• Lifestyle, Advice

The biggest lessons I learned in the first 6 months of freelancing

This is a post from a member of the Freelancers Union community. If you’re interested in sharing your expertise, your story, or some advice you think will help a fellow freelancer out, feel free to send your blog post to us here.

In late spring of 2011, I became a freelancer. By early December of 2011, I'd returned to cubicle life. Some may deem that a failure. But rejoining the full-time workforce was, hands down, the right decision. Still, I never forgot what succeeding as a business owner would take. I thought, “Someday, this will be my career path.”

Fast forward eight years and that someday is today. (Technically speaking, someday was in January.) This time around, I’ve devoted countless hours to learning the art of self-employment. The investment has spared me from mistakes small and large.

But no learning plan accounts for everything. Transitioning from 12 years in corporate settings to a solo venture requires adjustment. Over the past six months, the most interesting lessons have been the ones I never saw coming.

Lesson #1: Use a real alarm clock and keep your phone out of reach

Full-timers assume that the greatest thing about freelancing is waking up whenever you want. I submit it’s also the worst.

Starting the day with no set schedule is one thing. But staying awake in bed for an hour every morning because I wouldn’t put my phone down created a real problem. My late starts often left me working past dinner and sacrificing evenings. After a few months, I knew nothing would change until I fell asleep and woke up away from my phone.

In the recesses of my closet I found a 15-year-old LED alarm clock. I plugged it in, replaced the back-up 9 volt, and never looked back. My phone charges on a dresser out of arm’s reach but close enough to answer an emergency call. As a bonus, I’m reading before bed again and falling asleep sooner.

Lesson #2: You don’t need every piece of tech imaginable

In my younger and more vulnerable years, I read a bit of personal finance advice that stuck. The writer suggested to delay luxury purchases for two months. At that point, the desire is either long gone or has steadily grown.

Investing in a semi-professional microphone for podcasting seemed absolutely necessary not long ago. I had zero bookings to interview on a podcast, let alone solid plans to start my own.

Within a few weeks the urge passed. As of today, I’m happily microphone- and podcast-less. That’s not to say I haven’t upgraded my office setup. After impatiently waiting the full two months, I pulled the trigger on a 32" UHD 4K monitor. The time I’ve saved no longer toggling between multiple windows more than covers the cost. In my book, that’s money well spent.

Lesson #3: When it’s your business, strong passwords matter

All my login credentials lived in an offline spreadsheet. Four, maybe five, passwords comprised my heavy rotation.

Miraculously, I’ve lived to tell the tale of poor password habits unscathed. Before self-employment, using strong passwords and managing them properly wasn’t a goal. It was a happy accident. But going solo involves signing up for numerous sites you’ll want to separate from your personal life. Login credentials relate directly to your bread and butter. You’ll want to ensure that they’re as secure as possible.

For me, that meant finally using a password management system. Once all these new business logins were securely stored in one place, I reset all my weak passwords. Now I have peace of mind after years of intermittent worry. Plus, never having to remember credentials is priceless. Everything’s right there whether I’m on my computer or phone.

Lesson #4: If the conventional wisdom doesn’t feel right, it probably isn’t

98% of the advice I’ve received in my professional life has been spot on. Incorporating this constructive feedback isn’t easy, but it’s given me an edge. Then there’s the remaining 2%. It’s rarely flat-out wrong. In fact, peers you admire may swear by it. But something’s off. Maybe it doesn’t reflect your personality or goals.

Doubting popular, proven consensus feels wrong when you’re new to the game. If a recommendation genuinely doesn’t work or feel right to you, don’t force it. Ditch it.

My moment of defiance came early. Many freelancers take strong measures to limit calls with clients or prospects. I get it. We’re all busy, and the last thing the world needs is yet another pointless meeting.

I’m not volunteering for calls, but I’m more than willing to chat. One-on-one conversation comes naturally to me. It’s how I’ve forged strong business relationships, some of which have blossomed into lasting friendships.

Yes, it’s arguably not the best use of my time. Some calls have ended up going absolutely nowhere. The truth is I don’t care. Maybe I’ll think differently once I have a larger client roster with projects booked out months in advance. Until then, I’ll gladly make time to talk.

Lesson #5: Errands are your friend

During my corporate days, I changed into PJs within two minutes of coming home. Going anywhere after work was a drag. Why people socialized on weeknights baffled me. Now I relish evening grocery store runs or mid-day walks to Walgreens for a few necessities. My online shopping for household staples is non-existent.

Getting out of the house is a privilege, not a chore. To keep from falling victim to hermitude, find small tasks you could use Postmates for but prefer doing in the real world.

Every day I step out for a walk around the block. (Even during Chicago winters, there’s plenty of snow to shovel or ice to salt.) On the rare occasion I have something to mail, I drop it in a collection box five blocks away.

It’s not much, and that’s the point. A few extra errands and walks strike the right balance for me. It keeps me a little engaged with the community outside my four walls.

Lesson #6: Routines take time and experimentation to nail

My schedule is far from set. Or far from where I thought it would be by now. I figured I'd find my groove within a couple months. In reality, I stopped observing the "no meetings hours" I’d set on my calendar within two weeks of adding them.

If you’re not willing to reschedule a meeting request that interferes with blocked time, your calendar isn’t a calendar. It’s a recommendation. Your schedule won’t work until you take it seriously. You can become rigid, adhering to your regimen no matter what. Or you can question why it’s not working and try something new.

Keeping my time organized and predictable felt like the key to success. In reality, continuously adjusting what’s not working is more important. In this case, growth trumps consistency.

It turns out many solo business owners take a year or 18 months to find their rhythm. I’m giving myself some leeway. And I’m always trying new approaches to budgeting my time.

In conclusion

This second foray into self-employment has been worlds different. Instead of signing an offer letter six months in, I’m growing my business and helping fellow freelancers.

My planned learning will never stop. But in all honesty, I’m more eager to see what unexpected lessons come next.

Jesse Butts is a writer, marketing consultant, and founder of Calque Marketing. You can find him at