6 questions to ask before you quit🚪
↩️UNFOLLOW University — June 16, 2023
Happy Friday!
Last year, almost 48 million Americans left their jobs as the Great Resignation continued reshaping how, where, and why we work together. When the pandemic forced us to live in dramatically different ways, it also freed us to examine our priorities.
I was not immune. I knew I would never go back to working the way I did before. But I also had no clue what was ahead when I resigned from my job in 2021.
As isolating as it felt at the time, my experience was not unique. Research suggests that while the reasons for quitting vary greatly, they point to two global trends:
People are quitting entire industries, not just jobs.
We aren’t seeking different positions, we are becoming different people.
At the senior leadership level, it’s still taboo to talk about leaving a job. We’re expected to maintain decorum and protect the perception of being in control. But this “career camouflage” limits our ability to learn from one another and it hinders our view of what healthy quitting looks like.
Quitting gets a bad rap in a country obsessed with extreme success and grit. Socially, quitting means you’re weak, incapable or even undesirable. We’re more afraid of looking like a quitter than being one.
When I resigned, the response was overwhelmingly positive. Since then, I’ve mentored and walked with many professionals through the transition process. So many of us are in a similar season of change but very few of us talk about the pain of change.
Quitting is often a gift, not a glitch. It’s time we understand the difference between quitting and losing so we can safely navigate the distance between endings and beginnings.
🤯 Radical Truth
Quitting is a normal part of being alive, not a forbidden part of being employed.
The possibility of regret has left us organizationally compliant and individually confused. In my case, I realized the work I wanted to do was no longer compatible with the job I was paid to do. The painful process of decoupling my role from my work felt like surgically separating conjoined twins. It was hurtful but not harmful.
So how do you save yourself and your sanity without making the biggest mistake of your career?
You choose a better fight. You embrace the ugly process of letting go of the immediate to prioritize the important. You give yourself permission to leave the known and walk on unproven paths.
Inspired by the book Necessary Endings by Dr. Henry Cloud, here are 6 clarifying questions to ask before you quit your job.
1. What am I (really) afraid of?
Normalize endings. Quitting, leaving or de-committing should be a typical part of being alive, not a terrifying part of being employed. I had to realize - and remind myself - I am so much more than what I do to make money.
Quitting didn't make me a quitter. It meant I could start something new. Fear uses phantom expectations from invisible people to distract you from what you were made to do.
2. In light of my desired future, how will this decision impact me in 10 years?
Treat seasons and cycles differently. Seasons are times of temporary pain on the path to growth, maturity and acceleration. Cycles are patterns of repeated problems left unsolved that have a habit of following us from role to role, like a loyal Labrador.
A few years ago I made a major financial mistake that required both CEO and CFO intervention. It was awful. I wanted to quit for weeks. Instead, my ego became an endangered species and I partnered with my peers to fix it, unintentionally building the very bridges I would need when I was promoted one year later. Fear boomerangs until you catch it, kill it and move on.
3. Exactly how much would it take to do something new?
Count the cost. Income matters most in your prime years when it's a need instead of a want. So the idea of a career pause or pivot becomes a financial decision versus a freedom one.
After months of planning, praying and calculating, I decided the pain of regret would be worse than the pain of failure. My angelic wife, Alisha, and I sat down and created a budget based on my being a bum for 12 months with minimal income. Luckily, 10 years ago we started living on 50% of our income so we wouldn't get landlocked into an "executive lifestyle" that actually limited our financial flexibility. Am I earning what I made 2 years ago? Nope. Am I measurably better in every area of life? Yes.
I love this thinking from Rishad Tobaccowala: "So many people price themselves out of their dreams and fail to recognize that Plan B was the real plan." Fear feeds on ambiguity and hates specificity. Build the budget already.
4. What options am I ignoring because they seem unsafe or unsmart?
Choose your choices. We all seek proven, high-traffic pathways with maximum visibility and minimum uncertainty. Don't ignore your desire for safety and predictability, rather, define what’s behind it.
Smart leaders choose from their available options: go, stay or delay. But strong leaders know the options you can't see are only hidden because you haven't found them yet.
I wasn't brave enough to walk away from the pay, prestige and certainty of a gig like Patrón so I found another one. Yep, I accepted an amazing CMO role in the health tech space, intent on building one more business, brand & team before I was ready to walk away.
I thought I was being smart by choosing from what I could see but sometimes you have to walk in the dark for what you want. Fear forces you to move the finish line back so you're never ready to end the rat race that’s already over.
5. How will I feel one year from now if things stay the same?
Let go of hope. Hopelessness can be helpful when we acknowledge that more time, effort or energy won't change anything or anyone. I had to discern the difference between "giving up effort" and "giving up commitment."
This mindset allowed me to de-commit from one version of the future as a tech CMO while focusing on a new, somewhat foggy future where I'm mentoring, writing and learning new skills. As Dr. Henry Cloud asserts: "Failing well means ending something that is not working and choosing to do something else better." Fear hopes for comfort but it comes at the price of progress.
6. What work am I built for?
Do work worth doing. Falling in love with your work often leads to falling out of love with a job. Your work (which I'll briefly define as your purpose or passion) is why you're here. Work helps you live a life while jobs help you build a career.
Jobs are bricks. Work is the building. Titles, roles and awards look good on a resume but good work leaves a legacy that won't fit on paper. The entire article is worth reading but certainly allow these words from Gianpiero Petriglieri to throat-punch your brain: "I don’t think it’s worth loving a job, or an organization. Let me repeat it: they will not love you back. But if a job, or an organization, helps you find work and people worth loving, then it has been good, and it is worth honoring, both while you are there and after you are gone." Fear would rather audition for someone else's part than work for the role you are made for.
Do you need a book or a blog post to be brave? Not at all. But other people's experiences help pressure test your own intuition so you can do the improbable: be honest with yourself.
Necessary Endings was a book that helped me clarify my own convictions and push through the loneliness of leaving.
Quitters aren’t losers.
Leaving isn’t the end.
Giving up hope can be helpful.
Fail well.
⚡️Courageous Question
Knowing what I know, would I reapply for the job I have now?
🗣 Wonderful Words
"I don’t think it’s worth loving a job... they will not love you back. But if a job [...] helps you find work and people worth loving, then it has been good, and it is worth honoring."
🙏🏽 Prayer Package
God, when tough places turn dark, you have always been my guide. During times of uncertainty about the way I should go, help me stay still and lean into you. You are always here - listening, loving and talking. Take away the noise of other people’s expectations. Clear out the confusion that comes from my appetite for control, safety and failure-proof living. Empower me to let go of what’s never been mine so I can grab hold of the peace you promised. Your power is so much bigger than my decisions so I give this to you. Amen.
🎵 Wherever I Go - Lexi 📡
🛠 Practical Tool
Read this article on building “Success That Last” by Laura Nash and Howard Stevenson. Creating a Personal Kaleidoscope can be an extremely clarifying step in diagnosing precisely what you’re missing, measuring and solving for before you accept a new role.
This 20-minute exercise is a research-based start to considering how achievement, happiness, significance and legacy all play a role in the work we’re designed to do.
To the leader thinking about leaving, I’ve been there.
You're tired. The exhaustion is real and your patience is at an all-time low, which means the risk of making a mistake is high.
It’s hard. The job, the team, the board, the group, the church, the people all need you. And so do you. Tribes are built on trust and you've been the glue so long it's hard to imagine things working without you.
But before you decide to leave, dedicate time to (re)learning what’s really going on inside your head - and in your heart.
The real reason you won't leave is fear. Fear is a shadow of something meaningful and tangible. It means you actually care. While it's impossible to be 100% fearless you can fear less by choosing to face it.
Conformity and "success" - however you define it - rarely stay married for long. Since most of us don't have the benefit of stunt doubles I hope my failures & reflections can help you rehearse for what's next at work.
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Every Friday I’ll send you 5 courageous ideas to help you redesign your work life by making better career decisions:
🤯 Radical Truth - A story from me
⚡️ Courageous Question - A challenge for you
🗣 Wonderful Words - A quote worth remembering
🙏🏽 Prayer Package - A moment of meditation
🛠 Practical Tool - An actionable resource
