How to Make Freelance Your Amazing Career—Part 1

I just passed nine years as a freelancer, and I’ve been thinking about the ups and downs I’ve experienced along the way.

At the same time, I’ve been having a series of ongoing conversations with another freelancer who is struggling right now to understand how to grow his business to the next level, or if he even wants to.

I asked him point-blank yesterday if he really wanted to be a freelancer. Could he do this for another 20 or 30 years? Would he want to?

“Not really. I’m just tired of stressing and looking for work all the time.”

We dug into it a little more, talking about whether or not he should get a job instead, etc.

Ultimately though, he concluded that he would have a hard time making nearly as much at a job, and he’d miss the freedom and flexibility of being a freelancer too much to go back to working for someone else.

So he’s trapped.

I want to be clear: this is a really successful freelancer. For the last few years, his earnings have been around $200k annually.

So what should he do? Can he continue freelancing as a career and have it not drive him insane for the next 30 years?

How do you sustain freelance year in and year out for decades without losing your mind?

Great tactics like value-based pricing really make a big difference in the short-term, but building a career out of freelance means you need to pay attention to some long-term things as well. Because value-based pricing doesn’t help when you have no clients, or you’re in the wrong specialty for the times, or your marriage breaks up because you’ve been working too much.

Yes, value-based pricing is important to help you avoid those things, but these are some next-level strategies and mindsets that I think we all need to focus on to take our freelance to the level of “amazing career”.

So I’ve been thinking about what it takes to build a successful career as a freelancer, not for a few years, but for 30 years or more.

1. Move from freelancing to consulting

A lot has been written about how you shouldn’t call yourself a freelancer, and I agree with that. I rarely refer to myself as a freelancer outside of my writing to other freelancers. It just has bad connotations for a lot of people.

What you call yourself isn’t that important though. What matters more is how you present yourself and what you’re selling.

Freelancers are typically viewed as free-roaming technicians: someone with a set of skills selling their time on a short-term basis.

By contrast, a consultant is someone who is an expert not just in the technical skills in question, but in how to leverage them for business results.

One of the most critical skills you can master to go from freelancer to consultant is to put yourself in the shoes of your clients and realize that they’re trying to buy a business result, not your time, experience, or technical skills.

The more you can focus on selling them those business results (delivered by your technical skills), the better.

In the long run, this will not only earn you more money and respect, it will help protect you from becoming a commodity. There are lots of writers, designers, developers, etc. But there aren’t nearly as many who can translate those skills to the bottom line of the business in a way that makes hiring them an easy decision, even if they’re expensive.

2. Build business development systems

Do you know any freelancers who were once flying high, making tons of money, and then a couple years later are struggling to find work?

I sure do. I’ve been that freelancer. There have been periods when I relied too heavily on lucky breaks to make enough. Things worked out for awhile, but when there was a hiccup, I was suddenly scrambling to try and find work, and my skills were rusty.

To last decades in this business, you need to build and maintain systems to bring you new work consistently without relying on luck.

3. Make more than you need to

The hardest thing about freelancing over the long-term is the high degree of uncertainty. You will face slow periods, personal tragedies, economic calamities, and emotional struggles.

If you don’t want to be forced back into having a job when these times come, you need to build up margin and build your business in a smart way.

I wrote a whole guide about how to make your business downturn-proof.

However, what’s been interesting to me is that margin not only protects your downside, it also unlocks your upside.

Margin gives you the freedom to have time, money, and mental energy to take bigger bets and be more aggressive in trying to grow your bottom line, knowing that you have the margin to take some shots and miss while not suffering financially as a result.

For my part, I hit the mental point of knowing that I could freelance for the rest of my life once I was able to make 50% more than I needed to by working with 3-6 great clients per year, with the core of my work taking around 30 hours per week.

The relationship I had with clients at that point was a much more collaborative, trusting one, where the focus was on the value of the work we were doing together, not the number of hours I was billing.

Additionally, I had been able to execute a few strategic moves in my business up to that point, like switching from web development to being focused on mobile dev & consulting, which gave me confidence that I could adapt to a changing market over time.

And most importantly, I enjoyed the work and the lifestyle.

More specifically, I began to enjoy an unexpected part of freelancing: finding new work.

The reason was that finding new work now looked pretty different. I was looking only for projects worth tens of thousands, with great clients who valued my expertise, and I didn’t actually need those projects.

That made a call with a potential client feel less like a desperate grasp for survival, and instead an interesting conversation, which might turn into tens of thousands of dollars for doing interesting work. And if not, that was fine too.

It is one of life’s great unfairnesses that the best way to get a great client engagement is to not need it.

I’ll talk more about this in part 2, but if you’re only making enough to live on (or less), it’s sometimes easier to reduce how much you need to make to create margin than to try and make a lot more than you currently are. Once you create that margin, you can get your income up more easily.

4. Be part of a community of freelancers

Freelance is lonely.

A lot of freelancers work from home, and the bulk of their discussions about their business are with their significant other or friends. While that’s valuable too, people who aren’t freelancers often don’t really understand what goes along with it.

I have shared an office for the last five years with another freelancer, and while we drive each other crazy sometimes, it’s incredibly valuable to have someone who gets it. We run strategies past each other, ask for advice, and occasionally even vent about clients 🙂

So whether it’s a coworking space, sharing an office with another freelancer, an online group, or sharing a table at a coffee shop with a freelancer friend once a week, find a few people who do what you do who understand the joys and frustrations of this lifestyle.

5. Be balanced in your lifestyle and work

The freelancers I know who work the most almost invariably are earning poverty wages.

Ok, not quite poverty, but way less than they should be.

And looking at their lives, you can see it slowly destroying their health, their relationships, their mental state, etc.

Most of them won’t be freelancing in five years, let alone 30.

No matter what your career is, balance and taking care of yourself are important, but I think freelancers often are particularly bad about work/life balance. One of the great things about freelance is that it rewards hustle, but too many freelancers confuse “hustle” with “working 90 hours a week”.

So please, set boundaries, work reasonable hours, don’t answer your phone or email 24/7, go outside regularly, take care of your health, etc. You’ll be 100% happier and you’ll make more money in the long run too.

By the way, this is one of the many reasons that it’s insane to charge hourly. You end up working 70 hours to bill 40, and still make far less than you could have if you worked half the time. Please, don’t charge hourly!

6. Have a big goal you’re working towards

I think it’s really difficult to work on anything for decades without having some kind of goal in mind.

My goal with freelance is financial independence, which for me means having $3mm – $5mm in the bank. That’s the point at which I could stop working forever and have enough to live a very good life off the investment returns.

But I won’t stop working. I’ll just shift the nature of the work I’m doing a bit. And I’ll have even more margin to go out and chase bigger fish, whether as a consultant, investor, founder, or something else.

And truthfully, the destination isn’t as important to me as the journey is. You have to do a lot of things right over long periods of time to have $3mm – $5mm in the bank. You have to build a good income, be disciplined with your spending, save a lot of money, invest smartly, and ride out a lot of bumps. And you have to have the mental discipline to do those things for decades.

The transformation that results in achieving that goal is more important to me than the goal itself.

So whatever your goal is, have one, take it seriously, study people who have reached it, focus on it intently, and work towards it every day for as long as it takes.

7. Be open to new opportunities

This article is about how you can build a sustainable freelance career that can last decades, but I would also encourage you to be open to new opportunities.

I know more than one freelancer who had built amazing careers who ran into an unexpected opportunity to switch to selling products, build an agency, or start a startup of their own. They weren’t actively looking for those opportunities, but they were open to them when they came.

So even if you think you want to do this forever, be open to the possibilities that life puts in front of you.

8. Be honest about what you’re giving up

I had my last job when I was 24 years old, and while I don’t intend to ever have a job again, there are a few people, firms, and projects out there that I’d probably go work for under the right circumstances.

The reason is simple: it’s tough as a freelancer to be a core part of certain things that are bigger than yourself. I look at the work that’s being done at great companies, non-profits, and government organizations today and it does make me a little sad because I know that while I could contribute to those teams as a freelancer, it wouldn’t be the same.

Similarly, there’s a lot of opportunities for prestige and public recognition that we’re probably passing up as freelancers.

I’ve (mostly) come to terms with the tradeoffs that I’m making by choosing this lifestyle, but I think it’s important to be honest with myself about them.

These aren’t todo items

Finally, these aren’t things you need to figure out today. I’m still working on all of them myself. These aren’t really destinations or todo items. You can’t ever finish the things on the list above. They’re more like perspectives, ways of looking at the world. They’re tools to shape your thinking so that you’re more powerful and purposeful in your actions over time.

However, I like actionable advice, so next week in part 2 of this post, I’m going to give you some actionable steps that you can actually start doing today to make progress towards these goals. Make sure you sign up below to get it!

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