A Year of Solopreneurin’ It: What I Imagined vs. The Reality

My, how time flies! I almost can’t believe I’ve been solopreneuring it for a year now. I started my company last year because I wanted more flexibility and autonomy over my daily routine. I also wanted to make travel a big part of my life, which is why I went on an adventure once a month for the entire year (fueling the flames for my travel blog, ClairesHoliday.com).

I’ve passed the one-year mark and I’ve learned so much about what it takes to hustle, work with an ever-rotating number of teams and companies, face uncertainty, stress, a daily structure, and sometimes, loneliness.

When I talk to friends and family about my new ventures and work life, they seem to think I’m “free” to do what I want, when I want. While technically, that’s true, I’ve become a lot more strict with my schedule and free time during the week.

It takes a lot of planning and intention to free up some time to go on that hike or take the day off to go to Tahoe (sadly, I only got to board midweek once).

This is what I thought would happen vs. the reality:

What I thought: My new schedule would allow me to stroll in and out of morning yoga classes, run errands, and do whatever I wanted during the day.

In Reality: It takes mad discipline to be on your own (and I have yet to go to a yoga class in the morning)!

When you have your own company, you’re… on your own.

There’s no one to mentor you or hold your hand along the way. Because of this, I made sure to build a solid network of colleagues and new friends. The first year, I never turned away a request to meet someone for coffee or a drink, even if that interaction yielded nothing. I connected with freelancers in my area and attended various meetups and conferences. It was really fun and it gave me the chance to passed out my newly minted business cards.

HustleCon in Oakland, 2017

I thought that having all this freedom to create my perfect work day and try to be more intentional with my schedule would be easy… but it wasn’t. It was really hard to figure out how to structure my days, and I’m a pretty disciplined person to begin with.

I created a schedule for how many hours and days I’d dedicate to which client, which helped ease the sometimes hectic and scatter-brainedness part of juggling so many projects at once.

I also experimented with taking breaks during the day to go for a long walk or maybe even have lunch with a friend.

What I Thought: All I need is a few steady clients and I’m set.

In Reality: Finding a steady client isn’t easy. Clients can let you go, at any time, for any reason. Everything was uncertain and sometimes I just flew by the seat of my pants. 

Hanging at the Bryan Park NYC WeWork for a networking event.

As my own boss, I had to make sure there was a steady rotation of potential clients streaming in. This meant constant meetings, emails, and hopping on calls to learn about new opportunities.

This alone was a big time suck, and more often than not, nothing ever came out of the calls and initial meetings.

This uncertainty caused me a lot of anxiety, but I realized this scarcity mindset was clouding my reality, which was: I always had clients and there was never a shortage of opportunities.

So, I stopped thinking this way. Whatever happens, happens. If I need to fly by the seat of my pants, so be it. Life is an adventure!

What I Thought: Work will have a hard stop at the end of each day.

In Reality: I worked very long days and constantly thought about work. A lot more than when I was a full-time employee.

FinCon in Dallas with Lynnette The Money Coach, Earl, and Stacy.

I recall working full-time and constantly juggling a million things — meetings, emails, project managing; it just seemed never-ending. For some reason, I thought that I’d have more of a “clean break” when consulting. I start a project, finish it, and I’m done, right?

To some extent, yes. But while the project is going on, it’s go, go, go! It was also a lot more intense because I was not physically in the clients’ office either, so I had to make my presence known.

Working weekends and nights became a regular thing.

What I Thought: Having autonomy over my days will be awesome.

In Reality: Having autonomy over my days is awesome. 

This is the main reason why I decided to break out on my own, and I have to admit, the freedom is a huge perk. The funny thing is, I’m super strict on myself when it comes to what I’m allowed to do and not do, probably more than a cool manager would be at a full-time place of employment.

But it’s nice to be able to go to the doctor or tend to an errand in the middle of the day and not have to send emails letting people know where you are or why you’re not being responsive.

Whatever happens next, I’ll be okay with

I think having my own company has helped tremendously in the last year. I learned so much about setting up a business, taxes, and how to handle irregular paychecks. But more importantly, it’s opened me up.

I say yes a lot more often (personally and professionally) and I genuinely enjoy meeting new people and learning about new companies and opportunities — regardless of whether I think they will end up being a client.

If I had to sum it up, being a solopreneur has sparked a curiosity in me that wasn’t previously there. I’m looking forward to seeing what the rest of the year will bring!