Parachutes

Unpacking the courage to leave my 20-year career

One early Saturday morning in June 2020, I drove an hour north of my house to do something scary.

After watching the instructional video, strapping on my harness, and waiting around the hangar for ages, I finally saw my name appear on the screen. I boarded the small plane with my instructor. I felt peace on the flight, despite looking out the open hatch and knowing I was about to trust my life to a piece of fabric. It was time. We waddled over to the door and let gravity pull us out into the sky. The view was beautiful, the jump was exhilarating, and the dopamine high coursed through my body for hours.

Peering down on fields from the North Texas sky, about to leap

Three weeks later, I submitted the paperwork to take early retirement.

The decision to leave my 20-year airline career had been brewing for a while. Last week, I wrote about cancer, the first catalyst to change my relationship with work. The next catalyst unfolded in three parts.

Part 1: Growing Discontent

Post-cancer treatment in 2014, I transitioned from a high-stress operational leadership role to create my dream job at the same company. Together with one of my favorite coworkers, we created our department’s first analytics team. Initially a team of two, we had the opportunity to develop new technical skills, learn new tools, and focus on deep thinking and research.

We slowly grew the team, recruiting a mix of the best talent in other areas of our department and a recent college graduate. The department was high functioning and low drama. Other department managers regularly told me what a joy it was to work with each person on my team.

Over the next couple of years, I reluctantly took on more responsibility as other department leaders left. I spent the majority of my work day shuffling between three buildings to attend meetings. In Fall 2019, a departmental re-org took away the team I’d built and left me without an explanation. I struggled to find meaning in my work, and my frustration began to seep out through my face.

My coworker snapped this photo in a meeting. OVER. IT.

Part 2: A Devastating Loss

By the beginning of 2020, I made peace with my diminished role. I intended to leave the company in a couple of years when I was eligible to retire with lifetime flight benefits. I wanted a second career with greater social impact, and this was a nudge to push me towards that. I dipped my toes into external learning when I enrolled in Seth Godin’s altMBA workshop.

The month-long leadership workshop started in January 2020. It included around 20-30 weekly hours of reading, group sessions, and project work. I attended while working full time. I felt invigorated to learn and interact professionally with people from all over the world in a variety of professions. Previous to the altMBA, my professional network was almost entirely in aviation and at my airline. This was my first online cohort-based course, and the first time I’d used Zoom.

Two weeks into the course, I got a call that a dear friend, a coworker and former mentor, died.

My friend worked overtime in a high-stress job at my company for over 30 years to reach his dream of retiring in California. He retired less than two years prior, and moved to California a year later. He was a cancer survivor, and died of organ failure following a flu-like illness.

Friday AM-one week after he died

I woke up to a flurry of texts revealing more heartbreaking details about the situation, and it was clear his surviving loved ones needed some assistance. I had about an hour of work I needed to do to wrap up our big 10-week planning event at the office, one of the most important functions of my job. When finished with that, I could do one small thing to help, which was ordering some urgently needed items to be delivered to his family.

I and around 75 other people waited over 45 minutes for the leaders to arrive to wrap up the planning session. The leaders nitpicked the plan over minutiae, everyone was wasting time, and my stress kept building. What was supposed to be done at 10:30am was not complete nearly 90 minutes later, and multiple items remained on the agenda.

My impatience grew. Someone commented I was being “spicy”. I felt torn from responsibility pulling me from both sides, and I realized I had chosen the sequence incorrectly.

I approached the facilitator of the meeting, and I said “let’s get it moving, cut out the ceremony, make a decision, and move on. I have something grave to deal with personally and I need to leave.” We wrapped it up in record time. I then completed the task I needed to help my friend’s family.

Same Friday, PM

I’d already planned to take the afternoon off for an altMBA coaching session and some other tasks. I left my cubicle in the windowless basement and drove in the beautiful sunlight to my boyfriend’s apartment for a quick lunch before the call. I walked in the door and melted into tears. I’d held it together all day and could no longer do so. He comforted and fed me.

I composed myself for the coaching session. I knew the sessions were fairly open-ended but did not know exactly what to expect. I mainly sought insight into how I can keep the momentum of the altMBA going and work towards my goal of a more meaningful career.

The coaches asked questions about what I wanted to do, and I gave somewhat open answers. They kept asking me to dig, which felt impossible. I said I really didn’t have a clear picture of what I wanted, so one of the coaches asked me to say what this future in two years feels like. Here were her notes from my ramblings:

feels like freedom

time outside

time in nature

having people listening

agency over time, location and people that I spend my time with

being able to stop things that harm people

help people learn how to find better ways

And then one of the coaches said:

I think you know what you want, but you are hiding.

I did not feel ready to hear this, and it stung. I teared up a little, tried to hide it, and a few minutes later wrapped up the call. How am I this far into my life and still unclear about what I want?

I went to lay down on the bed and sobbed. My brain was done.

Saturday AM

The next morning I read online the first parts of Tim Ferriss’s Four-Hour Work Week, one of the books on my post-altMBA “to read” list. This list of questions punched me in the face:

1. How has being “realistic” or “responsible” kept you from the life you want?

2. How has doing what you “should” resulted in subpar experiences or regret for not having done something else?

3. Look at what you’re currently doing and ask yourself, “What would happen if I did the opposite of the people around me? What will I sacrifice if I continue on this track for 5, 10, or 20 years?”

I selected my college because I had a full scholarship and didn’t want debt or help from my parents. I worked part-time throughout college and high school so again I could have full financial freedom. I had worked in a corporate job for the previous 20 years to build financial security. I had taken few risks.

The story I told myself is that I was doing all of these things for freedom, but had they actually given me freedom? Being realistic and responsible has given me freedom from debt. I had many things in my life for which I was grateful, but I hadn’t allowed myself the space I was craving.

In two years, I would have the time to fly anywhere I want in the world as long as the flights have an open seat. What would I do with that? I was afraid of what would come with freedom, because then it’s all up to me.

I didn’t want to end up like my friend, toiling for years and only having a taste of freedom at the end. With my history of cancer, my life expectancy is below average. I had to start building this into my life sooner.

Part 3: The Parachute

My friend’s celebration of life was February 29, 2020. I didn’t know this would be my last large social gathering for over a year.

About a week later, we started making pandemic contingency plans at work. We were quickly in crisis mode, figuring out ways to draw down flying, work remotely, save jobs, and ultimately protect our employees. The next two months, I did some of the most intense and meaningful work of my career.

We were doing real work again.

Offering voluntary early retirement packages, or “buyouts”, was one of the efforts to save jobs. I eagerly awaited the buyout details, disappointed to learn they didn’t include lifetime flight benefits for me. The rest of the package was generous, though. Those like me who had been at the company for over ten years could leave with a year’s salary and benefits. That parachute could stretch for at least two years—giving me freedom two years earlier than I’d planned.

I was invigorated by work for the first time in years. I knew it was risky to quit my job during a global pandemic with high unemployment. I felt guilty leaving my coworkers during this time of crisis.

I wanted to do it anyway.

On that day in June 2020, I decided to physically embody the change I was contemplating. I jumped out of the small airplane with an experienced jumper and a parachute on my back. Three weeks later, I signed the paperwork to leap from my 20-year airline career into an unknown future.

No one warned me how skydiving weirdly stretches your face

Next week: my first week of freedom and the ritual I created to disconnect from my corporate identity