Two Years In

What did you want to be when you grew up?

When I was small I wanted to be a golfing farmer. Then I wanted to be an artist. Then I wanted to be a writer. Of course, nobody took the first one seriously, but pursuing a career in a creative field was strongly discouraged. "There's no money in creative pursuits" I was told, over and over again.

So imagine my surprise when I found myself sitting on the Roost rooftop patio a few weeks ago celebrating my second anniversary as a full-time business owner.

Not only do I get to do the creative work that I love to do (writing) every day, but I get to leverage the thing I love to do another thing that I love (helping people) while building the life that I want for myself. That's pretty incredible.

So with that revelation in mind, I wanted to touch on a few things that I've been reflecting on over the past few days as I ponder what got me here, and how things have changed in these past two years:


Outgrowing Corporate Life

The advice I got the most often when I was growing up was "find a job and keep your head down" which - in case you haven't met me - is the polar opposite of who I am as a person.

I'm not a lady who keeps her head down and her mouth shut, and it always proved challenging in work environments where I didn't have the control or opportunities to experiment, try new things, and get creative with problem-solving.

For a long time I thought it was character flaws that were keeping me from being a happy employee. Why couldn't I just fit in? Why did I have to challenge my supervisors when I thought I knew of a better way to do something? Why did I continue to lose motivation after the first few months of doing the same tasks day in and day out?

Mostly I wondered: why did everyone else not seem to have these same challenges?

It was crazy-making, and it wasn't until I started freelancing in 2014 that I started to experience the kind of control and freedom that I'd been looking for and failing to find in my corporate life.

I realized that the problem wasn't me, it was the work I was doing and the places I was doing it.

Let me be clear: there's nothing wrong with a corporate job if that's what you want, but for some of us it feels like trying to fit a square peg into a round hole every day.

It's nice to not feel that way anymore.

Finding Amazing Opportunities

The one thing that I don't think I was prepared for was the amount of opportunities that being a business owner afforded me, and how much those experiences have enriched my life.

I used to wile away my days at my desk, watching people on Twitter share talks and presentations and workshops and all these fun and exciting-looking opportunities. I wanted to be doing those things, but I didn't know how to get there.

Here's the thing about being a business owner, though: in order for your business to be successful you have to put yourself out there.

This is where that whole "being unable to keep my head down / mouth shut" aspect of my personality really acts as a blessing: I'm comfortable putting myself out there and getting up in front of people, so I'm comfortable with the hustle associated with promoting and building a business.

These days I write articles, run workshops, speak at conferences, and I even have my own print column. While, yes, I could have certainly leveraged my personal brand to find these opportunities, having a business gets me in front of other professionals in a way that being an employee at someone else's company didn't afford me. And honestly? That's probably the coolest part.

Learning to Manage Others

In 2016 my business grew enough that I began working with outside contractors to help manage my workload. By the time I rebranded and launched Starling Social earlier this year I'd already been working with contractors for a while, but formally announcing that we have a team felt like a huge accomplishment. Looking at our About Us page and seeing more faces than just my own is still a bit mind-blowing, and I'm so thankful to work with the passionate and dedicated people that I do.

On one hand, having someone help you manage your workload is a huge boon. On the other hand, sharing my thoughts and developing the processes needed to effectively on-board others was scary. My anxieties make me afraid of failure and "being wrong" and it was intimidating to open my business up to other people and let them in.

That being said, being forced to take a long, critical look at how and why I did things helped me gain a much deeper understanding of the value of using the right tools, processes, and documentation to run my business and serve our clients.

They say the best way to understand something is to teach it to someone else, and that applies in business, too.

Gaining Confidence

The single biggest change in the last two years is the confidence that I've developed as a result of being a business owner.

I can feel it permeating every conversation I have; there's a security, a solidarity in my sense of self that just wasn't there a few years ago. Of course, I still have moments (or days, or sometimes even weeks) of doubt and struggle, but overall working for myself and managing both clients and contractors has helped me grow into a significantly more confident person, both personally and professionally.

I have anxiety, and until recently I was seeing a therapist who was helping me work through some traumatic childhood experiences that contributed to those feelings. While therapy was invaluable (really, I can't recommend it enough if you feel like you need it) it was the daily practice of getting up, working by myself all day and facing my problems and challenges head-on, and reflecting about those challenges in a safe space that really contributed to my increased overall sense of well-being and confidence.

I really do believe that being your own boss is one of the best things you can do to build up your self-confidence. It pushes the boundaries of your comfort zone in so many small ways every day.

Moving Forward

Business is growing and these days it feels like I have more stuff to do than hours in the day, but that's okay. I'm learning to develop and maintain a work/life balance, which can be hard sometimes when your work is the thing you love to do.

I believe that people create their own luck, though to be perfectly honest most of the time it still feels like I stumbled into this amazing, stressful, and challenging opportunity even though I can look back and see the years of work and dedication that it took to get here, even if I didn't know that this was where I was going. And honestly, that's the coolest part: not knowing where this adventure is going to take me.

I'm really excited to see what the next few years bring my way.


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