I Left Corporate America to Be My Own Boss—Then Went Back 2.5 Years Later


You could say I stumbled into entrepreneurship. Back in 2012, I started a blog to document, for my own accountability, how I was stretching my savings during a career transition. To my surprise, the blog gained traction quickly, which helped me land a content and social media job.

Soon, big brands, like Prudential and TurboTax, started noticing me and paying to advertise on my site. This revelation, that companies would pay for my influence, was a complete gamechanger. I began daydreaming about the “digital nomad” lifestyle so many other bloggers and entrepreneurs glamorize on Instagram. Maybe I could do that, too, I thought.

Over the next two and a half years, I’d book thousands in ad revenue, grow my readership to 80,000 each month, pick up freelance writing clients and consistently bank $4,000 to $5,000 a month on top of my full-time salary.

I was ready to be my own boss. Nevermind that I didn’t have more than $3,000 saved or a real plan for how I’d run my own business.

The Other Side of Solopreneurship

It didn’t take long to realize that the romanticized version of running my own business didn’t exactly mirror real life. While I did manage to outearn my full-time income by $6,000 the first year, that wasn’t much more than I’d made doing it on the side the year before. And it didn’t go nearly as far after accounting for health insurance premiums and self-employment taxes. Plus, I was spending a lot of time chasing down clients for money owed.

I also wasn’t prepared for how the boundaries of my work and personal life would bleed together, and how lonely I’d feel at home all day by myself. And as someone who loves to be organized, the free structure of the day overwhelmed me.

For year two, I shifted my business model away from intensive writing projects and toward winning more advertising clients, thinking that’d give me a break from my invoice collections role, but this was a mistake. I failed to plan for how some site upgrades would increase my expenses and affect my bottom line—and I ended up taking home even less each month.

Not only did I feel financially strapped, but I fell victim to the comparison game. Working for myself wasn’t the flexible, carefree life I thought other bloggers in my community were experiencing so effortlessly. This exacerbated issues with depression I’ve had since college, to the point where I became unproductive, which further tanked my earnings. Maybe I wasn’t cut out for entrepreneurship after all.

Work for Yourself or for Someone Else? 

What I learned the hard way is that the entrepreneurial life isn’t for everyone. Starting a business—even a small one—takes a lot of time, money and hustling. And while the flexibility can be great, it can also be lonely and exhausting work. While some thrive on their own, others (like me) crave company. 

It’s easy to romanticize working for yourself, but there are benefits to working full-time for a company, too, like hanging out with co-workers, getting paid on a regular schedule and having someone else cover most of your health insurance premiums and even match retirement contributions.

In 2017, I decided to go back, taking a full-time content manager position. Surprisingly, the transition was pretty painless, and I haven’t regretted the move.

Working from home in my pajamas was great, but it’s a lot like ice cream for me: Eat too much, and you’ll get sick (and slow and unproductive). Toward the end of my time on my own, I found myself binging out on the couch almost daily in front of Netflix. That might sound ridiculous, but it’s easy to slip down that rabbit hole when you’re working alone and feeling unmotivated. An office environment provided the social interaction I needed, too. I’d really missed creative collaboration.

I also didn’t give up blogging just because I went back to a company. Instead, I run the blog on top of my 9-to-5. By doing both, I anticipate I’ll make more than triple this year what I made at my low point as a solopreneur.

Best of all, looking at the blog as side income, rather than my livelihood, gives me the freedom to enjoy it again. Before, I had to focus so much on running a successful business—and, you know, feeding myself—that I missed out on the creative outlet. Now, I write when I’m inspired and am able to pick and choose my projects. That’s the dream I was chasing after the whole time.