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Is Freelancing Right For You?

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I spend a lot of timing writing and podcasting about how to freelance successfully. I coach freelancers, have happily had my own micro agency for 10 years, and yes I do see freelancing as an amazing path to freedom. Freelancing has been right for me.

But is freelancing right for YOU?

Like anything in life from the big questions like religion all the way to your choice of breakfast cereal, there is no one size fits all. Freelancing can enable an amazing lifestyle for some, but be abysmally unsuitable to others.


What will freelancing look like for you? From my own experiences, and from speaking to hundreds of freelancers, it really depends on what type of person you are, and ultimately, what you want.

What Do You Actually Want Out of Life?

This is the critical question that a lot of people seem to overlook entirely. When selecting the work you want to do, it’s not sufficient to look at abstract metrics like “lots of money”, “being your own boss”, “lack of commute”, or “following your passion”.

Those are nice things, but they don’t answer the hard questions.

What do you want out of life? What gives you meaning? What do you want your day-to-day life look like (not vacation, but your typical average day)? What kind of work do you see yourself doing? What do you NOT want to be doing?

That takes some thought and internal reflection.

Derek Sivers gave an amazing talk at World Domination Summit 2015 on how different people optimize their life for different results. Some people may optimize for wealth, others for legacy, or fame, or freedom, or so on.

That struck me as very true. Furthermore I don’t believe that it’s really a conscious choice, so much as what you are built for deep down.

Personally I’m very much in the optimizing for freedom camp. This becomes very obvious when you look at my business history. Most of my successful outcomes have resulted from being true to this nature. And my biggest failures have come from trying to maximize something else at the expense of freedom, such as money or growing a big business for the sake of being big.

Freelancing seems particularly well-suited to those people that optimize for freedom. A well-run freelancing business can create freedom to choose your projects, freedom to choose your location, freedom to choose when you work, and yes, even financial freedom (a concept different than “having the biggest pile of money”).

Freelancing can also be a great fit if your optimizations benefit strongly from freedom. For example people that optimize for “adventure” or “family” would benefit strongly from the freedom that freelancing creates.

But there are other optimizations that aren’t a great fit for freelancing. For example serious wealth or fame rarely comes from one-on-one client work (yes, there are exceptions). If that’s your optimization pour yourself a very fine glass of wine and read How to Get Rich by Felix Dennis instead of continuing this article.

How Much Autonomy Are You Comfortable With?

There is a concept in psychology known as “locus of control”. People either have an internal locus of control, meaning they believe their own actions tend to determine the events in their life, or they have an external locus of control, meaning they tend to see the external environment as being responsible for what happens.

Freelancing is a form of business ownership. That necessarily means that you are now in the driver’s seat of your own little enterprise, instead of collecting a weekly pay cheque to do the work that someone else dictates. Suddenly you are the one that needs to make decisions, take ownership of the consequences, and be bloody persistent in getting what you want.

If you believe that your actions control your results, freelancing creates the autonomy and power to shape the life that you want to live, and to carve out success for yourself (however you choose to define “success”).

But if you tend to attribute your wins and losses to external forces like luck, market conditions, or the actions of other people (be honest), business ownership is going to be a tough road because it’s going to constantly feel like the universe is constantly saying “no” or that things aren’t turning out the way that they are “supposed to”. #realtalk

Are You Willing to Work For Others?

There are some profound differences between employment and freelancing. As a freelancer you are a business owner. You are also hopefully an advisor to your clients, rather than a simple order taker.

But while you are a business owner and advisor, you are also spending your days applying a skill that you know to directly create a result for someone else. This means you have to be willing to sell your services in exchange for money, and to spend a good portion of your working time delivering on this work.

For some people this is an amazing gig. You are get to spend your days honing your craft, your work creates amazing results for others, and you are getting paid for it all. If this sounds like you, freelancing is an extremely fortunate position to be in.

On the other hand, some people just can't deal with the idea of working for others. If having clients sends cold chills down your spine, freelancing is not going to be a good long-term fit. Some people are just not wired that way.

Are You Willing to Learn How to Market Yourself?

Learning how to promote yourself is one of the most valuable skills that anyone can learn, whether you're an employee, freelancer, product creator, or do any type of work whatsoever.

This skill allows you to get in front of, and be noticed by, the people who can benefit the most from your work. And it is a skill, to be learned like any other.

But in the world of employment, you can kind of get away without it. Yes it will affect the jobs that you get hired for, the salary that you make, and the promotions that you receive. But you can continue blissfully unaware and still have a pretty good job and a pretty good pay cheque.

On the other hand, learning how to promote yourself is mandatory as a freelancer. The gap between those that make the effort to learn how to promote themselves, and the ones that don't, is staggering. One group feels stuck trying to earn even $20/hr on job boards, while others see effective hourly rates in the hundreds per hour. I see it in my inbox and podcast interviews every week.

If you are somehow convinced that self-promotion is bs, or that you simply can’t/won’t learn it, then do not pass go. Do not start freelancing. You will not collect $200.

Does freelancing still sound like a great fit for you? Get started with my free two week email course.

Learn how to promote your services and find your first free clients with this free two week email course.

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