Redefining what a successful career looks like by asking who I want to become as well as what I want to achieve
My youngest daughter behind the wheel of her own old-timey car when she was four years old.
When I was around five years old, I was behind the wheel of a car for the first time. To be clear, it was Mr. Toad’s Wild Ride at Disneyland, where I steered an old-timey car through the twists and turns of an imaginary world. I truly felt that I was in control of this tiny vehicle. I turned left, turned right; I took my responsibility very seriously.
It wasn’t until a few years later when I got back on the ride that I realized the steering wheel doesn’t actually determine where I want to go! I could turn left or right or spin the wheel in a circle and not crash. I was never in charge; the car was on a track.
I think about that ride a lot when I think about my career. How often am I making a choice about where I want to go? Am I actually steering my career, or am I on a track that culture’s expectations have already laid out for me? And if I am stuck on a track, how can I break free from it?
Taking My Own Interest Seriously
My first experience jumping the track was my senior year in college. I just took a course that opened my eyes to climate change. I wanted to figure out how and where I could make a positive impact with my job, even when people around me weren’t convinced sustainability could be a reliable career. The adults in my life would look at me with the ‘I used to be passionate about things too, don’t worry, you’ll grow out of it’ look, waiting for this environmentalist phase to run its course. Even my career counselor laughed at me. He said, "Dallase, I thought you said you need to make money," insinuating that to make a positive impact, I would have to forgo financial security.
I was worried. When I talked about wanting to work in sustainability, I felt a little like that five-year-old behind the wheel. My parents had known all along that I wasn’t actually steering the car, even as they smiled at how seriously I took it. Now I wondered whether the adults around me saw my career ambitions the same way: sure, let her think she can change the world. Sooner or later, she’ll realize she’s on a track, too. What worried me was that they might be right.
I felt like I needed to jump the track. So I joined the Peace Corps. It was an early decision to pull myself away from cultural expectations, take my own interests seriously, and see where they could lead. In many ways, it worked. I came back with a growing interest in the environmental field and went to grad school to support my passion.
But choosing my direction once didn’t mean I stopped finding myself on someone else’s track.
Looking Beyond the Accomplishments
Fast forward 12 years, I get invited to attend a week-long Sustainability Leadership Program at Harvard. I was established in a career in sustainability, and I was a new mom, just past that first year of parenthood. I remember dropping my daughter off at daycare and walking over to spend the day surrounded by people doing really impactful and impressive work. (Side note: They all could pay their bills. Take that, career counselor!)
These were people contributing to the kind of change I cared about. I wanted to understand how they had built their careers. And because I was so fresh into parenting, I also wanted to know how the rest of their lives worked.
So when there was time for questions, I asked some of the keynote speakers: Do you have kids? How do you manage it? What does that look like in your family?
All of the speakers described arrangements in which their spouses took on most of the childcare and responsibilities at home. They described it as an intentional division of labor and responsibilities that allowed them to focus deeply on their careers.
I appreciated their honesty. And I also found their answers challenging.
I wanted to make a meaningful contribution through my work. I also wanted to be very present in my daughter’s life. Was I going to have to choose? Was the career I admired built around an arrangement I didn’t want for myself?
I remember talking through this with someone at my table, a person who became a friend of mine. He said, “Well, Dallase, maybe your contribution in the field is being an example of someone doing important work while intentionally making room for the family life you want. It’s going to look different. But perhaps you could help show what that difference might look like.”
That conversation helped me jump a track.
I had been looking at one part of someone’s life and imagining it as a roadmap for my own. I could see their professional accomplishments. But until I asked the question, I couldn’t see the choices and support behind them, or what those choices made room for elsewhere in their lives.
People get to prioritize different things. I wanted to be intentional about what my priorities would be.
Making My Intentions Count
When I started Trust, I wanted those intentions to show up in how I ran the business. I knew they had to be integrated into my work. So, my annual goals for Trust always include being present for my family.
Typically, my projects have deadlines and people waiting on something I’ve promised. However, my kids don’t have a written contract and a scope of work to hold me accountable. I take my client commitments seriously, and I wanted to give my family commitments that same attention.
So I made time codes for tracking when I want to be present with my kids— chaperoning school trips, volunteering, and attending their spring and fall concerts.
Those were things I want to account for when I look at how the business was doing. Am I doing meaningful work? Is the business financially healthy? Am I making time for my family and myself, fostering these important relationships and taking care of my health?
Having these measures in place hasn’t stopped me from getting drawn toward other people’s goals, but it has helped me recognize when it’s happening.
For example, just last year, someone reached out to see if I wanted to join a small entrepreneur cohort in Boston that was connected to a larger global organization. I was curious, so I took a call.
I learned from their website that the cohort had a revenue threshold for membership. Trust met it. But almost immediately, I started wondering: What if I have a year when I take on less work? Should I start taking on more projects? Would I say yes to work I didn’t really want? I started to feel overwhelmed. The pressure felt real. I hadn’t even joined, and I was already mentally rearranging my business to meet their requirements.
During my informational interview, they talked about being able to help me build a million-dollar organization. I asked what other indicators of success they used for the cohort. Social impact? Health and well-being? What else would tell us that the business was doing well?
They couldn’t point me to a clear answer beyond the financial measures.
I realize that the panic I felt told me something was wrong with this approach. Of course I want to make good financial decisions and I want to pay people well, but what if making as much money as possible wasn’t my main goal? I felt like I broke the system when I asked this question. Although it was tempting, I realized that wasn’t a track I wanted to be on.
Choosing My Own Measures of Success
We can spend an entire career optimizing our lives for performance indicators that we never consciously selected. Salary, revenue, job titles, promotions. They are measurable, so they’re easy to track. But to attain them, we often have to put aside the “unmeasureable extras:” relationships, health, reliability, presence, integrity.
Conventional career planning (as I learned early on) focuses on getting a job with a good salary so one day we can retire and finally live the life we really wanted, filled with meaningful relationships, great friendships, physical health, and mental freedom. I realized I don’t have to wait until retirement. I also realized, you have to cultivate all of those things before you retire.
Being intentional about being reliable, respectful, and present at work and at home felt like an embarrassingly unambitious career goal. Being home for dinner, doing craft projects with my kids, being a good friend, finding time each day for myself. But the more I pursue them, the more radically ambitious they seem. Keeping the balance of work, life, family, and personal development is no joke!
My schedule is packed with all the things—including meetings, facilitating retreats, volunteering at my kids’ school, going to the doctor, running, and more. Everything goes into one calendar because it all is in pursuit of the same goal: becoming the person I want to be. By that metric, a 10 am meeting with a client is just as important as my scheduled quiet time away from all screens. I am breaking down the walls between Work Dallase and Mom Dallase and Friend Dallase, allowing them to have a shared set of values. Increasingly, I am less interested in asking whether Professional Dallase is succeeding and more interested in whether I am showing up as myself across my entire life.
