How To Transition From Self-Employed Back To Full-Time

Image via Flickr
Image via Flickr

At this time last year, I was working for myself and had just gotten back from a lucrative trade show in Las Vegas. Our custom phone case making equipment was selling as quickly as we could keep it in stock, and we were crossing $160,000 in revenue in less than one year of being in business.

Revenue had been growing at a steady rate for the last year, and my business partner and I were beyond excited at the prospect of being sustainably self-employed at the age of 24. Little did I know that just a few months later, I’d be making a very difficult decision to return to full-time employment.

I had been doing freelance content marketing on the side to help augment my income, while we focused on keeping funds in the business and reinvesting in new inventory. Interestingly enough, over 331,941 Americans also freelance on the side of their full-time jobs.

However, splitting my efforts and working an easy 70-80 hours per week was rapidly becoming less and less sustainable for the results we were seeing with our company. My performance was suffering for both my freelance clients, and with my own business. Something had to change.

When we took a hard look at the numbers, we simply weren’t generating enough profit to sustain two people’s lifestyles. It was the perfect amount of income to support one of us, but not both. As an entrepreneur who never wanted to work for someone else again, this was a big pill to swallow.

So, I made the difficult decision to take myself out of the business, move to San Francisco (to work at CreativeLive!), and start a new adventure.

It wasn’t easy, and a lot of lessons have been learned along the way. From learning how to create a product nobody wanted, to learning how to discover my strengths as an entrepreneur, and avoiding getting fired while starting a side business, I’ve done it all. If you’re in the same boat – or maybe just considering making the shift back from freelance to full-time – here are some of the lessons I learned. Maybe they can help you along the way.

1) Choose a Job That Inspires You

Coming from working for myself and being intrinsically motivated to do my absolute best on everything, this was absolutely imperative.

If I’m going to be investing 50-60 hours of my time each week into building somebody else’s product, I needed to be absolutely certain that I was in love with the product and mission of the company. Luckily for me, I landed at CreativeLive where I get to help other talented entrepreneurs around the world reach an audience of people who are motivated to learn and improve their lives.

When you choose your first job out of being self-employed, don’t just settle for the first opportunity that comes your way. Pick something that’s going to challenge you, motivate you, and help you get to where you want to go next.

your art is boring

2) Focus on Building Your Core Strengths

Since you’ve been out on your own, you know how hard it is to launch and grow a business into something that can sustain your lifestyle. It takes an impressive amount of skill, knowledge in your industry, and a meaningful network to leverage in getting your business off the ground. Because my goal is to eventually get back to working for myself, I very consciously chose a type of company and position to go after that would allow me to essentially get paid to become better at the skills I’d need to strike out on my own again.

3) Work Less, Live More

With your new job, you’re (likely) no longer solely responsible for the success or failure of the business you’re in.

Don’t immediately burn yourself out by putting in the number of hours you were doing at your own company beforehand. Yes, still work hard and help take your team to new heights, but learn how to bring balance back into your life. You’re here to contribute, learn, and be part of building something great.

Justin Barker, one of my former co-workers here at CreativeLive learned an incredible amount about working hard and living more. Now he’s back to freelancing, and loving it.

4) Set Realistic Expectations for Yourself

It’ll take time to adjust into your new role, and your employers (should) know that. Don’t expect to move mountains in your first few weeks of work while you get used to your new product, teammates, and goals you’re being measured against.

Re-learn how to effectively work against the goals that now matter most in your job, and develop a system that’ll help you feel like you’re getting wins and making meaningful accomplishments early on.

freelance to full time5) Keep a Passion Project on the Side

If you’re like me, then you’re already thinking of the next business idea that you want to get started on. Having an outlet to express your creativity outside of work, validate your business idea, and learn what your next venture is going to be, is essential to remaining sane–you can even start freelancing on the side again if you set appropriate boundaries. Be careful not to let your side project interfere with your performance at work.

This transition, while very beneficial in many important aspects of my life, was very difficult. It was hard to come to grips with the reality that I had failed, to some degree, to achieve the goals I had for myself. However, that experience taught me more in one year than I learned in two years of working before I started that business.

What’s important is that I kept moving forward, and in doing so, I’ve discovered new passions, honed my skills, and have become much better equipped for my next venture.

Ryan Robinson FOLLOW >

Content marketing consultant to the world's top experts and growing startups. Online educator at where I share business advice and teach entrepreneurs how to start a blog and other side businesses. Check out my post on the best business ideas, read about how I validated a business idea in just 30 days, get my recommendations for the best business books, and check out my favorite motivational quotes.