07/ 15/ 18

5 Tips for Transitioning into Freelance Life

I made “the leap” towards self-employment last June, and I can wholeheartedly say it’s one of the best decisions I’ve made in my entire life. I have work-life balance (yes, it exists!), yet I’m getting more work done than ever. Most importantly, I’m genuinely happy every time I sit down to do work — so much so that I oftentimes wake up earlier than I need to, my body buzzing with excitement just thinking about opening up my laptop. Major nerd alert, I know.

It’s common knowledge that freelancing brings a slew of benefits like flexible hours, being able to work remotely, and having the satisfaction of being your own boss, but here are some of the less obvious gems I’ve discovered working for myself over the past year:

You get hours back in your day by eliminating the typical work routine.
When I lived in San Francisco, I’d spend up to
five hours each day getting dressed, putting on makeup, and taking the shuttle to and from work in the South Bay. Oof. It was better here in Denver — my commute was about 30 minutes, making up a work routine of about two hours.

Now that I work for myself, I don’t have to commute or make myself look presentable (lol), giving me precious hours back in my day to do whatever I please. These days, I take 30 minutes in the morning to do my desired routine: meditation, tarot card reading, and fixing myself a healthy breakfast. If I’m particularly eager to get to work, I can be up and running just 10 minutes after I open my eyes. And once I’m done working, there’s no need to commute back home, leaving me with extra time and energy that was previously consumed by the 9-5 grind.

There’s no pressure to appear a certain way.
Fewer words make me want to barf than the word “optics”. I think American work culture puts too much emphasis on what you look like at work, as opposed to considering how much value you’re actually bringing to the company.

On my proudest days, I’ll start working at 8am, bulldoze through my to-do list, and emerge from my work flow to realize it’s 3pm, yet I’ve already completed everything I set out to do. At a traditional work environment, I would’ve stayed tethered to my desk until 5pm, fearful of what people might think if I dip out two hours “early.” Now, I’ll happily stop working when I finish my work (what a concept!), and reward myself for being so productive by doing something fun — no matter what time of day it is.

You become the gatekeeper of your own success.
When I was working for other people, I never successfully negotiated a raise, and I was never paid more than an entry-level salary. It was frustrating, and made me feel terrible about my self-worth.

Now, I determine how much I’m paid. I decide if I’m ready to move up to the next level. If I want a six-figure salary, I have the authority to go out and get it — and nobody can tell me I’m not worth it.

Laptop and croissant at a Parisian cafe

My desk while working remotely from Paris!

So yes, working for yourself is pretty dope! If self-employment sounds like something you’d enjoy too, read on to see how you can set yourself up for success as you venture off on your own. 

Here are five practical tips for transitioning into freelance life:

  1. Determine if your personality is a good fit for self-employment.
    Freelancing is not for everyone. You won’t have a boss telling you what to do, and you won’t have a steady paycheck (at least for the first six months or so). The initial transition period can be an emotional rollercoaster, and you likely won’t have work-life balance while you’re hustling to set up your business — especially if you’re still working at your 9-5. Are you a determined self-starter who is comfortable “figuring it out as you go?” Are you okay with the unknown and can you persevere through instability? Are you intrinsically motivated to succeed? If you answered “yes,” to these questions, you’re likely a great fit for freelance life!
  2. Make a transition plan.
    “Taking the leap” can feel more like baby steps if you commit to a solid plan and execute regularly. Create milestones for: saving money (I was cool with two, but people typically save up three months of living expenses before quitting their 9-5’s), setting up your new freelance biz (your business checking account, your LLC, and your services as a freelancer), and transitioning out of your 9-5. Putting dates on milestones will motivate you to get shit done.


    For the risk-averse aspiring freelancer, you can also start taking small freelance clients while you’re working your 9-5. Then, you can quit your 9-5 once you’re ready to make freelance full-time. Be sure to establish a goal for this as well (e.g. I want to bring in $2,000/month with freelance work before quitting my 9-5).
  3. Solidify your offerings as a freelancer.
    What services do you have to offer, and what do you want to charge? Sit down with fellow freelance friends to pick their brains on how they package up their services. Look at the websites of people in your field. Sign up for Upwork as client (not a freelancer) so you can browse freelancer profiles and see what they charge. You will constantly tweak your services and pricing once you’re out there, but you want to ensure you have a strong online presence that clearly states your services when you launch.
  4. Reach out to your network.
    Once you’ve officially launched, tell EVERYONE you know. While you can get gigs from freelance sites like UpWork, word-of-mouth referrals from people you’ve worked with in real life undoubtedly brings the best, highest-quality clients. 
    Email your network with customized messages about how you can help their particular businesses succeed. Post your announcement to community Facebook groups and Meetups. Attend networking events and pass out your business cards. As a freelancer, you are also officially in sales — and the more selling you do for your business, the more clients you’ll get.
  5. Find your freelance people and resources.
    Starting a freelance biz also brings in a set of new challenges: How do you write a client proposal or contract? How do you plan for your taxes? How do deal with a difficult client who is months late in paying you? Luckily, these are all challenges that have been thoroughly documented online, and that many people have overcome before. Do your research before tackling a new problem, and identify a few friends that you can turn to for advice. Overcoming these new hurdles will be a breeze with a solid support network by your side.

There is so much more to say about getting your business off the ground as a freelancer, but I hope these tips were a good starting point as you embark on your freelance journey. Did I miss any important tips? Let me know in the comments below, or connect with me on Twitter @katerinajeng. Good luck!





Photo of Katerina Jeng, author at Scratch The List

Hello! I'm Katerina, and I'm on a quest to complete my bucket list. Follow along for travel stories, happiness tips, and inspiration to make your life worthy of your dreams.

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