Escaping Corporate Isn’t The Hard Part. This IsThe Escapee Insider is a weekly-ish newsletter focused on helping folks transition from corporate to solopreneurship
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The Two Biggest Problems I See for New Escapees
When I first left corporate, I thought the hard part was quitting or more accurately leaving corporate behind since corporate quit on me.
I was wrong.
The hard part was waking up every day with no map, no team, and no one to ask, “Does this make any sense?”
Looking back, almost every struggle I had (and every struggle I see now in new escapees and solopreneurs) comes back to two things:
The learning curve which = time to making money
Isolation
1. The learning curve problem
Corporate trains you to be good at your role and how to play the game.
It does not train you to:
Design and price a service
Talk about what you do without feeling salesy
Find clients without a brand name behind you
Decide which tools, systems, and platforms you actually need
Make money in ways that aren’t a salary
Most people try to fill those gaps by piecing together:
Random LinkedIn posts
Podcast episodes
YouTube videos
A course or two they never quite finish
It’s all “information.” Very little context. Almost no feedback.
The people who move the fastest aren’t smarter. They just don’t try to learn all of this in a vacuum. They spend more time in rooms where they can ask:
“Here’s my offer draft—what’s missing?”
“Is this price completely off?”
“What would you do next if you were in my shoes?”
That’s where learning actually speeds up.
2. The isolation problem
The other piece is quieter but just as brutal: going solo is lonely.
In corporate, there’s always someone around:
The person you vent to after a bad meeting
The Slack ping, the hallway chat, the “how was your weekend?”
The sense (even if it’s false) that you’re in it together
The day you leave, all of that disappears.
Now it’s just you, your laptop, and your thoughts:
“Am I completely crazy for doing this?”
“Is it supposed to feel this uncertain?”
“Is everyone else moving faster than I am?”
You can have a great strategy and still stall out simply because you’re doing it in your own head with no one around you who gets it.
The pattern that finally became obvious
After talking to hundreds of people—still in corporate, recently laid off, or already out on their own—a pattern became impossible to ignore:
The slowest, most painful journeys were almost always solo, DIY, figure-it-out-yourself.
The fastest, most sustainable journeys were surrounded by peers and guides:
People at the same stage
People a step or two ahead
People willing to share the ugly parts, not just the wins
Those folks still had hard days. They still made mistakes. But they didn’t stay stuck for months because they had somewhere to bring the questions and the mess.
I have yet to meet a person who couldn’t figure it out. If you had enough time, you are smart enough to break through.
That is exactly what happened to me. I didn’t have a roadmap, I didn’t have a plan, and the dumbest thing I did was not tell anyone that I went solo. You will have to learn from your own mistakes, but you can learn from the people who were there before you.
At some point, it hit me: the problem wasn’t that people were incapable. The problem was that most of us were trying to do something hard, emotional, and unfamiliar without a place to go while we figured it out.
There were courses. There were masterminds. There were random Facebook and Slack groups. But there weren’t many spaces built specifically for the escapee journey—spaces that combined real education, real connection, and real support over time.
That’s when I stopped thinking “someone should build this” and decided to actually build it.
Why this version of the Collective exists
Three years in, I realized I didn’t just want to talk about escaping corporate.
I wanted to build the place I wish I’d had when I left.
That’s what led to the current version of The Escapee Collective:
A community for any stage of the escape journey
Still in corporate and just starting to explore
Recently laid off and trying to rebuild
Already solo and aiming at $3K, $10K, $25K+ months
Monthly core sessions for each stage, so you’re not guessing what to work on next
A growing slate of specialty sessions you can pick and choose from:
LinkedIn and content strategies
Networking that doesn’t feel gross
Tools and technology that actually help
Money, pricing, taxes, and operations
Wellness, burnout, identity, and the emotional side
These aren’t big, polished keynotes.
They’re mini workshops and real conversations with people who’ve actually done it—designed so you can ask questions, get feedback, and hear how others are approaching the same problems.
And one piece I didn’t appreciate until recently: members can host their own sessions
One of the most valuable parts for members isn’t just attending sessions—it’s hosting them.
If you’ve escaped and you’ve been building for a while, you can:
Run your own sessions on your specialties (LinkedIn, podcasting, AI tools, niche expertise, etc.)
Get reps as a facilitator and speaker in a friendly room
Build awareness for your work without turning the community into a pitch-fest
Contribute back to people who are exactly where you were a year or two ago
It becomes a loop:
Earlier-stage escapees get support, frameworks, and examples.
Later-stage escapees get a place to share what they’ve learned and grow their own visibility.
Everyone gets less isolation and a much smoother learning curve.
Escaping doesn’t have to mean doing it by yourself
That’s the core belief under all of this.
Escaping corporate and going solo is about taking back control of your time, your income, and your life.
It is not about proving you can suffer through it alone.
If anything in this resonated—especially the learning curve and isolation stuff—this is exactly the gap I’ve been trying to close with the Collective. It’s not a silver bullet, and it’s not the only way to do this. It’s just the most honest way I know to address needs that weren’t being met when I started.
I won’t do the hard sell here. If you’re curious, you can read more about how it works and see if it feels like the kind of room you want to be in:
The first month is only $1 for unlimited sessions and you can cancel at any time. I want to give as many people the awareness as possible!
This Week's Featured Podcast Episode
If you know corporate isn’t for you but you can’t see a clean exit, this episode is your roadmap. Brett sits down with Sam Lee (Indie Collective) to break down how experienced professionals can build a “portfolio career” — consulting, coaching, fractional work, and productized services — without quitting their full-time job first.
Sam shares the simple frameworks that helped him build $1M+ in annual revenue through independent work for over a decade, and he explains why most people get stuck trading time for money. You’ll walk away with a practical way to tell your story, activate your network, and design an exit strategy with less risk.
Post of the Week
If you made it this far I appreciate you reading. Please let me know what else you would like to see!
Until next week
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