Finding Purpose in the Past
In knowledge careers with no clear path, going forward means digging deep.
For most freelancers, solopreneurs, and coaches I’ve met, ‘career moves’ don’t feel like forward progress. They feel good but aimless.
That’s because more often than not, promotion-hunting and status-seeking are an exercise in buying time. Like a sailor adrift, we’re fighting to stay afloat until, by inspiration or chance, we stumble onto security, purpose, and meaning.
For knowledge workers and others, the path is clouded and the destination unsure, but we do have some hints as to where the road may end.
Mining the Past
Philosophers debated for centuries whether our character is fixed at birth — nature or nature — but if you’re reading this, there’s one thing for certain:
You’re not a blank slate now.
Your innate traits, environment, and experiences have worked together for years to construct the current-you, and your experience is a hidden cache of clues about what future-you will enjoy, excel at, and find meaning in. Although this seems obvious, we rarely think to look into that cache for valid reasons:
We don’t remember past events well. Instead, we reconstruct memories over time, so we don’t trust them. Since our feelings about the past are often clouded by societal expectations of how we should feel about them, we sometimes just see more of the same stuck-ness in our memory. And to top it all off, the past is — by definition — not timely. It was a different us, a different time, a different situation, so we assume it doesn’t apply.
All together, trying to get useful facts from reflection can be like trying to tell how bright the sun is by staring straight at it.
Which is why we approach the question indirectly, looking for clues to our authentic selves that get around the noise.
An entire industry of personality tests has arisen to try and solve this problem, inventing tools like the Myers-Briggs Type Indicator. Unfortunately, most are inconsistent, poor predictors, lack strong scientific validation, and are superficial enough that we’re already aware of what they have to tell us. They can still be useful for starting conversation and self-reflection, but they’re more like Harry Potter houses than honed instruments.
Instead, I’ve gained the most benefit from asking indirect but specific questions:
- What did I spend most of my time either paying money or doing for free?
- What specific event left me incredibly excited or satisfied? What was I doing and who was with me?
- What specific event did I loathe?
- What hard evidence do I have of how my family, friends, coworkers, and clients perceived me?
- What did I think I’d be doing when I grew up?
- What skills, hobbies, and passions, did I enjoy for at least a year?
- What communities have I been a part of?
These help get around the problem of digging around and coming up blank by bringing up the context of specific events along with authentic signals of interest and passion. I may be embarrassed by my old fanfiction, but I can’t deny how much time I spent on it.
Even a casual reflection can be surprisingly useful. As long as something satisfied you and didn’t hurt anyone, it suggests future actions likely to do the same.
If you want to be systematic about it, break your life into phases that mark turning points in your self-identity. Although these are usually marked by milestone moments — graduation, quitting an addiction, marriage, first child, a new job, entry into a community — they don’t have to be.
Once you’ve broken down these plot twists in your life story, give each one a box on a page — or several pages — and ask the above questions of each phase of your life. Put the boxes side by side so you can compare answers over time, and then reflect. If you struggle with the exercise, try visualizing a younger version of you and asking them the question — you may be surprised by what you find.
I started using this approach myself in 2016 when I left the active-duty Navy after 7 years as an officer to start coaching full time.
I had no idea what I should pursue next and felt I was starting entirely from scratch as my previous jumble of a journey seemed more random than useful.
As a youth, I was a serial hobbyist, taking on a sport or passion for two to three years before moving onto another: fencing, piano, Tae Kwon Do, soccer, jiu-jitsu, gymnastics, whatever seemed interesting. At 16, I thought I’d be an English teacher. After four years at the Naval Academy, I served as a navigator, an anti-submarine officer, and as support staff with a SEAL Team. I was a swing dancer, a GRT, a glee clubber, and took on fitness challenges from mountain ruck races to powerlifting. Besides a penchant for physical activity, nothing screamed ‘coach.’
But on deeper reflection through this exercise, there was a clear thread working through all of it.
I remembered being 14 years old and spending countless hours debating on Theology Online, scribbling stories, and writing ‘topical essays’ that no one would ever read. Thankfully, no record of these remains. At the Naval Academy, I led physical readiness preparation, helping struggling students in my company pass their physical exams. As a junior officer in the Navy, I headed study sessions and made study guides for qualification exams in my spare time. As a dancer, I’d volunteer to help demonstrate and assistant-teach new students as part of our motley crew.
Through all of it, I loved the thrill of movement, the challenge of breaking down and expressing ideas, and the joy of watching the ‘aha’ moment someone learned a new skill or realized they were capable of more than they thought possible. Not only did my past passions serve me as a coach, but they also guided what kind of coach I wanted to be.
I had the opportunity to manage and own a gym — it would have been forward progress by some definitions — but it wouldn’t be going forward along my path. On the other hand, when I was offered a position as a teacher — then director — of a school for new coaches, the choice was obvious.
What kind of content to focus on, what certifications to seek, which people I most wanted to serve — all these nebulous questions became a lot clearer.
The Path is Yours
The riskiest part of this kind of assessment is that it brings no guarantees. Knowing that a previous ‘you’ would hate a new job or promotion is small comfort when that job offers a bigger paycheck or a clear status signal.
It usually doesn’t take long before our clever brains hide the key from us and trick us into following the familiar route.
But if you take a look back and trust what you find, you may find your path forward isn’t quite as clouded as it seems.