Jessica Lawlor

Before I started JL&Co, when I only daydreamed about what it might be like to be my own boss, I often envisioned the following scenarios:

• Waking up slowly, no pesky alarms, places to be or bosses to answer to
• Working remotely from an exotic destination, sipping on a fruity drink, casually answering emails
• Going to a mid-day yoga class because why not?
• Taking a late afternoon nap when I feel drained
• Being paid to travel the country to speak at events
• Working from coffee shops, wineries, beaches, yoga studios, airplanes, etc.

The good news? The above scenarios are true. I’ve done all of ’em and yep…these are all wonderful perks of being your own boss.

However, these perks don’t come without a price.

Here’s the truth: running a business isn’t always sexy. 

In fact, a lot of the times, it’s downright ugly. 

That’s why I’ve made it part of my mission to share my entrepreneurial journey so transparently. I aim to be honest and open about my struggles because I want to give others a realistic look at what it takes to run a business.

Settle in for some real talk. Here are seven things that really suck about running a business, plus steps I’m taking to “ease the pain.”

1. It can be lonely. Like, really lonely. 

Hands down, the hardest part of quitting a full-time job to start a business has been experiencing loneliness. 

This downside didn’t fully hit me until the fall. That’s because up until August I lived at home with my parents, my brother, my pup and my cat. No shame — I strategically chose to live at home until I felt steady enough in my business to justify dropping $1,000+/month on rent, utilities, etc. 

When I lived at home, there were people around all the time. I always had someone to talk to or an animal to snuggle with. I appreciated the times no one was home because it meant true peace and quiet to get work done. 

Now, I miss the crazy!

These days, I work from my lovely two-bedroom apartment with a gorgeous office (sounds amazing, right?) yet sometimes I resent this space because I’m here all. the. time. There are days that go by where I don’t speak out loud to a single human being during the course of my work day.

The quiet can sometimes feel deafening. 

How I’m trying to ease the pain: 

• I try to get out of my apartment at least once every day. I teach yoga a few mornings a week and on the days I don’t teach, I try to practice, so I at least get out of the house, move my body and see other humans. 
• I’m collaborating and connecting with other entrepreneurs. 
• I go to my parents’ house a few times a month and work from there, just like the old days.
• I’m considering checking out a coworking space — not permanently, but maybe a couple of times a month.
• I’m part of different online groups for business owners, my favorite being the Solo PR Pro group ,where I feel I’ve found my people who get exactly what I’m going through.

2. You actually might miss that inane water cooler chat.

Know what I miss most about my old job? 

Saying hello to the folks at the front desk as I breezed by in the morning, coffee in hand.

Chit-chatting (and even venting!) with my coworkers and sending each other funny emails, videos or GIFs throughout the day to keep us going.

Crazily, I even miss the 15 minutes of wasted time at the beginning of each unnecessarily long Monday morning staff meeting spent dishing about Sunday night TV or the weather over the weekend. 

It sounds silly, but I miss these things. The parts of our day where we take a breather. Where we laugh. Where we say hello or connect.

How I’m trying to ease the pain:

• Twitter helps. Twitter is my water cooler — I check in a few times throughout the day to chat about those things I once talked to my coworkers about.
• I listen to podcasts. All the time. If I’m in my apartment and I’m not working, a podcast is on. I listen while I cook, while I do the laundry and even while I shower. It makes me feel like I’m “part” of a conversation. 

3. Thrive on praise? Now, you need to create it yourself.

Sorry if this sounds “millennial” of me, but I thrive on praise.

When I was in a full-time job, I became accustomed to being told I was doing a good job.

Of course, I accepted criticism when it was offered, but in general, that “Nice work!” or “Your presentation was buttoned up” or “Great media hit!” from my boss went a LONG way. It kept me going. It kept me motivated.

That doesn’t happen as often when you’re the boss.

Of course, from time to time, clients share praise (and it is *always* appreciated) but I also understand that’s not their job. They pay me to perform a service; they don’t have to be invested in my level of motivation or professional growth, as a boss at a 9-5 might be.

How I’m trying to ease the pain:

• I hang on to that positive feedback when I do get it! I have an email folder called “warm fuzzies” where I drop nice notes from clients or members of the blog community. When I’m feeling down or need a pick-me-up, I browse through the folder.
• I share my wins with my team member. Bringing a team member on board has helped me to find someone to celebrate success with!

4. The financial/legal side of running a biz is no joke.

Listen. I studied communications in college because I’m BAD at math. Really bad. Like, needs to use a tip calculator every single time I go out to eat, bad.

Now, I run a small business. And there’s a lot of tasks required that I file under, “Wahhhhh, this is hard. I want to hide under the covers and avoid these things at all cost.”

Invoicing clients. Figuring out how to price services. Taxes. Health insurance. Filing for an LLC. Trademarks. Budgeting.

Running a business is half doing the work you love to do and half dealing with all this other crap.

Messing up my quarterly taxes in my first year of business? A costly mistake. 

Paying an exorbitant amount of money each month to ensure I can go to the doctor? Not fun. 

Figuring out how to save money for retirement when no one is offering me a matching 401K? Confusing.

How I’m trying to ease the pain:

• I hire professionals. Plain and simple. There is no point in DIY’ing something that is incredibly important to the financial success of your business, not to mention your sanity. I’ve come to grips with the fact that sometimes you have to spend money to make money. I consider these professionals an investment in the future success of JL&Co. 

5. You learn to get comfortable with being uncomfortable — the uncertainty is real.

Last October, my business made more than $10,000. I felt like a baller.

The next month, my biggest client, accounting for nearly 22% of my total income dropped me with no warning. That was a rude awakening.

Ups and downs. Ups and downs.

You can never truly rest when you run a business. When things are good, that’s great, but that doesn’t mean they’ll be good forever. When things are bad, you need to get moving quickly to get back on track.

Each month, I anxiously calculate my income, always hoping to grow and earn more than the month prior, but coming to terms with the fact that this isn’t always realistic. 

How I’m trying to ease the pain:

• There’s no real way to get better at this except to embrace it. Learning to get comfortable with uncertainty has been humbling. It has also taught me to be nimble — to adapt and pivot quickly. 

6. You may lose sight of your passions.

Probably the most surprising pitfall of all, somewhere in my building my dream career, I lost sight of my passions.

When a friend asked me to name my hobbies last month, I was dumbfounded. Prior to starting my business, I would have immediately blurted out, “Blogging and yoga!” These are still hobbies of mine, but they are also now part of my career.

That makes them a whole lot less sexy.

How I’m trying to ease the pain:

• I’m experimenting with new hobbies that I have ZERO interest in turning into my career. The perfect example? I’ve taken up golf. Well, hitting balls at the driving range for now, but maybe one day, I’ll do a full round. Case in point: I’m not going to become a professional golfer anytime soon, so this is purely for fun.

7. Lack of structure sometimes makes me feel “lazy.”

Going back to that whole waking up slow thing? Yeah. I do that most days.

But remember back in the day when I used to wake up at 5 a.m. to bang out blog posts and work on my freelance business?

Now, I wake up around 7 and usually lay in bed until 7:30 a.m. catching up on Twitter or browsing my inbox.

Sometimes, this makes me feel extremely lazy.

However, I try to remind myself that I used to wake up at 5 a.m. because I HAD TO if I wanted to have a blog or grow my freelance business. Because I had to be at work by a certain time, and I had to stay there until eight hours later.

Now, I have ALLLLLLLL day to get things done.

Sounds great in theory, but sometimes those long stretches of open schedule make me feel anxious. I work better under pressure, and better when I know I have somewhere to be or something else to do.

How I’m trying to ease the pain:

• I’m trying to be more gentle on myself. I remind myself that I built my side hustle for four years so that one day I *could* sleep in until 7:30 a.m. on a week day. Guilt-free. My friend and fellow biz owner Caroline recently reminded me: “You didn’t quit your 9-5 to work 24/7.” Touché. 

Finding perspective

At the end of the day, there are downsides to EVERY single job in the world. No career is perfect.

Being an entrepreneur is just a little bit more public, a little bit more coveted and a little bit more glamorized than some other jobs out there.

It’s easy to look at the life of an entrepreneur and wish for what they have — or what you perceive they have.

The grass is ALWAYS greener.

When you choose to become an entrepreneur, you make the choice to embrace it all — the good, the bad and the downright ugly.

This post isn’t meant to discourage in any way — in fact, I hope it inspires you. I hope it makes you think a little bit differently.

If you’re struggling in your career or you’re a business owner feeling anxious and overwhelmed, I hope my honesty shows you that you’re not alone. Not in the slightest bit.

And while today I’m sharing the pitfalls of running a business, I truly am grateful every day for the chance to build and run JL&Co.

The chance to do what I love, on my own terms. (Things that suck, and all).

Fellow business owners — chime in! What do you think sucks about running a business? Be honest!

*Photo via Pixabay

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