To The Leader Thinking About Leaving

Why We Really Resist Walking Away From Jobs and People

To the leader thinking about leaving.

Don't. Not until you admit why you're worried or why the thought of staying makes you miserable.

You're tired. The exhaustion is real and your energy is at an all-time low, which means the risk of making a mistake is high. But the job, the team, the board, the group, the church and the family 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 the crew without you.

I know because I am you. After 7+ years I left my role as the Global VP of Marketing at Patrón Tequila last week to spend one year writing, advising and publishing. The response was overwhelming. After 1+ million views, 800 comments and countless messages, I realize many of us are in a similar season of positive change but very few of us talk about the pain.

Why? Most days, I'd rather be an expert sharing tips than a survivor showing wounds. But timely evidence beats old advice any day. Instead of waiting one year to tie a ribbon around my past-tense learnings, I hope it's more useful to show you where I'm at today, scabs and all.

So how do you save yourself and your sanity without letting someone down? You don't. You choose a better fear. You embrace the ugly process of letting go of the immediate to prioritize the ultimate. 

Here are a few reflections from Necessary Endings by Dr. Henry Cloud, a book that helped me clarify my own convictions and push through the loneliness of leaving.

1. Normalize Endings

Q: What are you really afraid of? Really.

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 others to distract you from what you were made to do.

2. Treat Seasons and Cycles Differently

Q: In light of your desired future, how will this decision impact you in 10 years?

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.

Fear boomerangs until you catch it, kill it and move on.

3. Count the Cost

Q: Exactly how much would it take to walk away or do something new?

Income matters most when it's a need instead of a want. So most responsible adults consider a career pause as part of retirement. I guess I needed an early dress rehearsal. 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 me 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. 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.

4. Choose Your Choices

Q: What options are you ignoring because they seem unsafe or unsmart?

Don't ignore your instincts, test them. Smart leaders choose from their available options: go, stay or delay. They seek proven, high-traffic pathways with maximum visibility and minimum uncertainty. But strong leaders know the options you can't see are only hidden because you haven't found them yet. Honestly, 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 & experience 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 so you're never ready to choose yourself.

Fear forces you to move the finish line so you're never ready to choose yourself.

5. Let Go of Hope

Q: How will you feel one year from now if things stay the same?

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. The Work Worth Doing

Q: What work am I built for?

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 highest vocation, calling, purpose, passion) is why you're here. Jobs help you build a career. Work helps you live a life. Jobs are bricks. Work is the freakin'​ Taj Mahal. Titles, roles and awards look good on a resume but 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 it was made for.

"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."​

- Gianpiero Petriglieri 

Do you need a book or a blog post to be brave? Nope. But, if you're like me, other people's experiences help pressure test your intuition in a mental laboratory where you can do what seems so hard: be honest with yourself.

The real reason you won't leave is fear. Fear is fake. It's a shadow of something meaningful and tangible but it doesn't exist outside of our emotions. While it's impossible to be 100% fearless you can fear less by choosing to face it. Safety and "success"​ - however you define it - are very distant cousins that only meet in movies. 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.

Lastly, I'm a big fan of frameworks and tools. I'd love to share some "job decision"​ templates, candidate tools and resources I've used over the years to make better, braver decisions on entering, exiting and finding roles worth doing. Drop me a comment with requests and feedback, and I'll start sharing on my blog, podcast and on LinkedIn.

Thanks to everyone for the encouragement and wisdom while I'm under construction. It means so much!