Freelancing? What I Wish I Knew Before I Started

Vacation time, unlimited. Working in your P.J.’s, yup. Zero commute, check. Sounds rad, right? Maybe, but then again, there’s more to it!

Working as a freelancer sounds awesome and in many ways, it is. But, there is a ton of downside as well. From instability of hours, consistent work and of course steady income, to increased stress (surprise) and unexpected loneliness, freelancing isn’t as glamorous as it looks on social media. So, today I’m giving you the need to know dirt from people who’ve been there and done that.

I’ve interviewed four ReResumeMe Career Coaching clients, each of whom freelance or started their own company. Here’s a candid look at their thoughts of being on their own and what they wish they clearly understood before they left behind their steady paycheck.

Challenge, what challenge

“Working as a freelancer reminded me of the movie Groundhog Day” Gavin R. Austin, Texas Former IT Consultant

Before I started my own IT shop, all I heard was going it alone is so challenging; so rewarding. So, I thought ok, let’s do this. I love challenging work and projects! And, when I first launched as a freelancer, I was pumped!!

It was an easy transition at first. I had a lot of potential clients that I considered to be low hanging fruit. I knew them from past positions, they knew my work and I knew they’d hire me for IT projects. It was easy to begin my business and money flowed in. I had complete control over my schedule and I loved it!

The problem came when I realized what being a one-man show meant; my bandwidth was stretched super thin. Since there was only one of me, I was stuck doing the same type of projects over and over. I couldn’t expand my service offerings, because I couldn’t manage the workflow and challenge that unique projects would bring. Yet, I wasn’t making enough money to hire someone else or even sub out work.

My job became a vicious cycle of the same type of work, day in and day out. I couldn’t hack it (no pun intended). I needed variety and challenge. So, I turned to the team at ReResumeMe to get back to a normal 9-5 and I am glad I did.

Tax Burden and Unreliable Income = STRESS

“When a giant tax bill landed in my lap, I freaked out!” Claudia W. Boston, Massachusetts Sales Trainer

I hated my job and new I could strike out as a consultant and simply mimic what my employer offered their clients and make it on my own. So, I did just that and it worked! I was super successful. So much so, that after 9 months of being on my own, my old boss reached out and asked me to freelance for them. I controlled my hours, client list etc. and could still take on my own new clients. What’s not to love; I signed up immediately.

As I anticipated, HR reached out and asked my to sign a ton of paperwork, including a few tax documents. I knew there’d be paperwork, but why tax documents? I didn’t really work for them. It was explained that as a consultant, taxes still existed. Duh, I thought; of course, they do. Oh well, onward and upward I thought. Until tax time came when I received a giant tax bill because I hadn’t withheld taxes or properly reported income from the work I had taken on. I freaked out, called my mom crying and had to hire an accountant ASAP!

I learned the hard (and expensive) way, that there’s more to freelancing than working hard and collecting a paycheck. This may sound stupid to some, but for me it was new info. The tax burden, both the expense and management of, as well as the unreliable income stream from consulting work, caused me to rethink my decision to freelance and run back to my steady job.

I Missed Happy Hour

“I desperately missed being part of a team, going to happy hour and simply being around smart people I could learn from.” Kali. J. Miami Beach, FL. Marketing Director

After 12 years climbing the corporate ladder, I decided to strike out on my own and open a marketing firm. I use the term firm loosely, because my “firm” existed of me and my dog!

In the beginning, I did very well and the transition to working for myself and by myself was easy at first. But, I slowly lost focus and motivation. I found myself sweeping the pool, pulling weeds and doing laundry instead of working. I realized I was allowing everyday life to get in the way of my productivity. No matter how hard I tried, I couldn’t get back into the game.

After reflection, I realized why. I was lonely and bored. Sure, I talked to a ton of clients every day, but I missed being on a team. I missed sharing the excitement of landing a big client over drinks at happy hour. I missed brainstorming on marketing ideas with really smart people. And, as crazy as this sounds considering Miami traffic, I missed the commute which gave me time to decompress before heading home at night. I wish I had known how lonely consulting would be before I left behind a really awesome job and coworkers. And the end of the day it was a great experience, but I am glad Jeanna and Michael at ReResumeMe helped me get back into the corporate world.

I Lost Professional Traction

“I realized my career was going nowhere, fast and that social media sucks” Mike C. App Creator, Indianapolis, IN.

I had a great job in Chicago. I lived downtown, road my bike to work (when it wasn’t snowing) and pretty much had everything going for me. Until I got this wacked idea to leave it all behind, move closer to my family and head back to Indy to become a Co-Founder in my buddy’s start-up.

Honestly, I didn’t know what to expect from the decision, but I thought it was the smartest move of my life at the time. My friend and I worked our asses off to launch our business and we were successful in getting the company off the ground. We were on top of the world!

But then reality sat in. We built a decent business and held our own, but we didn’t have a Mark Zuckerberg idea that would change the world. We simply had a business. Sure, I had flexible hours, if you consider 12-14 hour days and working weekends flexible, because that’s what it took to keep the business moving forward.

As I stalked my fraternity brothers on IG and Twitter, I watched them become VP’s, Directors and Officer level big shots, while my buddy and I sat idle. Our friends were presenting to the board and we were sitting in our tennis shoes and shorts wearing every hat imaginable; we were simply trudging through our days.

I realized what I thought we were building in the beginning was nonexistent. We weren’t going to be bought out, go public or make the news. It wasn’t days spent on yachts with champagne and caviar. It was frozen burritos, long hours and one client loss away from utter financial ruin. Taking a vacation was impossible, because we were “on” all the time. One day I decided I couldn’t tread water anymore; I decided to go back to a regular job.

But, the problem with that idea was I had lost professional footing. I couldn’t walk into a VP role. I’d been out of the game for four years. I wasn’t up to speed on the market trends, newer technology and certainly couldn’t compete in an interview with someone who hadn’t taken a hiatus. Ultimately, I lost traction and forward progression in my career. Had I stayed in Chicago I’d easily be at the VP level, but now, I had to take a major step back to rejoin the professional world. Which I swallowed and did.

At the end of the day, I learned a lot about owning and running a company. I also learned that social media sucks and life as an entrepreneur isn’t all it’s cracked up to be. I’m happy to be out of the rat race and back to life as a corporate ladder climber.

Ok, Now What

Look, this wasn’t meant to squash your dreams if you’re seriously considering freelancing or starting a business. It’s just a reality check. We coach clients every day on how to start a business, begin as a freelancer or manage a side hustle. And, while a lot of people find success, just as many don’t.

If you’re weighing your options and trying to decide what your next career move should look like, tap the team at ReResumeMe and ask that boss, Jeanna McGinnis coach you through it. She’s started successful businesses and knows what it takes to make it. She’ll help you determine if you’re ready for it or not. Thanks for reading! – Michael

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About The Author

A self-proclaimed foodie and wine snob, Michael is part of our Operations and Customer Service Resume Writing and Career Coaching team. Michael prides himself on helping our clients improve their job search results and develop robust career plans. His creative mind allows him to step outside of traditional resume writing boundaries to create compelling resumes and professional correspondence for ReResumeMe clients. If you’d like to simplify your career, follow Michael and the rest of our team on Twitter and LinkedIn to get updates on careers, job search and resume best practices!