You asked: How do you make the jump to full-time freelancing?

4 min read
Shayna Hodkin
  •  Jun 9, 2017
Link copied to clipboard

Editor’s note: This is the second post in our new advice column (read the first one). Have a question? Ask it here—it’s completely anonymous.

Fake it ’til you make it

After 4 years in the workforce, I saved up enough to go on an around-the-world backpacking trip. It was a dream: pasta in Italy, climbing in Peru, camels in Jordan, the whole thing. But now I’m totally broke. I’m ready to start working again, but I feel “priced out” of networking—I know where the hotspots are in my city, and everyone tells me to invite people in my field out to coffee to pick their brains, but my bank account is exclusively rocking zeroes right now.

It feels like in order to make a lot of money, you have to already have a lot of money. How do I get out of the broke cycle and back into the workforce?

–No Dollars in NorCal

As far as I’m concerned, my high school economics class could have been summed up in 3 words:

Money makes money.

We live in a bizarre universe where if you have money, it’s really easy to make more money, but if you don’t have money, you end up losing money. Overdraft fees are a good example: You are quite literally paying for the privilege of being dead-ass broke.

Image: Unsplash.

So now you’re at a point in your life where you want/need to see and be seen. But without money to get around, you’re stuck.

To get going again, you have 2 options:

  1. Take a job you don’t want so you can make money to pay for things that will hopefully get you the job you do want
  2. Fake it ‘til you make it

If you choose to go with option 1, you’re taking a very big risk. Because, like being broke keeps you from making money, being stuck in a crap job has a way of sucking away at your energies—and therefore keeping you from moving forward. So, while you might enter with the mindset of, I’m only here until I don’t have to be here, there’s a big chance that you’ll end up there for a lot longer.

So, against the advice of my accountant and my mother (different people): You’ll have better luck with option 2.

Elizabeth Wurtzel, the author of Prozac Nation, wrote a NY Mag piece about feeling “behind” in the life game. Regarding savings, she wrote,

I believe if you take care of the luxuries, the necessities will take care of themselves.

And I really, genuinely believe that’s 100% true. At least from how I’ve lived.

Hey, Internet, I’ve been so broke. Broke like one time, my debit card didn’t swipe for laundry. Broke like, I really straight up couldn’t pay for things at all.

But I still had to present myself to the world. So, here’s what I did:

I took up expensive-seeming interests and hobbies.

I’m vegan, I brew kombucha, and I make my own perfume. These are things that sound very ~fancy~ but in reality they save me so much money. Find a few things that sound super bougie but are actually money-savers—these activities are usually of the DIY/crunchy granola variety—and run with them.

You already have something going for you: stories from your trip. Speak loudly about them. You will seem cool and successful and cultured, even if you’re barely paying rent.

“Fake it ‘til you make it.”

Twitter Logo

I spent an inadvisable amount of money on one pair of shoes and 2 lovely dresses.

Don’t go into credit card debt. Don’t go into credit card debt. Don’t go into credit card debt!!!! But do find a way to buy a nice shirt or 2 so you can look presentable. Invest in looking respectable, for the same reasons you wouldn’t release an undesigned portfolio site with great work samples: because you know (we all know) that content is judged alongside its presentation.Twitter Logo

I stopped doing expensive things.

There are really expensive things that we do and they are so ingrained in our day-to-day that we forget how expensive they are. So, first things first: stop drinking.


Drinking costs bank. It’s not just the money you spend on alcohol—it’s the ill-advised munchies, it’s the cab home when you can’t/shouldn’t drive, it’s the Amazon Prime binge.

Very little frustrates me as much as meeting a friend for sushi only to listen to them tell me how broke they are. Write up an honest budget and figure out where your money is disappearing. Stop eating sushi. Hang out with your friends at home. Read a book. Watch dog videos on YouTube. Do things that are less expensive than what you’re doing now.Twitter Logo

Also, according to Vice, sobriety is cool now. Drinking soda at the bar is probably the cheapest way to look hip if you absolutely *must* leave the house.

Looking champagne when you feel beer is kind of like 2 kids standing on top of each other under a trench coat—you look like a functional adult while you are actually a stressed-out babychild. It’s like personality dress-up. Enjoy your secret.

You can also resort to the broke person’s savior: The internet. For every Meetup group and neighborhood hotspot, you’ll find 4 Facebook groups, subreddits, and Quora threads that will help you meet people in your field. Especially with the growth of remote teams, use the internet freely to meet people and socialize.

After all, anyone who grew up with AIM and chat rooms can confirm: The internet is a great place to be someone you’re not.

powered by Typeform

Panic! At the thought of full-time freelancing

I’m not 100% happy at my current job, and sometimes I feel like I’d do much better as a full-time freelancer. Still, I’m really scared of not finding enough clients, or just failing in general. Do you have any advice for taking that leap?

–Future Full-time Freelancer in Fresno

Don’t be scared. That’s my advice. Godspeed.

Okay, there’s more. But that’s the TL;DR of it.

Wayne Gretzky definitely did not say this, but it’s still quotable: You miss 100% of the shots you don’t take.

When you hold back from taking risks because you’re afraid to fail, then you’ve lost the big life game. Risk-taking is a 0:1 binary: either you did it, or you didn’t.Twitter Logo When fear holds you back, you come out 0.

If you’re more scared of losing than you are of failing, then freelancing is a definite go. But just because you’re willing to take a risk doesn’t mean you have to go in blind.

“When you work for yourself, you have the unique opportunity to build your own niche.”

Twitter Logo

The 2 biggest struggles of freelancing are finding clients (duh) and working not from an office. We tend to forget about the latter because we’re so concerned about the former, but once we have clients, it’s so easy to mess up because we haven’t figured out how to deal with them.

So, while you’re still full-time employed, use this time to practice. Start networking, whether online, at Meetups, via friends, or whatever. Scope out potential clients and start Facebook stalking freelancers in your field. Join all of the Slack groups! Be everywhere you can to meet all of the people you would want to pay you to do things when you’re ready.

A really nice guide to this lives on the nuSchool’s blog (full disclosure: I helped write it).

While you’re doing this, ask your boss if you can start working from home every so often. If they agree, you can start figuring out what works for you. Do you work better with music or in silence? Does your house need to be clean, or can you work with a cluttered desk? Are you a coffee shop kind of human? Would you do better with a pet?


If they don’t agree—well, you were planning on leaving anyway. Start Pinteresting dope home office setups and use your weekends to DIY the pants off of your new work corner.

Or scope coffee spots. Whatever you’re into.

Also, while you’re still working, start saving money. As a freelancer, there is literally nothing more valuable in the world than a savings account. We live in an unstable world! You might be the best person doing the thing you do, but sometimes you’ll be waiting for clients to call and all you’ll hear is crickets. Especially at the beginning of your career, having a safety net will make your risky decision feel much more secure.

If this makes you feel better, I am of the opinion that in the world of careers, being self-employed is the safest thing you can do.Twitter Logo

As the child of 2 self-employeds who are both the children of self-employed, freelancing is in my blood, but I’ve also been able to see the ups and downs of living your business. Sometimes business will be slow and you won’t have a lot of money. Tough. But you’ll never be laid off, and you’ll never be replaced.

When you work for yourself, you have the unique opportunity to build your own niche. You can take projects that speak to you and your career goals. You can take classes and build your skill set at your own pace.

For better or for worse, you’re entirely responsible for yourself.

The side effect of freedom is fear—if you’re willing to put up with that.

Ask a question

It’s totally anonymous. Just ask here.

You’ll love these posts, too

Collaborate in real time on a digital whiteboard