Turning your side hustle into a full-time job

Seven strategies for going all-in on your passion

Published in

Steady

5 min readNov 25, 2020

Are you working all day and then recording podcasts all night? Shooting videos all weekend to the point that your friends complain they never see you, or getting up an hour early each day to write your newsletter, then arriving at work already exhausted?

Making the leap from employee to self-employment can be tricky, but thankfully the transition is usually temporary.

If that sounds like you, or if you’re still dreaming about how to make your media side hustle work full-time, here are some tried-and-true strategies to consider. Think of this as a pick-and-mix — find a couple of strategies that resonate and tailor them to suit your needs and goals.

1. Pick up your first freelance gig

It makes sense to test the waters before you dive in. So try offering your skills on a freelance basis to a couple of customers first, while maintaining your regular job. See how it feels and consider what it might feel like to work this way full-time.

As you spread the word about your work and word-of-mouth picks up, you might find yourself working nights and weekends, heading towards overload. This is a good problem to have, but it isn’t sustainable. It’s probably time to take the next step!

2. Set realistic goals

How much work would you need to have in order to safely step away from your full-time job? Would you need to be earning enough to cover your bills, 50% of your full-time earnings, or some other figure?

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Find a number that feels safe and make that your goal. It’s likely to be significantly less than what you earn full-time, but that will only be for the short-term. Once you’re able to let go of your full-time job, you’ll be freed up to explore the full potential of your freelance hustle.

Alternatively, you might be more of a time-oriented goal setter. In that case, focus on a plan for quitting your job. You might not feel ready right away, but that’s ok. There’s never going to be a perfect time to quit, so it can help to set a realistic goal for your transition date. That might be six months from now, on January 1, or by the next summer holidays. Then you have something to aim for, ensuring you won’t drag out the decision indefinitely.

Saving up

At the same time, it would be smart to start squirreling away some savings to make up the shortfall you can expect when you first jump into full-time self-employment. This is another way to keep yourself safe during those tricky first months.

3. Consider reducing your hours

Once you’ve set your target, it’s time to get to work hustling that self-employed income. You won’t feel safe to quit your job just yet, but it’s time to start thinking about it.

You might start by reducing your work hours to four days per week, giving yourself a little more time to build up your self-employed income.

4. Look out for the tipping point

As you grow your hustle, you might find your side hustle starting to become, well, more than just a side hustle. You need to keep an eye out for the tipping point — the moment when you suddenly have too many freelance articles to write to combine with your day job, for example. Your bank balance might be climbing quickly, but you find you’ve got no time left for your personal life.

There’s always going to be a gap to jump, but if you can bridge it, you’ll soon be on the other side, with more manageable working hours, doing the thing you love full-time.

5. Find a unicorn

There’s another way this transition could go down: finding one big gig that covers all your monthly bills, freeing you up to experiment with the rest of your work time.

Finding just one regular, well-paying freelance job that can offer you enough work to create a sense of stability can quickly turn your side-hustle into full-blown self-employment. So keep an eye out for big opportunities — just like a unicorn, you never know when one might show up and change your life!

6. Try memberships

If you host your own podcast, blog, newsletter, video channel or other media project, memberships offer a way for your community to support you directly by paying monthly contributions that give you a reliable income for your work.

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7. Quit on good terms

When it’s time to say goodbye to your full-time job, remember to exit amicably. Who knows? You might be able to offer your services to your former employer as a newly-minted independent contractor.

Depending on your relationship with your boss, you might even be able to give them a head’s up on the changes you are planning to make in advance. That way, they can be more supportive when you get busy picking up bits of extra work and help you make a plan for you reducing your work hours.

As you can see, going all-in on your side-hustle isn’t one-size-fits-all. Choose the path that feels most manageable for you, set your goal, and before you know it you’ll have made the leap to self-employment.