Self Employment: 4 Challenges and How to Face them Head On

The tough thing about self-employment is that no two solo-businesses run exactly alike. Personalities, business models, and industries dictate different rules, expectations, and even challenges.

And you better believe there are challenges when it comes to being a one-woman show.

It’s tough to know who to turn to for advice when you’re working on your own. While everyone’s situations are vastly different, here are four common challenges solopreneurs face, and a few tips on how to handle them.

No coworkers

When you first became self-employed you probably expected a rise in your social life. Seeing as how you can set your own hours, you planned on squeezing in lunch with friends or afternoon playdates. However, that isn’t always the case. There may be times when you see friends, colleagues, and former coworkers regularly, but there will also be many seasons of being cooped up in the house or office with little social interaction.

So, how do you deal? There’s no one-size-fits-all option, but here are a few ideas: join a co-working space. Even if you only use it a few days a month, you’ll still get the camaraderie of an office environment. Participate in Slack channels or Facebook groups. Schedule weekly Google Hangouts with like-minded solopreneurs. Follow through on those lunch dates you were hoping to squeeze in with friends.

When worse comes to worst, work from the same coffee shop and get to know the team of baristas. Eventually, it will feel as they’re your real-life coworkers as you eavesdrop on their workplace drama. Plus, they may even begin to call you by name when it’s time to pick up your order.

No boss

No one likes a micromanager, and if you’ve ever had one in the past, you become leery of all future bosses. That isn’t to say your last boss was bad, but you were excited to have no one to answer to when you went off on your own. 

Now you’re there, and there’s no one to answer to. There’s no one nudging you, no one motivating you to get things done. Accountability falls on your shoulders, and yours alone when you’re self-employed. 

Similarly, when you’re dealing with difficult customers, you can’t move anyone up the chain, and there’s no one who has your back, except yourself. You’re the head honcho, and you’re the final say.

It’s important you be your own boss, bosslady. That means you need to treat yourself as an employee, too. Give yourself annual performance evaluations. Better yet, do it every four or six months. Measure your room for growth, set goals, and analyze if you’re meeting them.

Handle taxes

Are you rolling in the dough now that you’re working on your own? I’d love to give you tax advice, but I’m neither a seasoned tax professional nor am I a seasoned self-employed professional who loves to DIY her taxes. My advice? Set up systems such as Freshbooks or Quickbooks that can help you manage your accounting, invoicing, and tax preparation all year long. 

Also, find a tax professional who focuses in self-employment. You can get your taxes done by any accountant, but be smart and choose a one who knows your particularities. 

Bottomline: keep detailed records and pay your quarterly taxes.

Being Taken Seriously

I don’t have a company name. Well, that isn’t quite true, I’m doing business under my personal name. As a solopreneur and freelance writer, it works. However, when people ask me where I’m currently working, and I tell them I’m self-employed, the next question they always ask is what my company is called. < Insert awkward silence here > 

If you’re in my shoes, remind yourself of this: You can do business under your name for as long as you’d like. In fact, many people who “made it” as a solopreneurs actually end up trashing their business name to work under their own personal name instead. They become their own brand.

If you’re facing a situation where someone doesn’t take you seriously for the hard work that you do, channel your inner Beyonce. As she says, “I don’t have to prove anything to anyone, I only have to follow my heart and concentrate on what I want to say to the world. I run my world.”

It’s time for you to run yours.

What other challenges have you faced in your career? How did you handle the ups and downs of owning your own business? Let me know in the comments.  


Erin Ollila graduated from Fairfield University with an M.F.A. in Creative Writing. She believes in the power of words and how a message can inform – and even transform – its intended audience. Her writing can be found all over the internet and in print, and includes interviews, ghostwriting, blog posts, and creative nonfiction. Erin is a geek for SEO and all things social media. She lives in Southeastern Massachusetts, neighboring Providence, Rhode Island, one of her favorite small cities.