How to Go from Side Hustler to Full-Fledged Freelancer (28).png

When you’ve worked in a job for a number of years, you can get pretty comfortable.  Pretty much everything is taken care of for you – your paychecks come at a regularly scheduled time, someone in human resources selects your health insurance and other benefits for you, the sales department is always on the hunt for new clients, the computers are all set up and the computer folks are ready to help you out when something goes wrong.  All you have to do is show up for work on time and do your job to the best of your ability.  Sounds pretty sweet, doesn’t it?

In addition to your sweet gig, you’ve done a little work on the side, here and there.  Maybe you just needed to make some quick cash to pay an unexpected expense.  Maybe your 401K took a hit and you wanted to make a little extra money to add to your retirement fund.  Whatever the reason, over time, you found that you're actually enjoying your side hustle a lot more than the full-time job you’ve put your time and energy into.  You’re ready to leave your job behind.  Don't feel guilty about it.  Everything has a season and if your side hustle has blossomed into a thing - great!

Even a seemingly stable job can present some uncertainty.  What if there is no room for growth in your company?  What if something in your family has changed, like having to care for an ill parent or the arrival of a new baby?   What if clients start dropping like flies and you suddenly get laid off?  What if you’ve always wanted to work for yourself but you’ve talked yourself out of it time and time again?

If you’re ready to jump into the world of freelancing full-time, good for you!  According to the Bureau of Labor Statistics, there are 15.5 million self-employed people in the United States.  You’ll be in good company!  And that number shows no sign of stopping. By 2020, a separate study estimates that more than 40% of the American workforce, or 60 million people, will be independent workers—freelancers, contractors, and temporary employees.  That’s a lot of people!

Anything new and unknown is scary and exciting, all at the same time. But the more information you have, the better prepared you’ll be.  That philosophy applies to most things and it definitely applies to making the transition from side hustling to being a full-fledged freelancer.

So, what can you start doing right now to make a successful transition from time clock puncher to solopreneur?  Here are some tips to get ready for the big leap.

Get emotionally ready.

Freelancing is a whole new ball of wax.  For starters, there will be no one to report to.  You’re the boss!  You’re the decision maker, the human resources department, the sales department and chief bottle washer, all in one, like this Wells Fargo commercial so brilliantly demonstrates.


Freelancing can also get lonely.  There’s no one to shoot the breeze with about last night’s game in the staff lounge.  No more office birthday parties to look forward to.  No more baby showers.  If you thrive on a steady stream of high-fives and companionship, be prepared for a letdown.  One way to combat the loneliness is to network outside of your home office.  Join a local Meetup group to connect with folks who share your interests.  You never know where you might find a potential client or collaborator.  Also, consider grabbing your laptop and working from a library or a coffee shop occasionally.  The change of scenery will do you some good.

Face-to-face isn't your thing?  No worries.  There are a slew of Facebook groups you can join, like mine. Come on over - we'd love to have you!

Also, have confidence in your abilities.  There won’t be any more annual reviews with a supervisor for you to get praise and feedback so you will have to pump yourself up now and again.  Ask for testimonials from clients who are happy with your work then you’ll have permanent feedback that you can read again and again when you need encouragement.

Get financially ready.

You’ve probably gotten used to getting a paycheck every two weeks and it sure does feel good!  Well, news flash – kiss those days goodbye.  That’s not necessarily a bad thing, though.  Depending on how many clients you have, you might get paid several times a month, or get paid weekly or even daily!  But because you’re now responsible for setting your own rates and paying your own taxes, things can get a bit tricky.  That’s why it’s best to put some money aside, preferably three months’ worth of expenses before you tell your boss "adios."  That way when a client isn't able to pay, you’ll have something to fall back on.  Bills still have to be paid and I bet your utility company won't care that your client just bolted and didn't pay.  They just want their money!

Plus, as a freelancer, income can fluctuate.  One month may bring in some really decent income and the next may fall flat.  Take a look at your expenses and make some cuts, if needed.  You might have to slash your cable (*gasp*) or change what you buy at the grocery store.  Make a new budget that also includes paying taxes on your income.   If this kind of stuff makes you want to pull your hair out, consult a financial professional.  You don’t want to be hit with a big tax surprise at the end of the year.  Prepare now!

Get your family ready.

Have you talked to your family about leaving your job and becoming a freelancer?  No?  Well, that’s not good.  They'll be affected by your decision also so talk to them and get their input.  How do they feel about possibly having a temporary loss of income or making cuts in the family budget?  Have a family meeting and discuss the changes that could happen – you’ll be home more often but you’ll need time and space in which to work, there might be times when money is tight, things like that.  It’s best to get your family’s stamp of approval before making a sudden change.

When I started working from home, I sat down and talked to my boys.  They were thrilled that mom was going to be working from home but I had to make it clear that I was working.  Emphasis - working!  That didn't mean that we couldn't take breaks throughout the day and play a game or watch a show.  That's one of the reasons you wanted to freelance, right?  Now that they're older, they balance their recreational time and school stuff quite well, I'm proud to say. They know they have to handle their business before downtime.

Never stop learning.

I can't stress this one enough. Lots of companies provide continued education -- they'll pay for you to attend a class to learn a new skill.  Well, that's great because you know what?  It benefits them when you take that class.  You've now got a skill that you can use with that company.  As a freelancer, it's up to you to develop your own continued education plan.  I take at least one class every year and I highly suggest you do the same.  In the full-time world of freelancing, you're going to run across a lot of different technical systems, way more than just the one your office might have.  You won't be able to learn them all.

Recommended Courses

For example, if you want to offer newsletter management, it might be helpful to learn ConvertKit or Mailchimp (the biggies). Is Pinterest your thing and you want to manage Pinterest accounts for bloggers?  Cool!  I use Tailwind to manage Pinterest and Instagram accounts and they've got lots of tutorial videos.  Try it free for a month, get in there and watch some tutorials, manage your pins and boom!  You're on your way!

When it comes down to it, preparation is key to making a successful transition from side hustling to self-employment.  Get your ducks in a row and congratulations to you!  And if you need a group that totally understands what you're going through, join my private group for side hustlin' virtual assistants like yourself.  See you there!