How I Decided To Leave My Dream Job
A new series about making big decisions
Hi to the new Practically Deliberate readers here! If you joined based on a recommendation from
or , welcome. I don’t take it for granted that you’ve invited me into your inbox.For readers who aren’t already signed up for The Double Shift and
, you should (do it now, I’ll wait).A quick (re)introduction to myself and this newsletter:
I’m Abby Davisson, a leader, author, and entrepreneur. Throughout my career, I’ve sought out innovative, data-driven ways to combine profit and purpose — first as a leader in organizations focused on making the world better and now as an author and entrepreneur focused on making people’s lives better.
At least twice a month, I share actionable, evidence-based insights on intentionality, decision-making, and personal development (like those in my book, Money and Love: An Intelligent Roadmap for Life’s Biggest Decisions) that lead to greater well-being. Popular posts include:
How Deliberate Rest Can Make You More Creative and Effective (my first post)
I’m excited to share a new series with you today (and a request for your help at the end) — let’s get to it!
Introducing a new series: How I decided to…
When I was in elementary school, I was obsessed with Choose Your Own Adventure books. The ones where you face a choice and then, depending on the path you choose, are sent to a different page. (On p. 4, you learn the castle is guarded by a dragon. Do you try to kill the dragon or do you run away? If you choose to face the dragon, turn to p. 16.)
I was never confident the path I chose was the “best” one, so I stuck post-it notes on the choice pages so I could turn back and follow all the potential paths.
The problem with my approach to Choose Your Own Adventure books is that it didn't actually prepare me for life. Not only is it rare to encounter a dragon in real life, you can’t follow all the potential paths. You choose a path, and your life is shaped by your choices (where do you live? work? do you get married? have kids?). You can certainly change course along the way, but you can’t ever go back in time and choose differently.
My fascination with decision-making led me to write a different kind of book — one with a framework that can be applied to many types of big life decisions. The idea is the framework can be your guide as you face daunting choices. That way, even if the path doesn’t turn out the way you expected, you feel more confident in your approach.
In addition to the framework, two other elements feature prominently in the book: data and stories. Readers have said they especially love hearing how others approached big life decisions, so I decided to introduce more stories in this newsletter.
Big decisions — like leaving a job, getting married, moving, having a kid, getting divorced — are scary, because even when they’re voluntary, they often lead to a period of upheaval and transition.
Some of these transitions are especially destabilizing — they’re what author
calls “lifequakes” in his insightful book Life is in the Transitions: Mastering Change at Any Age.Lifequakes are more common than we think; Feiler’s research shows that “the average person goes through three to five of these destabilizing events in their adult lives,” and the ensuing transitions last five years, on average.1
For the “How I decided to…” series, I’ll feature stories of how people approached a big decision, pulling back the curtain on their thought process behind the scenes.
My intention is to help you feel less alone and offer helpful tools and insights for when you face similar, lifequake-inducing decisions.
Because I believe in role modeling, I’ll share my own story first.
How I decided to leave my dream job
This month marks two years since I gave notice at what was once my dream job: leading the corporate foundation and social impact arm of a Fortune 200 company.
Since then, I’ve been asked how I made that decision more times than I can count. In a pinch me moment, I was even asked by The Wall Street Journal.
Many people, especially middle managers, are contemplating leaving their jobs — jobs that they, too, likely once loved.
By sharing my story, I hope to offer useful guidance, reassurance, and inspiration. And if you read until the end, I have something even more concrete to offer...
The truth is, I’m my own guinea pig — I used the strategic decision-making framework in our book (we call it the 5Cs) to make this big decision. Below, I’ll highlight three Cs that had the most impact for me in this particular decision: CLARIFY, COMMUNICATE, and CONSEQUENCES.
A series of clarifying moments
The first step in the framework is to CLARIFY what’s most important to you. It’s a crucial step — but it’s often the hardest, since we’re powerfully influenced by other people’s wants.
I was hired at Gap Inc. when I was 38 weeks pregnant [note to hiring managers: if you want a loyal employee, hire someone about to become a parent] and started when my baby was four months old. I was exhausted by all the learning curves I was climbing at work and at home, but I loved working for a global brand, making a difference, and learning from amazing colleagues.
Over the next seven years, I experienced several life transitions. I had another child. My parents moved into a retirement community nearby, with my father in independent living and my mother in skilled nursing (she needed significant help due to a serious accident years before).
As I sorted through my mom's belongings, I reflected on her tremendous legacy and what I wanted my own legacy to be. And something inside me shifted. But I wasn’t ready to leave yet.
In fact, I had just launched the company’s first employee resource group for working parents, and I and my co-founder had committed to a two-year term.
I began collaborating on a book with my professor-turned-co-author while working full-time. A few months after we started working on our book proposal, the world shut down, and my kids (then ages seven and four) started zooming into “school” from our dining room.
For more than two years, the book was my passion project — something I did on nights, weekends, and occasional days off.
Because I was working non-stop, I didn’t have much time to pick my head up. But there were a few moments I couldn’t help but pay attention to:
I heard a talk in which the speaker drew a distinction between your job (what you get paid to do) and your work (your purpose or calling). On a piece of paper, I drew a Venn diagram and listed what I got paid to do vs. what I felt called to do. At that point, I realized there was very little overlap — I changed, my role changed, the company changed, and the world changed.2
At a routine dermatologist appointment, I had a suspicious mole removed. While I was waiting for the biopsy report, I thought about my mom, who had recently passed away. Facing mortality — hers and now potentially mine — provided a sense of urgency.
A recruiter reached out to me about a similar position in another (bigger, growing) company. Intrigued, I had additional conversations. I made it to a final interview with the hiring manager — and didn’t get the job. Instead of feeling disappointed, I was relieved. I live in my head a lot, so this experience offered a useful way to check in with my intuition about what I wanted (for more insight into your decision-making style, take this quiz).
A wise friend asked me when was the last time I had a good day at work. It took me far too long to answer — a telling sign.
Sometimes there’s not one moment that prompts a decision — sometimes it’s a slow build, a series of moments all pointing to the fact that something needs to change.
It was also growing clear that while it was possible to write a book while working full-time, it wouldn’t be possible for me to promote a book while working full-time (especially for my then-boss — who was my fourth in fourteen months). A choice was looming.
There’s research on regret that says our most enduring regrets are actions we don’t take that would bring us closer to our ideal versions of ourselves.3
My ideal self is a creative, entrepreneurial person who takes calculated risks — but I had been playing it safe, staying at the same company for more than nine years.
My efforts to CLARIFY helped me see that there would need to be “an evolution to my revolution” for me to live in alignment with my ideal self.4
Conversations and checking assumptions
No one makes decisions in a vacuum, especially when you’re in a long-term relationship. So the second “C” in our framework is to COMMUNICATE with those most affected by the decision.
Ross and talked a lot about what work we wanted to do next, mostly on the regular weekend hikes we went on as a family during this time. Our kids would run ahead, giving us a rare opportunity to talk uninterrupted. Being in nature — outside the chaos of our everyday lives — helped us think more expansively.
During the early pandemic, we’d explored moving to a bigger house in the suburbs (who didn’t want more space?). Ultimately, we decided to stay put for several reasons, including to retain career flexibility. A bigger house would have meant a bigger mortgage, tethering us to our corporate jobs — but we both had entrepreneurial aspirations.5
At that point, Ross had left his job as CFO at a fintech company and was playing a Lead Dad role. He was being recruited for other CFO jobs…but wasn’t feeling excited about any of them.
I was the sole breadwinner and the one whose health insurance plan we were all on. Instead of sharing kid responsibilities as we once did, Ross was shouldering most of them (leading a team spanning from India to San Francisco meant it was not uncommon for me to be on Zooms from 7 am to 6 pm).
While I appreciated that he was picking up the lion’s share of parenting while I worked and wrote, I felt disconnected from my kids, and I didn’t like it.
Rather than another CFO job, Ross wanted to start his own investment firm. He’d worked in a similar field earlier in his career, and he wanted to try doing it his way.
While I was all for that, I assumed I’d need to continue working in a “W2 job” with benefits. I told him I was worried I’d resent him following his dreams while I deferred mine. Neither of us wanted that to happen — but we were both concerned about the financial consequences.
We talked to a financial advisor, who ultimately wasn’t very helpful. However, the conversation motivated us to dig deeper into our finances to see if we could make simultaneous (vs. sequential) entrepreneurship work.
We investigated the cost of health insurance. We looked at our budget and our balance sheet. Thanks to our habits of consistently saving and investing, we found we had some financial runway.
To be clear, we also had a great deal of privilege — including a lack of educational debt, thanks in large part to our parents. That fact is certainly not lost on me. However, in addition to that privilege, our ability to have transparent conversations about money and career ambitions proved invaluable.
Prototypes and experiments
The final step in our framework is to consider the likely CONSEQUENCES, both in the short-term and long-term.
There are numerous ways to approach this step. I’m a big fan of prototypes and experiments as ways to test hypotheses; they help approximate the consequences of making a change without actually making one.
As Dorie Clark notes in a recent HBR article, it’s helpful to find small ways to validate big moves before jumping in with both feet.
As I contemplated a career pivot, I tried to get exposure to the things I wanted more of in my work:
I sought out speaking opportunities and learned about getting paid speaking engagements.
I continued writing the book, which confirmed how much I enjoyed non-fiction writing (board memos didn’t count).6
At the behest of Stanford Business School’s career center, Myra and I prototyped a live, cohort-based course grounded in our research and decision-making framework and offered it virtually to Stanford Business School alumni. It got rave reviews, and I loved the experience of teaching it.
All of these experiments validated what my Sparketype assessment had told me years before: I’m a Maven/Sage, and I feel most alive when I’m learning things and sharing them with others by speaking, writing, and teaching.
I certainly could have done more. For example, I could have talked to entrepreneurs who were bootstrapping their own companies to better understand the challenges they faced (vs. the venture-funded entrepreneurs I studied in business school).
But I had already done a lot of homework. There were diminishing returns to additional research. I was beyond exhausted from working, writing, and parenting — all during a global pandemic; I couldn’t continue to do all the things. Something needed to change.
The analogy I use is that I had to let go of one trapeze in order to catch the next one.
And so I set a date in March (after year-end bonuses were distributed) and gave two months’ notice.
Two months is a long time, but I’ve always believed in the importance of “sticking the landing” and not burning bridges on your way out the door.
Ultimately, this allowed me to set my team — people whom I cared (and still care!) about deeply — up for success after I left.
And relatively speaking, after spending several years considering the decision, two months wasn’t that long.
Candidly, I don’t know how the current adventure I’ve chosen will turn out. But because of the approach I used, I feel confident in my decision in spite of this uncertainty.
Know someone whose big decision I should feature in the “How I Decided to…” series? Reply to this email or let me know in the comments!
Abby’s Latest
In this section, I usually recommend a beloved product that checks all the boxes for me. But instead of chocolate or socks, I’m sharing something exciting coming later this spring.
I mentioned that two years ago, my co-author and I taught a live, cohort-based course to Stanford Business School alumni on navigating big life decisions.
At the time, our book wasn’t out and we were still road-testing our material. Yet we received glowing feedback from participants:
“This class was extraordinary in unsticking the inconvenient questions we rarely want to ask ourselves, let alone spend time or resources answering…I made incredible progress in the iterative work of clarifying what I truly want…”
“This class was positively provocative!”
“The sessions were a great time to slow down and think through big decisions in my personal life. Having a framework is incredibly valuable for this exercise.”
Over the past two years, I’ve continued to research the topic of making big life decisions; write about it; and (as you’ve learned in this post), I’ve also lived it.
I’m considering teaching the course again — only instead of offering it exclusively to Stanford alums, I’d open it up to anyone ambitious about their career and personal life who’s feeling daunted by a big life decision. If this is you, I’d love for you to join!
You’ll apply a trusted, evidence-based framework to a complex choice; identify the common pitfalls that lead to regret; and build confidence in your decision-making process.
Can you fill out a short survey to help me design the course? As a token of thanks, you’ll receive enrollment priority (the course will likely be capped) as well as a discount. Thank you in advance!
Please also share this with anyone who might find this post (and course) useful!
Deliberately yours,
Abby
H/T to Ed Batista for reminding me that the world changed a lot during this time.
The original research paper is also an interesting (albeit denser) read.
H/T to Kisha Modica who introduced me to this phrase when I shared I was leaving.
This article helped us feel better about that decision.
To be clear, writing a book isn’t a “small experiment,” but I’d already jumped into that with both feet!
So excited for your course! What a great opportunity
This is really reflective and lovely, Abby! I feel like as an academic, there are fewer choices (there are never more than 3-4 jobs listed a year, you take which one you can get) so it does simplify things.