Where does freelancing fit into your overall career?

When you’re 90 years old and you look back at your life, where is freelancing going to fit in to your career path?

In this episode, we discuss how freelance writing and self-employment fit into your overall work life. This episode is for people who have gone in and out of freelance work, aren’t sure it’s for them, or are midway through their career and can’t figure out how to start.

Fitting in freelancing

We hate the phrase “side-hustle”…but that’s the reality for a lot of freelance writers.

Having the security of a full-time position gives you the wiggle room to see how things go with freelancing so you can see if it can turn into a viable career option. We often advise people not to drop everything and jump in with both feet. But there’s no one-size-fits-all approach to freelancing. 

  • Some people have very demanding jobs that are overwhelming. And when you’re mentally and physically exhausted at the end of the day, it can be hard to motivate yourself to work on your freelancing career. If that sounds familiar, maybe jumping in with both feet maybe is the right answer for you.

  • If you have family, kids, or other responsibilities, that can be even more of a challenge. Having some financial runway saved up (6 months or so) can make you feel more comfortable when taking the plunge. 

It’s important to know yourself, and what you can handle at any given moment.

“If it’s something you want to do, you can carve out an extra hour or two every day to fit things in.”



We’ve noticed the further along you are in your career, the harder it gets to leave the cushy perks behind. If you’re working at a startup in the Bay Area, at Google or Facebook, for example...that’s a lot to give up.

That’s why we’d suggest trying freelancing sooner rather than later. The sooner you give it a shot, the less you have to lose.

Know yourself

It’s a theme we keep coming back to in these talks because it’s just so important: Figure out who you are, and then figure out how you can act on that.

If it means quitting your job, then so be it. If it means doing it as a side-hustle, sure. There’s no right or wrong answer here. Some people view freelancing as a stepping stone in their careers; they do some work freelance, and then they go in-house if that’s the right choice for them.

There’s no failing at freelancing. It’s about whatever works for you. We don’t think going and getting a full-time job after trying it alone is a failure. If you’re struggling, try working in-house for a few years, then go back to freelancing with a fresh perspective.

“I just felt so trapped in a 9-5 office job. I knew I could be more efficient, earn so much more...I knew that freelancing was the thing I’m supposed to be doing.”

Freelancing can fit into many stages of your life. If you’ve recently retired then you might find yourself with a lot of free time on your hands. While the financial aspect might not be so important, you could be interested in giving back to the writing community or leaving a legacy.

For other people, freelancing means flexibility. And if you’ve got kids at home, that might be something that’s really important to you. If you recently lost your job, or just got a bunch more free time, there’s plenty of freelancing gigs to fill that void.

“We’re all in different seasons of our lives. There’s pros and cons to each side, and not everything about being a freelancer is rainbows and sunshine.”

Working in-house (especially in the US) has its advantages. If you’ve got a family then you know that healthcare premiums can add up, and that’s something you’d have to pay out of pocket as a freelancer. Maternity leave is another pro to working for a company. A lot of companies in the Bay Area offer six months. Can you afford to do that as a freelancer?

The most important thing is to ask yourself where you are in life right now. 

We recommend bouncing ideas off a mentor or coach. It can be a real challenge to come up with these answers on your own, so have a serious think if freelancing is the right choice for you. As long as you’ve saved up a six-month safety net, don’t be afraid to experiment. Decide what makes the most sense for you, at whatever stage of your life you’re at. And don’t make a choice until you’ve come up with the hard answers.

Remember: your career is a jungle gym, not a ladder…so enjoy it.

Subscribe to the Freelance Writing Coach podcast and stay tuned for more tips.

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