How to Career Coach Yourself
Small Notebooks, Big Feelings, and Radical Honesty
It was a sunny and cold February Minnesota morning: brisk with a tease of warmth. I got out of my car, wrapped my coat tighter around me, and walked into the Anoka-Hennepin District Headquarters where I would be starting work writing a Math Textbook. I checked in at the front desk and waited in the lobby. I questioned whether dressing in business casual was the right move here. Or even if it mattered. In Grad School they told me to dress business casual when teaching but that never fully made sense to me. I mean Mrs. Frizzle is arguably one of the most famous teachers and her fits were wild (and fantastic). Teachers care for kids, we’re not in a board room - calm down everyone.
Anyways, they eventually called me back to the meeting room and I walked in to fresh pastries and free coffee (a luxury I had never gotten as a teacher - the best we ever got was three large dominos pizza’s during teacher appreciation week in the staff lounge filled with old sad saggy couches).
“I could get used to this” I thought. “The people are nice, I get pastries and coffee, not a bad life.”
Unfortunately (and expectedly) though, wining and dining me with coffee, great people, and pastries wouldn’t be enough to keep me in the Education world…
After leaving teaching, I had a professor who had kept in touch with me and heard I needed some work, and so he helped get me a job writing a Math textbook. So in January of 2014 I found myself on a team of 10 or so, all charming and winsome retired teachers over the age of 50. And then there was me - a still idealistic yet burned out 24 year old. I got paired with a delightful older woman named Deloris who had trouble using a computer sometimes. She was my absolute favorite.
Now, while this was the best paying job I had ever had, there was an expiration date on it. It was a contract gig for like 8 months or something like that (could have been shorter or longer I am notoriously terrible at remembering how long a period of my life was).
I also knew textbook writing wouldn’t be my gig forever. And also: textbook writing was a slippery slope to standardized test writing (which would have been like me leaving the Dark Side of the Force but then becoming Darth Vader suddenly). I was already getting offers for that. *Darth Vader Heavy Breathing*
Now, before I can go forward and tell a newer story, I have to go back and tell an older story (as all good stories are want to be told). One thing I didn’t tell you about when I left teaching is how I decided I was going to leave teaching
The Small Notebook Experiment
I only learned and am learning recently (at 36 years of age) how to engage with my emotions in more healthy ways. That’s a nice way of saying, “for most of my life I ignored my emotions, pretended I didn’t have them, stuffed them down, shamed and belittled them, etc.” Super rare for a man to deal with emotions like that I know (*sarcasm*). So when I was teaching, I wasn’t listening to myself. Wasn’t listening to my body, my feelings, nothing. Just working and grinding away doing what I thought was best.
But, my own mental health started to get pretty dark. I was sad and very depressed. But I didn’t want to be a quitter. And especially - this happens in teaching and service jobs a lot - if I quit, I was having a hard time not feeling like I was letting down a bunch of kids I really cared about. (Is this good-hearted-ness a tool sometimes used by people in power to keep people in service-esque jobs and also maintain shit conditions? Maybe...)
So what did I do…? Why an experiment of course! (Yes I’m aware I did an experiment on myself to avoid just listening to my gut, feelings, and reality-before-me… lol + smh).
Every day after work, I kept a small notebook in my car (Silver 2007 Toyota Corolla - her name was Emma and she was a quiet country girl who was skeptical of my motorcycle named Sapphire - and yes all my cars/vehicles have names and backstories). In that notebook I had written 20 positive emotions and 20 negative emotions with space next to each. And every day after work for 60 days, I sat in my car and put a tally-mark / check next to the emotions I felt.
My plan was after 60 days, I would listen to / do whatever had more emotions (stay or go / positive or negative). Now, let’s be clear - I should have known after 1 week. I should have known / listened to myself right away. But did I do that? No. And collecting data is fun so I was distracting myself. Obviously.
So after 60 days the results and data were in and it was… (to no one’s surprise) overwhelmingly negative. The data was there. And so the decision had been made “for me”. As my friend James Olivia would probably say, “you weren’t ready to take responsibility for yourself and the experience you wanted to have so you found some ‘objective’ external to ‘make the decision for you’.” Ouch. But also very much not wrong.
Career Coaching Myself
Now, during this time, I was trying to help myself a bit. I got into career coaching but like… for me. I career coached myself for 2 years. I studied career coaching, read every book, interviewed career coaches, and then developed my own curriculum for myself (that I’ve since used very effectively on other CEO’s, Leaders, and Job Seekers in the world).
One of the things I’m best at in the world is filtering through nonsense to find the best strategy to use. The two books I landed on as the best of the best for career coaching are (1) What Color Is Your Parachute (WCIYP) - the Workbook (not the book - I still have no idea what a parachute or color of a parachute has to do with anything lol) and (2) Designing Your Life (DYL). I call WCIYP the “what” book and the DYL the “how” book. (more on all this all some other time).
But what’s often hardest about career coaching (I found with myself and find when working with others) - is that it requires an integrated level of honesty with ourselves that we rarely… have. Because when I did the WCIPY workbook - I did not like the answers. I was in a teaching profession at the time - and all my natural enjoyments and gifts and skills were in math and problem solving and system building. But I wanted to help people directly and work with people. But I loved doing Math and building systems that scaled. But I wanted to help people. But it burned me out. All the “but’s”.
The WCIYP workbook basically was like, “none of how you’re wired shows that you’ll be a happy sustainable teacher”. Oof.
This was one of the first and largest times I ran into the paradigm of “I want X” versus “I want to want X.” Subtle difference, but massive implications when acknowledged and honored. And it’s something I still see often whenever I do career coaching for others.
One other thing I learned about myself is a concept I call “Time Horizon of Impact or Effect”. The question to ask yourself is, “What kind of results do I need? And on what time horizon?” For example, teachers work for 5, 10, or 20+ years and rarely “see the effects” of their care and work. It’s an investment in a generation of people. You don’t see people change or grow quickly. Maybe when you’re 60 you’ll get a letter from a former student that shows the impact you had. Maybe.
Or even being a therapist, you work with a client from months, weeks, or even years before you might see growth or change. And this is why it’s so important to (1) enjoy the actual daily work you do (one of the core principles of WCIYP) and (2) be honest with yourself about the results you need to / are wired to see and pursue.
For me, I realized I need to see results quickly. And often. (Hence why I eventually loved landing in Software, Data Engineering, Data Science, and Finance.) I like working on a problem, solving it, seeing results, and moving on. It took me a bit to be honest about that because it felt like a weak thing to admit (especially as a teacher at the time), but it’s true. So the long time horizon of impact that teaching brings was never going to be along term fit for who I am and what I want in the world.
In summary, I was trying to make 1 + 1 = 3. And the “math wasn’t mathing” (as the kids say). I had over-idealized who I was and what I was capable of (sustainably). Given what I also had learned about reform in the education system, I was also not thrilled at the chances of being able to have an effect at changing the system.
So I walked into the Principal’s Office - and told her I was leaving and I couldn’t do it anymore. Mid year. Which is one of the shittiest things you can do as a teacher to both the students and your fellow staff. But I couldn’t hang anymore. And I also knew now more broadly it wasn’t where I was going to go with my life.
So I left and implemented (maybe for the first time?) a phrase I have now for myself and others,
“An ugly step towards health is often better than standing perfectly still in whatever un-health you may find yourself in.”
Honoring that is both ugly/shitty and positive. Holding the nuance and seeming-binaries together.
Beginning Again
And so that’s how I left and ended up writing a Math Textbook with Deloris. For an 8 month contract. Unsure what the shit I should do next or what kind of career would work for me.
And in that bit of desperation, and reflecting on the WCIYP work I had done - it was then that I remembered that I really enjoyed a coding class I took in High School. Now, “coding” is a generous term here. It was a Web Dev class working with HTML and CSS. No Javascript. No actual server-side or database or stats languages. Nothing. But I remember liking it and being good at it and it just kind of made sense to me. (Also I remember just getting done with all the work quickly, playing a very pixelated Runescape, and then using a text-to-speech translator + an internet digital phone call service to order our classroom pizza on multiple occasions 😏😂. Giving me too much free time and a computer lab has only ever resulted in automated nonsense and fun for everyone.)
So while working writing the Math Textbook, I decided I would take a few night classes at Minneapolis Community and Technical College with the goal of just learning some software programming languages and seeing if I liked it.
And I did like it. A lot.
And I was good at it. Very good.
So at 25 years old, with the textbook writing contract ending, I went back to Community College to learn as many programming languages as I could and change careers.
To be continued…
Resources Mentioned
James-Olivia Chu Hillman - *chef’s kiss* of a brilliant thinker on relating, relationships, and so much more.
What Color Is Your Parachute - the workbook (not the book). I often in career coaching refer to this as the “what” book (helps you narrow down What you want to do).
Designing Your Life. I refer to this as the “how” book - which helps give you a paradigm of how to approach a career shift (small experiments + slow gradual freighter-ship changes versus giant speed-boat-esque turns).
Thanks for reading. Wishing you all the good things today.
Matt Rowe