How do you know when you've "made it" as a freelancer?

Feb 3, 2015

When you and I were children, dear reader, “success” was a bit easier to quantify.

Your little drawings and essays got stickers and smiley faces. Then you got older, the assignments got longer, and you got letter or number grades. Were they always satisfying, or correct? Do those scores mean much to you now? No – but at least they were quantifiable.

Now, we’re ostensibly grown-ups – despite our predilection for candy binges and silly video games. And I don’t know about you, but sometimes I long for someone to grade my development in adulthood. Am I doing an ‘A’ job? Or a 'B’? How do I know?

When you’re a freelancer, it can be difficult to gauge when you’re “successful.” When you’re first starting out and scrambling for clients, success means not actively starving to death. But as you gain more and more experience, and work with more and more clients, that “success” benchmark rises. Pretty soon, “successful” can mean working only with clients who pay you the rates you desire. Then it means working only with clients who do the work you’re interested in, WHILE paying you your preferred rates. Your rates rise. Your quality of life bumps up a little. You start turning down work, getting pickier -- you weed the limpest projects out of your portfolio.

So when are you successful? When have you finally “made it?”

After several years of freelancing full-time in a variety of fields, I have made a slightly dismaying discovery… you kind of never “make it,” entirely.

Don’t get me wrong! You can set goals and meet them. You can get more confident and more secure. You can try new things, fall flat on your face a few times, and gain experience. You may even achieve things that seemed impossible when you first dreamed them up. It can be very satisfying, and it’s important to be grateful.

But in life – and particularly in freelancing, where you often set your own path, the goalposts for “success” keep shifting.

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You’ll never get to a place where you are completely, 100% satisfied with your work. There will always be some new challenge to overcome, some new skill to learn, some new achievement to rack up. And if you ever do feel absolutely, 100% satisfied… odds are that the feeling will be deeply impermanent, or that you will swiftly become profoundly bored.

The nice thing about the transient nature of this kind of “success” is, however, just that – its impermanence. It means that there is always room for growth, for development.

Conversely, if you’re feeling unsuccessful (and who doesn’t feel like a failure some percentage of the time?), you should keep in mind that that feeling, too, is temporary -- just because you are despairing now doesn’t mean that you will always despair. The struggle to meet (or surpass) our ever-changing goals doesn’t start with failure, and it doesn’t end with success – it’s a lifelong thing. If you never ever feel like you’re failing or disappointing expectations, you’re probably an unrepentant narcissist or aiming too low.

I’ve started to try to redefine my “success” as the process of meeting and setting goals – rather than achieving specific goals itself. By embracing the temporary nature of success itself, I can focus on personal growth instead of jumping from gain to unsatisfying gain. That means less dissatisfaction, and more curiosity; less pressure, and more exploration.

It can be tempting to wish for an A+ for life, but if those grades are (and were always) meaningless anyway, why not try to enjoy the learning experience?

Kate Hamill lives and works in New York City, where she consumes an inordinate amount of Sriracha daily. You can catch up with her on Twitter at @katerone.