailed him. Turned out his name was Doug Katsaros, or Dougasaurus, which he said he tried unsuccessfully to get other people to call him. A little while later, we were talking on the phone. It turned out he had not only written the By Mennen jingle, but he had played piano and written parts on two dozen gold records or platinum records by Michael Bolton, Rod Stewart, BB King and Peter, Paul and Mary. He had been hired to impersonate Elton John for an Elton John record where Elton didn't feel like recording his part over again. Dougasaurus had played on albums by KISS, he wrote vocal parts for superstars to sing on Frank Sinatra's duets album. He played on Bon Jovi's first album and claimed that when he listened back to it, he thought some of the high notes were actually sung by him.

I asked Doug why so many artists wanted to work with him. He said that one thing lead to another. He did one and the customer was happy and then he was recommended for the next job.

But why, I said. There must be many keyboard players.

He said, for one thing, he's a happy guy. People like to have happy folks in the studio.

"I'm also not too precious about what I play," he said.

Most service providers get all upset when someone says that they don't like their work, and can you do it another way for this very annoying reason? But Dougasaurus just said "Oh okay, how about this instead?"

This may seem like a recipe for mediocrity, that your work is going to be degraded by taking instructions from those who don't know what they're talking about. That may be true if your real work is graphic design, piano playing, writing or whatever is printed on your business card, but I made a choice early into my freelancing. I chose to make my work to please customers. I have ended up with piles of time outside of "work" to do projects that I pour my heart and soul into. For me, freelancing is about doing what's best for business.

I almost never push back when one of my clients asks for a change in something I've made for them. Almost every time I have tried to convince a client of something, they are A) Unconvinced, and B) I have wasted creative energy trying to come up with a great solution to a problem they weren't interested in solving anyway, C) My client was not made to feel smart, and D) We don't feel like we are on the same team as much anymore. Now I just say "No problem!" and make it work.

I will gently make suggestions. That's my professional duty. But once I've gently suggested it, I'm happy to just do whatever the client wants. Half the time they are right anyway.

Or, you can do the opposite: Stive to be an artist, not a technician. Stick to your guns. Only do work you are proud of. Push for what you think is best. Only work with people who can be convinced. Have your own style, your own thing you do. Be hired for that style and vision.

Your esteemed clients

"Sailing would be easy if it weren't for the wind" – Seth Godin

Back when I had an actual job, some of us employees were talking negatively about a client. Such a dumb customer, I'm sure of it! Our boss, Dan, said "Oh you mean our esteemed client?"

Your clients are your business. If they always understood everything, they wouldn't need you.

Sailing would be easy if it weren't for the wind. Your job is handling the wind. The more wind, the better, since you'll know that others won't be able to hack it. Make difficult customers your specialty.

I have had several clients that I'd heard others say they could not work with. Those customers love me. I'm proud of this.

We'll go into how to do this in other sections. It's like a superpower, but for now never complain about your customers. Be thankful you have them.

Without the wind, you aren't going anywhere.

Always be positive

Always be happy to talk to your customers. Always tell them your are happy to be doing the work. Always tell them that you enjoy working with them. Tell them you are happy to be part of the team. If you aren't, there's something else wrong.

You don't have to be Tony Robbins here. You won't always feel like talking to your customers. What's important is that you make an effort to be positive. Smile while you talk on the phone. Your customers can hear it.

Jump-to-Conclusions matts

If you client is saying the sky is falling and everything is going wrong and implying that it is your fault, do not defend yourself. Do not tell them how to fix it – not yet. Definitely don't tell them that it's not a problem and they should simmer. The first step, always, is to make sure they believe that you have heard them.

Client: "The thing isn't working! You said it would work but it doesn't work!"

You could begin defending yourself, but instead…

You: "Uh oh, that does not sound good. It's very important that it works. Can you tell me more about what's going on?"

You are now on the same team as them.

Always address emotion first and the best way to change the emotional game is to get on their team. Be very slow to assume a them vs. you posture. Even if they are on the attack, respond as if you are tone deaf to this, because you are on the same team.

Say "Let's figure it out"

Once your client has said what they need to say and you understand what's going on for them, it's time to get into solving the problem. A good transition is to say "Okay, let's figure this out". This begins the conversation about solutions, and it also says to them that you're on their team. It moves them into a cooperative state, if they aren't there already. It also says that you are confident that there's going to be a solution, which there is.

You can make sure your client knows that you are committed to figuring it out – you can do that without taking on any fault that isn't yours to bare or agreeing to any specifics. It'll mean a lot to your clients and orient the conversation in the most productive way.

Say "What else?"

This is another Cousin Moe Special from my cousin Moe.

If your customer came to you with an issue (whether they thought it was your fault or not) and you have an agreement about a solution to their problem. Say they can consider it done. Then say "What else?" We aren't doing the bare minimum here. Continue asking "What else?" until they say that will be all.

A complaining customer means you up to bat. A home run is to make that customer into a zealot because you understood what they were feeling and by the end of the call they felt differently. A strike out is when they feel like you didn't understand and you only cared about yourself.

Very few people can hit home runs because their egos get in the way. If you think of yourself as up to bat, you now have a new way to have a proud ego. If you can turn this situation around, you can feel like a boss since you know the interaction could have gone so much worse.

The customer is always right (in their own minds)

When people complain, you want to find a way to respond that they are right. Grant Cardone, a famous sales person says the words "You're right" is music to people's ears. You need to get yourself on their team. If they perceive that you are on their team, you have a chance at coming up with a solution that will work for both of you. If this is a debate or a war, it won't end well for anyone.

The best mindset is to first try to hear what is true about what they are saying. Or imagine how they are coming to the conclusion that they are. Then respond accordingly. If you need help, just say "You're right…" and then complete the sentence. They may not be right about everything, but they are definitely right about what they are feeling.

Or, let's say they aren't mad, but just asking for a revision that you mostly disagree with. Find something to agree with them on. If you agree with them on the problem, but not on their solution, agree with them on the problem and then ask if they might be open to another way of solving that problem. You can say that their solution could work (I mean, it is always possible that it could), but ask them if, for the sake of brainstorming, it would be better another way?

If your client says it should be blue, but you think it should be orange because their competition is already using blue, you can say "Blue would look great." Then you can say that you made it orange because you thought it would be good to be different from the competition. Then add something about blue being a trustworthy colour and you get that too. Then say "It's up to you!" and assure them that you are happy either way.

If a customer says the beer you made tasted bad. You could say "Well it won last year's award for the best breakfast beer". Or you could say "Very true! Lots of people say that. My mother-in-law didn't like it either. What kind of beer do you normally drink?" They say Bud Light. You say "Gotcha. A nice light, crisp taste that isn't too filling. You might like our Crystal Clear beer. It tastes basically exactly like water with a bit of a bready taste." Of course, as we will discuss in the pricing section, you are charging enough for the beer that you can actually give the customer a free Crystal Clear every now and again.

No one leaves unhappy

Make it your company policy to never have a client leave unhappy. This is great for customer retention, but also for your reputation.

This is another policy I got from my former boss.

Use their words

Many servers will take your order and say "Good choice". That's fine, but servers who simply repeat back to you what your order is in exactly the same words get 20% more in tips.

When you are being hired as an expert, your client is going to use inaccurate words for things. Sometimes you should gently explain terminology to them, if it helps clarify the conversation. But, if you can, use their words. If they call it a computer program, don't call it an application. If they call it a website, don't call it an application. If they call it the "backend", don't correct them and say that it is actually the frontend of the admin area they are talking about since the term "backend" is reserved for server functions and databases.

Using as much of their vocabulary as much as you can makes you easier to understand. It reduces unnecessary complexity in the conversation. They'll feel more like you are similar people since you share common language. It helps them feel smart, which they probably are.

If you know what they mean, you know what they mean.

Using fancy words can make you seem like a god

Expertly teaching your clients new vocabulary can makes you seem like you know your shit. That's a good thing. But you must do this without making them feel stupid. (More on that in the next section).

Another good place for industry jargon is on invoice descriptions because it makes it seem like you have unusual knowledge that they don't have, which is true. For example, instead of saying that you "Added Contact form" onto the website, which makes it sound like you might have just clicked a few things to insert it into some magically website word processor thing, say "Laid out and coded Contact form, including JavaScript validation, database storage of submissions and automated email send".

This may help your client because they can show their boss this invoice and it's clear they hired a real expert and it was a good call to outsource the work.

Speak to your clients like they are a smart person

Make sure your clients feel like no question is stupid. Make it seem like it is the most normal thing in the world that they don't know the answer, or better yet, make them feel smart for not knowing – why would they have wasted time learning about your esoteric field when they can just hire you. That's why they are hiring you and they are smart for hiring you. Like that time when you didn't know how to re-do the wiring in your house and you hired a pro. Share an anecdote like that.

I have listened to people talk to others and I could swear they are pretending to not understand what the other person is say. It's like they are upset that the wrong words are being used. Try to understand your client instead of teaching them a lesson for being stupid. Which they probably aren't.

Thank your clients and invite them back

Whenever you send an invoice, it's a nice touch to say how glad you were to work with them and that they should let you know if they ever need anything else.

Become a student of psychology

The more you understand people, the more power you have, the more you'll be able to give people what they want and have them give you what you want. And the world will be a lot less confusing.

The book Thinking Fast & Slow helps explain a lot.

People often aren't talking about what they're talking about

I had a client upset that I didn't answer the phone. She sent me an email to express her anger. It turned out that she thought I didn't want to talk to her. She imagined that I saw her name on the screen and ignored it. Understandably, her feelings were hurt. I said that I understood. I explained that I actually had not seen that she'd called because I was working on a different project. I explained that I try not to look at my phone while I'm working for someone because I want to give the task at hand my full attention. This removes the connection of my actions from the deep pain we all remember from the playground as a kid.

If you don't want to give a client exactly what they are asking for with their words, maybe you can figure out what they really crave and give them that in another way that works for you.

Always try to understand real motivations and desires. Never expect others to know what their own motivations or desires are, much less be honest about them with you. I recommend making it your job to figure it out.

Avoid talking about bad news over email

If you need to discuss something that might be perceived as negative (for example, asking for more money on a project), do it on the phone. This shows that you care and it gives you the chance to have dialogue. You'll be able to read their response. You need to know they are happy with the situation and that they feel respected. You do not want them stewing over it.

Time to get brave and pick up the phone.

Communicate through your client's preferred channel

It's pretty easy to figure out how people prefer to communicate. Those who love meeting in person will immediately want to get together for coffee. I they suggest beers, that's a dead giveaway they love socializing. If they like talking on the phone, you'll know it because they'll respond to your email by the phone. If they prefer email, they'll do the opposite.

Mirroring their behaviour will make them feel like you are similar to them, which they will like. Plus they will love you for being happy to communicate how they want, rather than like those other people who do it wrong. Your clients will praise you for this.

Have the mindset that all mediums are great for their own reasons. This way your customer will always be right when they say "I love working with you because we can actually talk on the phone. Some of these others guys just email and they are doing it wrong". As discussed, the customer is always right, so you say "Oh man, you can really get a lot done on the phone and it's also good for understanding another person fully because you can get the inflections in their voice". The customer is also right if they have the opposite opinion for equally valid reasons.

You may have your preferences and they can be taken into account, such as the fact that I don't really do in-bound phone calls. But if someone calls me on the phone and leaves a message, I make a point of calling them back, rather than trying to get the conversation over to email right away, which is my preference.

However, if the customer calls me and leaves a message and I call back and get no answer, then I will definitely send them an email saying I got their message. I will ask them what they were calling about and how I can help.

There's a give and take here, and it's fine to not give anything, but if you are avoiding the phone because it is scary, it's time to get used to phone calls... by making phone calls. Or if you hate writing, now is the time to learn to write.

Be aware when you bring negative value

Much of my business today is not really freelance, but providing on-going tech services to businesses. My customers pay me on a monthly basis for things to just work. When things do not work, I have delivered negative value to them. This isn't a "thanks for nothing" situation. This is a "thanks for making my business worse" situation. Therefore, for me offer them their money back, or a free month of service, communicates that I do not understand their situation. In cases like this, I'll have to find another way to regain the trust of my client and restore our relationship.

Never say "Sorry for the inconvenience"

When you screw up, never say "Sorry for the inconvenience". Your client may not feel that the word "inconvenience" really sums up the issue. It's a cliche that is said when people are really not sorry, or do not think the issue was a big deal.

How to apologize

Don't be shy about apologizing. You don't have to take full responsibility for something that isn't all your responsibility, but you can always apologize for your part in it. If your client is disappointed with something, well, you can always do better at managing a client's expectations, so it's okay to shoulder some of the blame, and then explain your perspective – in that order.

An excellent apology has three parts:

  1. Acknowledging what the fault was, as precisely as you can.

  2. Expressing your regrets.

  3. Saying how you'll avoid the situation in the future.

Just taking responsibility can reduce damage to a relationship considerably or almost entirely. Not apologizing when it is your fault is at the very least annoying.

Who is to blame?

If you don't think you owe your client an apology but you suspect they may think you do, make sure to talk it through with your client. It is very important that both of you see the situation the same way, that you share a common narrative of what happened.

Manage expectations

As a project manager (which you are as a freelancer), it is your job to discover what your client is expecting and to make sure that that matches your own expectations. This might mean laying out specs carefully. This also might mean anticipating things that your client may assume are part of the specs, but are not. The better you get at this, the smoother your projects will go. Do not put this on the shoulders of your client. That's what shady businesses do with their fine print.

The actual craft

Skill development is a bargain

Very few people get much better at their skill after their career begins. This is because it is difficult to learn new things and most people will only do it if they are more or less forced. The few who continue to learn even after they have work are at a serious advantage.

Career capital

The more demand there is for your services, the more you can call the shots. This is sometimes called "Career Capital". Accept that you may have to compromise if you have little career capital. You may have to take on work that isn't your favourite. If you are a writer, the progression might be something like this:

  1. Writing for free for your university paper.

  2. Writing for a newspaper, covering things you find dull.

  3. Writing more interesting stories for that same newspaper, but still having to bang it out fast.

  4. Writing for a magazine that want longer form stuff, but the stories you do are still dictated by your editor.

  5. Being an editor-at-large that can write anything they want.

  6. Being so well-known that you can ask almost any publication if they want a piece and they'll be overjoyed to pay you (Malcolm Gladwell status)

Take time to learn fundamentals

You'll save yourself a lot of time and headaches down the road if you take some time every now and again to learn the fundamentals, the depths, of your craft. This will also be very impressive to your customers if they ever get curious and start quizzing you.




I'll always remember when I was in my early 20s, my friend Mike said that his mentor told him this story: "There are two violin makers, right across the street from each other. One charges $1000 for a violin, the other charges $100. Some people want the $1000 violin, some people want the $100 violin".

Charge properly upfront instead of nickel-and-dime-ing your customers later

Take these two scenarios:

Scenario 1: You tell your client the work will cost $500. The specs seem clear enough at first, but it turns out that the specs aren't quite what the client needs, even though they signed off on them. The client, or you, didn't think of something in advance that they clearly need. You should have thought of it, or anticipated that your client might think it is included. You can charge them a bit more to add the needed feature. Now it costs $550, even though they were expecting $500. No one likes this.

Scenario 2: You tell your client the work will cost $800. Specs turn out to be a bit wrong, but you just say "Sure, I can make that change". Everyone likes this.

Your customer would rather pay $800 than $550.

It is NOT the dollar amount that matters. It is perceived respect that matters. It is perceived honesty that matters.

No one likes the car garage that tacks on a bunch of stuff to the bill that make sense to the mechanic, but were not anticipated by the customer.

Charge more than you need to up-front so you never need to nickel-and-dime.

There will always be unexpected things in projects. That's your job to know this. Charge enough to allow for some waves and hiccups.

Charge enough to be taken seriously

When I first decided to freelance, I decided to charge an amount that I could hardly imagine saying to someone. It was 2.5x the hourly wage I had been making doing the exact same work at the firm I worked for. I could hardly imagine saying this to prospective clients, but I had read stuff saying that you shouldn't undercharge and you need to remember that you'll have to pay for your own root canals.

My former boss asked what I was planning to charge. I told him and he told me that I should charge at least 25% more to be taken seriously.

I gave myself my first raise before I even began.

Charge enough that you don't mind your time being wasted and you don't mind eating shit

If you ever find yourself feeling like your customers are wasting your time, one possibility is that you feel this way because you aren't charging enough. You never want to be bitter about your customer asking you to do things. This is bad for everyone involved.

You'll always be happy to do pointless things for clients if you charge a good rate for my time, no matter if the work has value or not. I always try to steer my clients away from things that seem pointless, but people think differently about things and sometimes I end up doing work that I don't see the value in. My clients are probably better business people than me anyway, so how can I be so sure it's pointless? Doesn't matter, anyway. I'm here to serve and I charge enough that I feel like its a good deal for me, and my clients wouldn't hire me if they didn't think it was a good deal for them as well.

Charge enough so that your customers don't waste your time

When you don't charge very much, your customers will ask you to do all kinds of stuff that they could easily do themselves. For example, if you are an accountant and you find a lot of people are dropping off shoe boxes, one possible solution is to raise your hourly rates to encourage folks to submit their information in an organized fashion. Same thing goes for meetings. If you are cheap, there's no harm in having you come down for meeting after meeting. But if meetings are expensive, your client will be more likely to be organized and ready to go when you arrive so you can get things done. And if not, hey, see the above rule.

Flat-rate vs hourly

I always give my clients the choice.

I prefer to do estimates based on hours. They are buying a chunk of my time. This means during the project, we can have discussions about whether it is worth using the budgeted time on another meeting or some feature that may not be mission-critical. But, I always tell clients that I can do a hard quote if they prefer. Having the option to go for a hard quote actually makes it easier to accept the hourly system, since they are not being forced into it. No one wants to be forced into some unknown cost situation. But I can tell them that it allows them to keep the specs more loose, which reduces their workload at the beginning of the project.

If they choose flat-rate, I try to be as clear as a possibly can with the specs – instead of saying they are buying some bunch of hours, they are buying a specific deliverable. Set the specs so they give you lots of ability to say that something is outside of the scope of the project. You can always have a generous interpretation of the specs, because you're charging enough not to nickel-and-dime, but you want to be able to refer your client to the spec sheet if the scope is creeping.

Spell out as clearly as you can what the project does not include, if you suspect your client might think it will include those things. You'll be happy you took responsibility to manage their expectations. And, of course, make sure to charge properly because the specs will never cover everything the customer needs or wants in the end.

Justifying your price

If you are charging a high hourly rate, focus on value. One time I told a client that my consulting rate was higher than the technician rate I had charged him before. He called me saying that I was robbing him or something. I said that I always try to bring more value than I charged for. I asked him if he thought that my services weren't worth the price. He said he was just giving me a hard time, which may or may not be true, but it didn't matter.

Now I do this preemptively. I recently raised my prices for new clients and I remember on the call I even debated just saying my old price since the new price felt high. I decided to say it, but then immediately said that I wanted her to always let me know if she felt she wasn't getting good value. She said that that sounded great. I say this all the time now. It makes me feel a lot better about charging my rates and the client feels respected and in control.

Negotiate in real time

It is better to talk price in real-time, over the phone or in person. If you are throwing around ballpark numbers, you will be able to suggest much higher prices in person. You can do what Boss Dan called the "Fall off the chair test" to see if they fall of their chair when you say a high number that it could, possibly, potentially cost, if you include the kitchen sink. If you send that high number over to them by email, they may write you off as expensive and go elsewhere, meanwhile there is actually lots of room to negotiate the price and change the specs to meet their needs at a lower price. In person, you won't scare them away because you always get a chance to talk about it.

Slow down negotiations, especially if you are a weaker negotiator

A stronger negotiator who wants to take advantage of a weaker one, should speed up negotiations and make a deal. This is part of the reason car salespeople are always pushing to make the sale. If they were bad negotiators, this would be as bad strategy for them too.

I sold a sweet Westfalia van for less than I could have last summer because I let a strong negotiator speed up the negotiation by saying that he was hoping to make a deal that very day because he was a long drive away. I was asking $10000. He said $7000 cash, today. I said I'd have to think about it, but I switched the topic to something else about the van to buy time. Then when they were more or less ready to hit the road because I had said I would have to think about it, I suddenly said $8000, today. He said that the most he could do was $7500. I told him I needed 20 minutes to think about it. I literally left him and his girlfriend there on the sidewalk as I walked away to think about it. This was good except since I was dealing with a superior negotiator and I wasn't desperate to sell, so I should have just told him I needed to sleep on. We settled at $7800.

Your clients will ask you for prices right there in the meeting. When you don't give them prices, they will ask for ballparks. This is understandable. But, it's often smart not to throw out any numbers until you have a really good feel for the project. For me that means thinking it through on my own, without them there.

There's a point where you have to throw out some kind of range for the sake of the conversation, but wait as long as you can. The longer you wait, the more information will come out, the more time you'll have to go over details in your head.

Almost always, my clients have been happy with me saying that I'll need to think through the details and I'll be able to get them a ballpark or estimate or quote within two days, or one day or whatever makes sense. There are always things I forget in the heat of the moment, and once you give a price, even a ballpark, your client will not like changes to it. This is all a part of your job to manage expectations.

Give them the opportunity to say a price first

You can often build a project around their budget. If you find out they are thinking somewhere around $1000 and not somewhere around $10000, you don't have to waste time putting together a $10000 quote that they won't accept anyway. And if they say there were thinking $10000, you can put together a stellar proposal with no corners cut.

What's your mobile phone number worth?

I asked my former boss how they could charge $30/month for web hosting when you could get it from GoDaddy for $10/month. He asked me how much one hosting-related phone call from your client is worth? Even if they only call once per year, that still might be half an hour of your time. And you have to be on call. How much is it worth to have your cell phone number?

You can use this to explain your prices to client. I have used this many times to explain my prices and sell the value. I literally say, "and you'll have my cell phone number, if anything goes wrong". For many, this is so much better than a dreaded call centre that the bigger competition will obviously make them call.

If it gets you two sales, it'll pay for itself

Because you are using the line "Tell me about your business," you'll be able to figure out how the project is supposed to make their processes more efficient or sell their products. You'll be able to go through the math with them about how many additional sales made or hours saved will mean the project has paid for itself. Say "Okay, so if the project costs $2000 and each sale is worth $100 to you, then if the project is going to make at least 20 sales, it pays for itself". If you really are bringing value, these calculations can make you a no-brainer.

I've also convinced clients not to hire me using this same math. This is another advantage to returning customers: you have value to them in what you dissuade them from doing and they'll know you'll be straight with them next time too.

Sanity and having the life you want

Know what your business is for

If your business is to give you more freedom over your time and more mobility, let this inform all your business decisions. Remember this every time you are tempted to do something that will maximize profits instead of lifestyle.

Always have a reserve fund

Save up for a rainy day fund and then never touch it. Keep it somewhere difficult to access, such in mutual fund where you have to sign something to get it out. You may have lean months and if you are worried that you might actually not be able to make rent, you will not enjoy freelancing.

Also: the hungry don't get fed. If you are never desperate, you will be able to be more choosy with projects and be a more effective negotiator. You can't do well in a negotiation if you have to make the deal. If you have to make the deal, the other party can ask for whatever they want.

Eat lobster, eat lentils

You'll be a much more powerful negotiator and happier freelancer if you know you can always go back to eating rice and lentils. If you know how to eat on a $1/day, you never have to worry about whether you can put food on the table. You can eat as much lobster as you want, but you need to know that you can do lentils if need be.

How to take vacations

Tell your clients in advance, ideally. But you can also rush away, if you have no active projects. You can have someone take care of your affairs. I've had these kinds of auto-responders:

"Hi there. I'm on vacation for two weeks, returning mid June. If you're emailing about something that can wait, then I look forward to being in touch when I return. If you need something right away, please don't hesitate to contact my colleague Melody who will help you out. She has access to all logins and client files and is in charge of things while I'm away"

How to not be tied to your phone 24/7

One thing that was important for me was not to be tied to my phone at all times. So I don't often answer my phone. This is less than ideal for some customers and it has meant that my business didn't grow as much as it would have otherwise. But I never wanted my business to grow more than to support me. And I have enough customers that I can have some say in how things are done.

I sometimes have had clients ask me why I don't pick up the phone very often. I explain that it's my policy to focus on the task at hand, whether that's paid work or otherwise. I tell them that when I work on their project, I don't take calls for other clients. As a computer programmer or writer, distractions and interruptions will introduce errors and bugs. As a friend, distractions during a conversation can introduce shallowness of relationship.

Plus, being on-call all the time was not an option for me since control over my time and location (including locations where cell reception is no good) was part of the point of my business. There would be other ways to avoid being a slave to your phone while still being on-call for your client though – for example, teaming up with someone else or hiring someone to take calls for you.

Load balance by outsourcing

If you can outsource some of your work, it may be a good idea to take on more work than you need at times, take on that extra customer that you don't need. This means that when things get lean, you just stop outsourcing stuff and do it all yourself. This reduces the feast or famine issue that a lot of freelancers run into where they can't keep up sometimes, but are worried about their next meal other times.

Trick yourself out of bed

Since my surroundings change so often (now I'm living on a boat, in two months maybe I'll be in the arctic), my routines are often changing. But this past winter, I had a solid number of months where I spent almost all of my time alone in a ski-in cabin in the woods. I developed the following morning routine, which involved tricking myself to do things:

  1. Woke up to an alarm clock.

  2. I was then lying in bed with no particular reason to get up. I was living in frozen Canada in wood-heated cabin. I was procuring my own firewood from the forest around, using a toboggan to haul the wood back to the cabin, so I often didn't stoke the stove much at night and thus by the morning, the cabin was near zero, which makes it even more tempting to stay in bed, especially since there was no particular reason to get up. Also, since I had complete freedom over my time, I was totally responsible for my choices for how I was going to spend my life, so there were many "existential" questions about that to think about as I pondered getting up. The solution is to plan something truly enjoyable as the first thing in the day. For me, that thing was listening to an audiobook or podcasts. The deal was that I could listen to any audiobook or podcast that I wanted to, no matter if it was useful or challenging. I could be anything. And I would do this as I would go for a ski. It feels good to walk or ski in the morning, and my favourite thing to do in all of life is to listen to audiobooks and podcasts.

  3. Once I was up I would already be feeling more energized and realize that I might as well make a fire so the cabin would be warm when I return.

  4. I would go for my ski and audiobook time. Since exercise is so important for my state of mind,

I introduced a rule to keep me skiing longer. I could listen to audiobooks as long as I skied, but before I went back inside the cabin, I had to take the earbuds out. And, I had something not that fun scheduled for the next thing, which I would try to avoid by – guess what – exercising more.

  1. Once back in the cabin, it was Shit Together Hour. This is time set aside to do all the things I've been putting off. This means answering emails, making phone calls, paying bills and any maintenance of life. I was no allowed to have coffee until Shit Together Hour was done.

  2. Coffee time. This was my reward.

  3. Now high on caffeine, I was ready to do any interesting creative work I wished to do and the rest of the day was unstructured.

The idea is that we can defeat bad habits and improve our lives by smartly designing structure. I try to avoid relying on will-power at all costs, since willpower doesn't really work very well.

A good book on this topic is by the guy who makes Dilbert. It's called How To Fail at Almost Everything and Still Win Big.

Good luck out there

That's all I have for now, but feel very free to get in touch with me for any reason. I'm always happy to chat:

I'll be making updates to this from time-to-time. Until then, good luck out there!

And thank you for very much for taking some time to read. Always an honour.