Meet a Backslider: Interview #1
Meet the Backsliders is an interview series I’m creating for anyone who’s ever wondered, “What if climbing the ladder isn’t the point?” Each interview explores how smart, driven people got tired of chasing success that didn’t feel like success and what happened when they decided to backslide on purpose.
Every Backslider featured here has shared their story with generosity and truth, in a Q&A format. Their words are their own (with light editing for tone and flow from yours truly) - with identifying details kept vague to honor privacy when requested.
Meet our first backslider: 49yo male, “unapologetic New England transplant” and 20+ year career in logistics & supply chain.
He was the “see ball, get ball, get love” kind of ambitious - until the chase nearly broke him.
This Backslider talks about letting go of status, slowing down on purpose, and realizing fulfillment matters more than a VP title. The surprising part? He didn’t lose money. He just stopped selling his soul for bonuses.
Q1: Can you describe your history with ambition? Was there someone in your life who pushed you toward being ambitious in a certain way?
Ambition - the desire and determination to achieve success.
It was never about the journey to success; it was always about the result. A friend once described my personality as “see ball, get ball.” I politely corrected her: “You forgot the part about ‘eviscerate all who stand in my way of getting ball.’”
For most of my life, I confused success with happiness.
If I’m successful, I’ll be praised. If I’m praised, I’ll be liked. If I’m liked, I’ll be happy.
See ball, get love, feel happiness.
Some of us grew up in families where the dynamic was… not awesome. Sometimes you end up thinking your job is to be the jester - to make everything easier, to make yourself disappear in the name of keeping the peace. It wasn’t your job then; you were six. You were a kid. Feeling like you have to earn love sucks. Feeling like you is too much sucks.
That was never your ball to get. And although I’m sorry that your life led you to believe that… you’re here now, and I’m really glad you’re here. I saved you a seat. Life isn’t easy or fair (that would make a boring-ass story no one would read). But holy shit… you made it this far.
In the words of Arshay Cooper: “Sit tall… you belong here.”
When I applied to graduate school (mainly because the job fair was at the same time as Ultimate Frisbee practice), I happened to read a recommendation letter from my advisor. It said:
“I think [MY NAME] will do great when given the chance to focus his attention — if that focus is what he chooses to do.”
Around the same time, I asked a friend who interned in my dad’s office what people there thought of me. “Um… they kind of think you’re all over the place, and a burnout.”
Those weren’t my father’s words (we had that conversation 25 years later), but I remember the inferno building both times. I’ll show you, I thought. I’ll show all of you.
See new ball. See enemies in the way. Crush them all. Receive praise. Be happy.
Enter Corporate America: sell soul to highest bidder. Work as many hours as it takes — as many as it takes.
Get. Fucking. Ball.
Q2: Was there a specific moment or breaking point that pushed you to think about how you defined success for yourself, or did it happen gradually?
At one point, I asked an amazing friend to coach me. It says “Difficult Patient” on my chart. I morphed my answers to get approval. I wasn’t ready.
But she asked me something that stuck: “Are you talking about success, or fulfillment?”
Sometimes, there are things in life that wait for you. You can put black tape over the dashboard lights. You can turn up the music to drown out the engine knocking. You can put new kicks on your feet and think they’re happy feet. But you’re not fooling anyone.
My friends saw it. My dad saw it. My wife saw it. My coaches saw it. I was miserable. And my daughter was growing up without me there, because I was at work all the time.
When my blood pressure hit 135/90 at age 38, my wife was inches from walking out, my eye twitched from stress, and I was taking calls on vacation - that’s when I started to think about fulfillment.
See ball… wait. Which ball? Whose ball? Why the hell do I want that ball?
You can’t go to the bank and get more time in life. When your time is up, there are no do-overs. None.
Q3: How did you decide what kind of work or environment you wanted instead?
I had tried leaving the corporate world before, and for a while, it was fun. But like prey to an anglerfish, I chased something shiny.
(Angler: someone who fishes with a rod and line.
Anglerfish: terrifying creature that lures others in and devours them with teeth made of nightmares.)
After barely navigating the action sports world (aka: the anglerfish) for half a decade, I limped back to Corporate America under the guise of “this time it’ll be different.” And it was for about six months, until the corporate goons came in and ran my new company, and its people, into the ground.
Put down “rad” ball.
See “sustainable” ball.
Grab “sustainable” ball.
Watch it shatter into sharp plastic pieces.
Then a friend told me about a small company with a flat structure. No annual reviews. The pay was comparable, but under a weird structure that wasn’t clearly defined. I wouldn’t be broke, but maybe I’d be making less?
If I worked there, I would never be a director or a VP, and anyone reading my LinkedIn profile would say “Okay, has lots of experience…really ground it out in the trenches, 6 years in each place and now he’s wait…what? Why would he take a demotion in title??”
The fear was real.
Would people think I failed? That I couldn’t hack it? Would I ever be respected again?
But the owners of this company said, “How can you do your best work if you have no balance?”
And my old boss told me, “You know what it’s like here, and you’re always welcome back. Why the hell wouldn’t you go find out what this new thing is like?”
So… yeah. I gave it a shot.
(And btw, if you’re stuck on needing everyone to respect you - go read Albert Ellis.)
Q4: What has been the hardest part about letting go of the climb — whether that was status, money, or identity? And is it a “one and done” letting go or something you have to let go of over and over?
I don’t actually believe that comparison is the thief of joy. Some trees are tall, some are short, some are old AF, some have apples on them, some have sap that tastes like childhood joy when you boil it for long enough.
Judgment about those differences - that’s what bites us.
Sure, I see old colleagues who climbed higher.
Sammy P from my first company is a Sr VP now… I used to work circles around him.
Jenny H is the COO of that place… didn’t I teach her Excel Macros?
Did I waste my potential? Was I not able to hack it? Did I finish 4th in a three person race?? Will people judge me for that? Probably.
But “Everyone MUST like me and think I did great.” - Write that down on a piece of paper and throw it in the trash. It’s false.
Some people are fighting battles that nobody knows about. I have done more work on myself in the past 7.5 years than I have ever done in my whole life.
Letting go is a lifelong quest. Success is that I keep learning. Fulfillment is that I will never stop trying.
Q5: When that gremlin voice shows up — comparing yourself to old colleagues or your past self — how do you quiet it?
I try to celebrate the success of others.
“Good on them,” I tell myself. “I hope they’re happy. I hope they find what they’re looking for.”
Sure, there’s jealousy. But there’s not a house big enough to make me put up with corporate horseshit again. Bigger house, bigger mortgage, bigger anchor into Corporate America.
Q6: What are you ambitious about these days, if not work? In other words, what has backsliding given you that the old version of success never could?
Staying on the path I was on would have led to serious health issues, a divorce, and a complete mental breakdown.
Backsliding has given me the chance to find myself, meet my wife again, see every single school performance my daughter has done in school, come in to work late on mornings during turkey season, be the guy who went from saving a company millions to the guy responsible for ordering the office coffee (and you’re damn right it’s now really good coffee) - more people smile because of the coffee.
Backsliding gave me the chance to work at a place that has a gym that I actually get to use - and gave me a chance to get my health under control.
Q7: What would you say to someone who feels trapped in a high-pressure career but is scared to take a step back?
You cannot go to the bank at the end of your life and get more time.
Nobody in a nursing home wishes they could spend one more late night in the office, or on a conference call while on vacation.
Start making your life more important to you than your time is to them.
In the words of Tyler Durden: “You are not your fuckin khakis.”
Q8: What did we miss? Anything else you’d like to share?
What you do today or tomorrow is not what you have to do forever. You’ll never get 100% of your decisions right.
If happiness depends on life going exactly how you think it should, there would be no happy people.
We all get one chance at life - live it on your own terms. Try new shit.
In the words of former UVM Men’s Basketball Coach Tom Brennan:
“I’m rooting like hell for you.”
Do you have your own story of intentionally backsliding? I’d love to hear it.
You might be in a season of intentional backsliding if:
You craved a career shift, did something about it, and now wrestle with feelings about walking away from a “good thing” especially “in this economy.” But ultimately feel like it’s a good thing!
You left the grind and feel positively about it
You’ve achieved what you thought you wanted - and now wonder… is this it?
You redirected your ambition toward other parts of your life: caregiving, health, rest, creativity, community
You’re not burned out yet, but you felt the edges fraying and you’re trying to choose a different path before the fire hits
You’re not alone and you’re not failing! You’re simply choosing to define success for yourself.
If you’d like to share your story for this Meet the Backsliders series, email me at lindsey(at)lindseylathrop.com.
I still plan on launching a small group coaching experience called The Intentional Backsliders Club, but instead of this fall, I’ll launch it in January 2026. It’s for people who are ready to think differently about success, value, and what matters right now.
I’m still shaping this coaching group, but here’s how I’m pretty sure it will be structured:
We’ll meet live on Zoom bi-weekly over 12 weeks (so 6 times)
It’ll be a small, supportive cohort of 8-12 people
Each week we’ll explore a major theme, like:
identity disruption (and potential loss of status)
fear of regret
financial & structural security
ambition redirection & enoughness
There will be time built in for self-reflection and community sharing
You’ll receive optional homework
I’ll provide light coaching during the live sessions
We’ll meet and learn from real Intentional Backsliders (I’m hoping to have them as guests)
If this sounds like something you’d be interested in, help me shape the idea!
If you’re not sure if this is for you, you’re welcome to email me at lindsey(at)lindseylathrop.com and we can sort it out.
And as always, I’m available for 1:1 coaching which you can learn all about here.
