From SVP to SWDYDN (So What Do You Do Now?) – The Executive‑to‑Entrepreneur Identity Crash
I spent 25 years in corporate.Big titles. Big meetings. Big opinions about things like PowerPoint.
I honestly thought leaving would be the easy part.
I’d watched so many people get stuck on their way out that I was pretty sure I’d cruise right past that exit ramp. I knew the politics. I knew the patterns. I knew exactly where everyone else tripped.
And then I left to start my first business in 2014 (my branding agency, Double Dutch).
And wouldn’t you know…I tripped in the exact same place.
Turns out, corporate conditioning doesn’t evaporate the moment you turn your laptop in. It comes with you and keeps whispering, “Remember, we must be polished, poised, and perfectly on message all the time!”
Life After Title – The Part No One Mentions
In corporate, your identity is basically done for you:
- Your title says who you are.
- The org chart says where you belong.
- Your calendar says how important you are every 15 minutes.
You don’t have to explain yourself. “VP of Something Impressive” does all the heavy lifting.
Then one day you’re “founder,” “consultant,” or “I swear I do an actual thing, just give me a second to explain it” – and it’s just you and your toothless pug, Penny (or at least that’s how it was for me) and suddenly:
- Your LinkedIn headline box feels likes it’s disappointed in you
- You rewrite your bio 47 times and it still reads like a performance review.
- Your calendar is wide open…and really, really quiet.
- You miss the days when people just saw your title and knew where to file you in their brain.
Sure, you keep reminding yourself, “You chose this because you want meaning and impact and balance in your life!” And yet, getting your new work out into the world feels weirder and harder than it should.
Ask me how I know.
How Corporate Conditioning Follows You Home
Here’s what I see over and over with executives‑turned‑entrepreneurs (including…hi, me):
- You introduce your resume instead of yourself.
Every conversation starts with “Well, I spent 20–25 years at…” and by the time you get to what you actually do now, everyone’s mentally checked out. - You work like a senior leader – and like you’re doing a favor for a friend.
Caymus experience at boxed‑wine prices. - Visibility feels…beneath you and terrifying at the same time.
You used to present to boards. Now posting on LinkedIn as “just you” feels like showing up to a meeting in your only your undies…fully exposed and definitely not on the agenda. - You accidentally rebuild corporate inside your business.
14‑step processes, three “service lines,” overcomplicated offers – all in a one‑person company. Simple feels suspicious, so you make it complex and exhausting instead.
That’s not because you’re bad at entrepreneurship. It’s because you were very, very good at being corporate. Your brain is just running old software in a new job, where the rules are…well, there are no rules.
The Moment I Realized “Oh… I’m Stuck Too”
My ripped‑from‑my‑own‑headlines moment came the first few times someone asked:
“So, what do you do now?”
In my head:“Easy. I help executives translate their experience into a brand people want to hire. I know exactly where they get stuck and how to fix it.”
Out of my mouth:
“Well, I was in corporate for 25 years and I did [insert long history lesson] and then I decided to start my own thing and now I kind of do strategy, consulting, some coaching, a bit of this, a bit of that…”
If you’ve ever heard yourself give a 4‑minute TED Talk to answer a 4‑second question, you know the feeling.
That’s when I realized – I wasn’t special. I wasn’t immune. I was stuck in the same place as everyone else:
Trying to sell “Former Executive” instead of clearly talking about what I actually do now.
Corporate conditioning: 1Me: humbled.
From Former Fancy Title To Current Actual Value
Here’s what I see work best for my fellow corporate escapees who do get traction:
- Treat your resume as evidence – not your whole personality.
Your 25‑year track record is proof you can deliver. It’s not the only interesting thing about you. You get to reference it without living there. - Translate, don’t reinvent.
You don’t have to become a totally different person. You’re taking skills you’ve been paid very well for and putting them in new packaging – clear problems, specific outcomes, simple offers. - Let your voice be your voice.
You no longer have to sound like a corporate memo that passed through Legal. You’re allowed to have opinions, stories, and…jokes. Trust me, your people can handle it.
This is the part where your brand stops sounding like your old company – and starts sounding like you, on your sharpest day.
A Few Questions To Save You Some Pain
If you’re somewhere in this “identity hangover” stage, try these on:
- If you weren’t allowed to mention your old title or company, how would you explain what you do in one sentence – to a smart friend over coffee?
- What are the 1 – 3 problems clients would happily pay you to solve?
- When someone says, “Working with you was worth every penny,” what changed for them that they can’t unsee or un‑know?
- Where are you still performing Corporate You, instead of letting Founder You be in charge?
You don’t need a perfectly polished answer. You just need honest ones. The polish can come later. (Preferably not in the form of 37 page slide deck.)
Why I Care So Much About This
I know what it’s like to be the go‑to person inside a company – and then feel weirdly lost the minute your email address changes.
I also know you didn’t spend decades building a career just to tiptoe into entrepreneurship like, “Um, hi, sorry to bother you, I might be good at this?”
You are not starting from zero.You are starting from 25 years of data.
My goal – in everything I write, teach, and build – is to save you as much of the unnecessary identity drama as possible. To help you skip the “I am my title” hangover and get to the part where you can say:
Here’s what I do.Here’s who I help.Here’s why it matters now.With a straight face. Maybe even a little bounce in your step.
No badge. No org chart. Just you – and the business you actually came here to build.
Look, you didn’t leave corporate just to recreate it in yoga pants. You left because some part of you knew, “I’m the one who made that title valuable, not the other way around.”
The moment you start acting like that’s true – in your pricing, your positioning, your presence – is the moment this stops feeling like a meltdown and starts feeling like the life you actually wanted.