by Kristen Miller

Many months before COVID-19 began, I opened the door to a coffee shop and stepped inside. Immediately, I was surrounded.

To the left, a long vinyl banquette was full of coffee-drinkers sitting side-by-side, faces obscured by the screens of open laptops. On the right every seat was spoken for, with even more laptops flipped open and power cords jockeying for space at an overcrowded outlet. In the corner, a jukebox blared out punk music at a volume only acceptable for chainsaws.

I grabbed a tea and headed for a seat hidden behind a row of Insta-worthy foliage. From there, I felt safe to open up my own laptop and get some work done, far from the grinding music and caffeinated gaze of… The young entrepreneurs.

I hid from them because I’m like them, but not one of them. I’m newly an entrepreneur, but I’m not young; my career has already spanned two decades. Most of the people clicking away at keyboards around me were likely attending their first NSYNC concert when I was graduating from law school. And yet here they were, side-hustling and industry-disrupting and doing things I could never have imagined doing when I was their age.

I wondered, how did I even get here? How did I go from working a full-time gig for 20 years to working for myself? And then, of course, I remembered. I’m here because a year ago, I lost my job.

How it Began

At the end of 2018, I was wrapping up a long period of turmoil at work and starting to feel a sense of stability. As my company’s General Counsel, I had shepherded it through some rocky legal woes; gotten through a major leadership transition; completed a Chapter 11 reorganization; and helped to negotiate a successful sale to a larger company. 

But there was one more surprise: our new company announced it would be shifting all administrative positions, including legal work, to its headquarters a thousand miles away. I had two options: try to find a position at the new main office and move, or be laid off. Moving wasn’t in the cards, so after working for three years to save my company from disaster, I found myself out of a job.

I was devastated. Personally and professionally, I felt like a failure—even though the circumstances were out of my control. At first, I didn’t want to leave the house, afraid people I knew might ask me why I wasn’t at work. I had always been a high-achiever, and I expected to do important, impressive things with my life. This did not include losing your job in the middle of your career.

I immediately started applying for jobs, most of which were like the one I had just left—though I knew in my heart that I hadn’t been enjoying my work. I remember filling out applications and allowing the cursor to hover over the “submit” button forever, knowing that I didn’t even want the job to which I was applying. I waited to hear back from potential employers with anxiety and dread, which makes it all the better, I suppose, that I didn’t hear back from many of them.

While in hindsight I’m glad I didn’t go right out and tie myself to some new job that felt as bad as the old one, my self-esteem was taking a beating. I couldn’t figure out why I wasn’t getting any responses; what I was doing that was so wrong, or even worse, what was so wrong with me? So I went to see a career counselor. I handed over my resume for her to tweak and we brainstormed about how I could network with my contacts. In the midst of all this, she asked me to take the Myers-Briggs Strong Interest Inventory and the Predictive Index, just to see if we were on the right path.

Meet the New Me—Same as the Old Me?

When the results came back, I wasn’t particularly surprised. Nowhere did they indicate that my ideal career was “corporate attorney.” Instead, they pointed me to jobs that were creative and involved teamwork. At the top of the list: writing and communications—my college major and the work I had done when I started my career.

For the first time, I had evidence supporting the nagging doubts I’d been ignoring for so long. I can’t explain why I had always tried to run away from the work I was best-suited for, but I couldn’t deny it any longer. We agreed it was time for me to change course and start looking for jobs in communications and public relations.

In the meantime, I was making small talk at a wedding shower one afternoon when the question I’d been dreading came up from one of the other guests: So, what do you do? Tired of hiding, I explained my situation. To my surprise, she replied that someone with my background should consider doing consulting work.

I wasn’t prepared for that response. It sounded intriguing, but way beyond my comfort zone. I’m a Gen X kid—we’re OK not sticking with the same employer for 30 years, but starting your own business was typically not in the conversation. You went to college, got a good job with a decent company, and worked your way up the ladder.

But truthfully, I was envious of the millennials I read about who decided to chuck the whole corporate bit and do their own thing. I knew that wasn’t necessarily happening by choice; between the 2008 recession and corporate cost-cutting measures that gave rise to the gig economy, many younger workers were just doing what they had to do. But the notion of being responsible for your own destiny seemed fulfilling—it was just something I never thought I could do.

Months later, I was strolling around a neighborhood festival when I ran into two young women passing out information about their co-working space. I hesitantly made my way over to talk to them, as if maybe by just being near them I could channel some of their confidence. I told them I had recently considered starting my own consulting business (an overstatement, to say the least), and they were immediately encouraging. Talking to them about their work and the numerous side gigs they were juggling made me feel empowered and excited, but as soon as I walked away, I suddenly felt crushingly ashamed. They’re more confident than you are, I said to myself. You could never be like them. They’ve put themselves on the line to do what they love, and you’ll probably end up crawling back to the comfort of a regular job you hate.

I never wanted to feel like that again.

11:30

As the days without me being gainfully employed stretched on, I finally started to come out of the haze I’d been in since the professional rug was pulled out from under me months earlier. One can only wallow so much, and I was hitting my limit. I stopped caring what others thought about my employment situation, and I started talking about it to friends and colleagues. Surprisingly, some of them asked for my help on a few freelance projects.

I eagerly accepted. I was excited to have something to focus my skills on again, and the work gave me a little confidence just when I needed it most. It also got me thinking again about what it might be like to go out on my own. I decided to dip my toes in the water by defining exactly what I wanted to do and putting it on paper, and checking out an office in that co-working space that caused me so much angst before. But even these initial steps couldn’t convince me to pull the trigger.

I was caught in that over-analysis spin Tina Fey describes in her book Bossypants. As head writer for Saturday Night Live, Fey and her team spent hours writing and rewriting skits for each show—yet she always obsessed at the last minute, continually suggesting changes in order to make each sketch perfect. As showtime approached one week, SNL creator Lorne Michaels pulled her aside and said, “The show doesn’t go on because it’s ready; it goes on because it’s 11:30.” Sometimes you need a hard deadline to realize that waiting on things to fall perfectly into place actually means you don’t get anything accomplished.

When the representative from the co-working space emailed to tell me the office I’d looked at had been reserved by someone else, my clock finally hit 11:30. I could keep waiting for all the variables to be perfect, or I could actually go do the damn thing.

Armed with self-esteem that came and went like free WiFi paired with my husband’s sage advice (“Well, you can’t really make any less money than you are now, right?”), I decided to make the leap. I started off slowly, changing my LinkedIn profile to show that I was now a consultant and explaining my services. I ordered business cards—just 100 of them, so as not to seem too cocky. I started telling a few people I trusted about my new endeavor, and when none of them laughed in my face, I got the courage to tell a few more people. I set up meetings to pitch my idea to colleagues whose opinions I trusted—and those meetings turned into introductions to new contacts who gave me their advice, as well. Then, I marched into that co-working space and rented myself an office. Now I have a desk and a chair and an Insta-worthy plant in the corner.

Lots of the time I’m scared to death, full stop. No uplifting qualifier, like “I’m scared, but so exhilarated…” Starting this chapter is just plain scary. If there is a but, it’s only this: but I’m going to try. Because at the end of the day, not trying would be the biggest failure of all.

And finding the confidence to believe in myself is still a work in progress, but you know what? I think it’s just about 11:30 on that, too. 

Kristen is a management, legal, communications and public relations consultant for Well-Red Consulting and Creative, her new main hustle after several unfulfilling years as an attorney. A native of Louisville, KY, she owns way too many Kentucky Derby hats for someone who is super-allergic to horses. She is an anxious traveler, a bourbon lover, a college sports fan and a music snob. Check out her random musings on Instagram at @kmillerwku.