Where do you see yourself in five years?

A 5-minute read that covers 5 years of my life.

My Dad taught me my first “grown-up joke”. It was “How do you make God laugh?” and the response is “Tell Him your plans for the next five years.”

Subtle humor based on a life lesson about disappointment is not the normal kind of thing to send a fifth grader into fits. When I understood it (with amusement rather than laughter), I knew that for the rest of my life when things didn’t go as planned, a part of me would always think “I just made God laugh”. With no embarrassment, I can say that the five years from Spring 2019 to 2024 have been my best run of jokes for God. Um…Winning?

At the start of 2019, my plans were primarily career-focused. My personal life was good. There was no real drama coming from friends or family, and my life in San Francisco was great. I had no idea that 2019 was setting me up to do four of the Five Most Stressful Things a person can do, all in 2020. We didn’t have a child, but the rest? Death of someone close, Check. Job change, Check. Marriage or divorce, Check (although delayed by COVID). Moving, Check (and bought a house). That wasn’t just laughter. That was pointing and laughing.

Early in 2019, my C-level changed. I had joined Kevin’s IT Leadership team in 2016 and about a year in, we had a solid plan to transform Core Services. About halfway over that arc, I was getting a new boss. Kal’s arrival shook things up but I’m an optimist and saw the opportunity. Within months though, it was clear we had different ideas about my business line’s value. My plans were to start 2020 by trying to change his mind, while grudgingly doing a job search on the side. That made God laugh. For Thanksgiving’19, we took my mother to meet the soon-to-be in-laws. A week later, her health took a turn and I started 2020 in Norfolk, providing primary care, then hospice support.

Before any of us knew what COVID was, kidney disease took my Mom. On March 10, I spoke at her funeral. On March 14, I flew home for some rest before starting on her estate. On March 17, San Francisco went into lockdown. My plans were to recover before tackling things in Virginia and starting a job search. That made God laugh. Instead of rest, that March I kicked off months of workdays that started at 5:30am and regularly went past 7:00pm.

In July 2020, I flew back to Virginia for the first of many work weeks shutting down my family home. In September, Billy and I spent a weekend in Palm Springs evaluating neighborhoods and choosing between recommended realtors, but with no intention of buying yet. My plans were to sell Mom’s house before taking on another mortgage. That made God laugh. We bought a house that weekend, and cut our trip short. We would ride out COVID lockdowns working in separate home offices, with a pool as a bonus.

In November, I shared that news with my boss and team. We put off discussing a return to the office, since that topic was unclear for everyone, and Billy and I had many friends who lived two city lives. My plans were to rent in San Francisco and do the same. That made God laugh. The week of Christmas, just days after I drove our moving truck south, Kal added a Principal Architect role to my nearly complete department reorganization plan. He wanted my name in that block. Refusing, in order to remain as Director, came with challenges that would likely mean leaving Patelco by summer 2021.

I did agree with Kal that I was wearing two hats and not delivering fully on either. Viewed objectively, a professional expert role without the trappings of people management might have been a better fit, but I didn’t want to exit Leadership. In hindsight, I think I accepted the change because I was burned out and didn’t have the strength to fight it, but also because in my heart I knew my boss didn’t have the coaching skills and we didn’t have the relationship that would make it possible for me to make the changes he needed me to make.

No matter how the new job played out, the Bay Area lost some of its pull, if I had no future in Patelco Leadership. Still, I was determined to give it my best shot. My plans were to focus on projects, without the demands of department administration. That made God laugh. With no clear plan for transition of my responsibilities and a new Director with no experience in credit unions, I continued wearing both hats but now without authority. Within months, my challenges worsened as the folks who for years had been my primary business partners, simply stopped taking my calls or accepting my meetings.

Then, in June 2021, our CEO took five minutes on our All Team call to celebrate the prior weekend’s Technology accomplishment. She publicly praised another leader for the result of five years of my work. I have never felt as unappreciated or undervalued. After the call, I told Billy my last day would be December 15. I gave notice on December 1, and exited with an email to much of the organization thanking them and saying goodbye. Having resolved Mom’s estate, I went on sabbatical. My plans were to take time for myself and find something new in a year or so. That made God laugh.

Sabbaticals are not common in the US, especially in Financial Services, so I really didn’t know what to expect. Getting back the sixty hours each week that had been going to work, however, meant I felt better almost immediately. It took months for real recovery to begin, but by summer the world was reopening and I felt great. My plans were to have a normal summer and rejoin the world. That made God laugh. My recovery to that point was entirely physical. My heart was still broken and my mind was still overly anxious. I had made no progress unwinding the prior three years, and worse, I couldn’t see how badly it was affecting those around me.

At the start of my sabbatical, I had intended to expand my support network, probably in the summer, to approach my return to work methodically. I followed through on that by finding a Leadership Coach and a Career Coach, and revisiting my goals in therapy. The conversations followed the same basic theme: what future did I want, how could they help, and what goals should we set. Unaware I hadn’t made any real recovery, I happily defined a future to move towards. I then went about blindly bringing to my personal life the same Big Goals and lack of healthy boundaries that repeatedly defined my relationship to work. Fortunately for me, my emotional gas tank was still empty so when I tried to run at full speed, I fell flat on my face almost immediately.

At a conference that July, I shared with some peers what I was doing with my coaches. I said I’d learned “the things I always thought were my strengths can’t help me anymore, and what I thought of as my weaknesses are what I need to lean into”. The people in that circle physically leaned into the conversation. The engagement was awesome. Then, only a few hours later, in response to some question, I devolved into a word salad of poorly regulated thought and exhaustion. It scared me to experience such extremes in human interaction, especially on the familiar subjects of my career. I had to admit I was not ready for prime time.

Applying new knowledge, I did NOT respond by ignoring the stumble and carrying on. Instead, I paired back my goals and redefined success. I paused the work with my Leadership Coach (but walked away with an amazing reading list). I worked with my therapist to rethink what we were trying to do. I recommitted to the work with my Career Coach, but we relaxed the timeline. The scaling back worked, and over the rest of 2022 I made real progress on healing. I began 2023 physically healthy, and spiritually ready to try again. My plans were to do a conventional job search and get back to work. That made God laugh. For the first half of the year, I struggled with rejection and silence. Since I was intentionally reaching outside the restrictive credit union space, nobody seemed interested.

In summer 2023, I changed tactics to lean into my roots. I expanded my searches to capture more credit union (and industry adjacent) roles. Immediately, I got responses. While “you were our #2 choice” is the closest I’ve come to starting a new job, I’ve had some amazing interactions. I’ve even maintained connections with some leaders who hired other candidates. I’m doing monthly calls with my coaches, and have reconnected with my old mentees. It feels like progress at the right speed, even if I’d like to go faster.

There are jokes written about the natural rivalry between Tech/Geeks and Sales/Marketing. My career places me squarely in the Tech/Geeks category so building and promoting myself as a brand is outside my comfort zone. Unfortunately, the traditional “update your resume and submit it for job postings” thing doesn’t seem to work anymore. So, I’ve started publishing more of what I write and this year will be selling the Russ Brand (not affiliated with stuffed animals). My plans are to make God laugh and I think I have a shot.