Why I took a job (after being a business owner for 14 years)

Image courtesy of Renée Hendricksen

Image courtesy of Renée Hendricksen

Change is funny — once you make one, others often come tumbling after.

A little more than a year ago I found myself creatively bored and in need of a change. After much deep thought, I pivoted Bet On Yourself to focus solely on technical experts. They’d actually been my primary clients anyway — I just made it official and stopped taking work outside the tech industry. The transition was smooth and easy.

I thought I was done with change.

Then I went to Ruby Conf where I met up with an industry acquaintance. That conversation led to helping a tech company create career maps for their team. Then I started doing executive coaching with some of their leaders. Eventually it led to a conversation I didn’t expect. I was talking with the CEO, Renée Hendricksen

“I really enjoy working with you. We make good partners.” I said.

“I agree. Want to be my COO?” She replied.

“Ha ha ha ha.” I laughed before pausing.

"Wait. Are you serious?” I asked.

“Yep. Think about it.” She replied. 

And so I did. I thought of nothing else the entire weekend. At first I thought the idea was just silly. “Me? Take a job?” Through my work and writing for Fast Company, I had a reputation as a business owner who was determined to stay independent. I didn’t start my career trying to start a business or stay independent. I was having a hard time finding a role that challenged me and suited my skills. So I stayed independent and figured I’d never take a traditional job again. It wasn’t something I ever considered. After 14 years on my own, I thought the “having a job" part of my professional life was done.

I couldn’t imagine a job that would meet my unique constellation of talents and experience, and have a culture that matched my own values. But something gnawed at me. I kept thinking about. By Sunday I broke down in tears. I realized that I’d abandoned my dreams of doing this kind of work during the last recession when jobs in the field dried up and never returned. While it fulfilling to teach tech companies and devpreneurs how to market themselves to build a sustainable business, the truth was that I’d been longing to do even more organizational strategy work and to have a bigger impact.

The role entailed organizational strategy helping the company go from a scrappy startup to a sustainable business. The role was one part organizational strategy, one part change management and internal communication, and one part people work. It wasn’t a dream job, I don’t believe in them, but it was perfect for my skillset, experience and the kind of work I’d been drawn to throughout my career. By working inside of a company, I’d be able to have a bigger impact than the work I was doing for Bet On Your People as an outside consultant.

To add to the job responsibilities, I’d already been working with folks across the company for months and loved working with each of them. The final thing that made the job so irresistible was the relationship I had with the CEO. It was one of the best partnerships I’ve had in my career. Though I was skeptical of having a “boss” again, Renée was someone I could imagine working with well. After talking with a few close friends and trusted family members, I told Renée I was willing to be considered.

In May I joined Travis CI as their Chief Organization Officer. Yes, you read that right — it’s not a typo. Don’t worry if you’re unfamiliar with that title. We made it up. The traditional COO title didn’t seem to fit what I was doing, so we created one that fit the role perfectly. We came to love the title because of it’s focus on organization, a nod to the to my area of expertise: organizational development. My field is quite niche and not always well understood so there isn’t a well articulated career path or opportunities to do this work. When I tell people my expertise they’ve often never heard of it before.

Often people think it’s the same as HR (aka People) work. While both work at the intersection between individuals and companies, the work they do is actually quite different. Part of what excited me about the role is that Travis CI is such a forward thinking company that understands that organization development (OD) isn’t the same as HR (aka People) work. Hiring an executive position that focuses on organizational strategy and effectiveness is rare.

Having an opportunity to have this kind of impact using my expertise was one I couldn’t pass up.

Two months into the job, I’m thrilled with the choice I made. I’m proud to work for a tech company that recognizes the need for organizational strategy, not just HR. Everyday comes with new creative challenges that excite me. I spend my days thinking about how to maximize collaboration, how to communicate changes, building manager onboarding programs, and coaching people on StrengthsFinder so they can be their best. The team is bright, dedicated and passionate. I feel honored, valued and creatively fulfilled. I have zero regrets about taking this job.

Considering a job after being independent?

Listen for the cues

Sometimes you think you’re heading one direction and then life heads you in a completely different one. Don’t panic. Take the time to think about what you really want. The things we desire don’t always show up in the packages we think they will. Slow down to ask yourself the deeper questions. Listen to what your intuition says even if what it’s telling you is a complete surprise.

Find the right fit

Flexibility is one of the most often mentioned reasons for independents to go out on their own. It’s a huge benefit, especially if you’ve worked with rigid schedules or had to be in an office for many years. In the past, I’d worried that taking a job might feel like chaining myself to a desk, losing the flexibility I treasured as an independent. This didn’t turn out to be true. The company I work for is a distributed team so I don’t have to go into an office. This made the transition easier.

I don’t fret about less flexibility, in part because my company has a minimum vacation policy. Rather than what I was used to in American companies, I found a company which values giving its team time away to regenerate. This means I still get to travel and plenty of time to take care of everyday life events. When you’re looking at taking a job, looking at the company culture, and how they live their values is essential, especially for folks who are used to creating a work culture of their own. No matter how good the job or the steady pay might be, don’t neglect company culture. If it doesn’t match your own, you won’t be happy or successful.

Prepare for the change

While interviewing I reduced my other commitments so that I had time to prepare myself for my new job. Borrowing from my chef friends, I took the practice of mise en place  (https://en.wikipedia.org/wiki/Mise_en_place) to my life — a form of change management. To ensure a smooth transition, I spend several weeks focusing on putting everything into place in my life. I decluttered my house, took care of lingering errands, and made plans with friends I hadn’t seen in a while. I also talked with my partner about the changes we need to make in how we divided our household tasks. He stepped up to take on additional tasks while for others like cleaning, we decided to outsource. This turned out to be one of the most important things we did — when the demands of my job ratcheted up, we were prepared. Though I feared the transition would be hard on our relationship, we sailed through it with ease — I credit the mise en place planning for a large part of this.

Don’t worry about what others think

Working for yourself means you have to create a brand and that often becomes your identity. For a long time I was known for being independent. Letting go of this identity was a slow burn for me — nearly a year from when I made the change in my business to taking a job. Even though I knew it was time to let go of the “Independent Business Owner” identity, it was hard when others seemed to have a hard time of changing the way they saw me. Their questions made me wonder if I was making a mistake. In the final weeks while I was considering taking a job, I decided to stop talking to others about it completely except for a few trusted folks I knew would support me no matter what. It was lonely not sharing what was going on but ultimately it allowed me to make the right choice for me with confidence.

I don’t know if I’ll have a traditional job for the rest of my career or go back to working for myself. I do know that I’m done making hard and fast rules about how my career should proceed. There are so many ways to have fulfilling work — a linear stepladder-like career is no longer necessary. Find the next rung on the ladder that works for you and sometimes, you might even just find a whole different ladder.

Wondering whether you should become a leader or stay more technical? Curious about working for yourself? Check out our ORIENT Program.