You didn’t think entrepreneurship was in the cards. After over 20 years in corporate, you figured you’d stay until retirement, or just never retire.
Then the layoffs started. Maybe you got caught, spent 8 months sending hundreds of resumes into the void, and realized: the ageist job market isn’t going to let you back in.
Many people in midlife lurch toward entrepreneurship, feeling forced, unprepared, and intimidated. Most successful solos didn’t wake up one day with confidence. They learned as they went.
Over the next 3 episodes, we’ll take a clear look at entrepreneurship. Today, we’ll unlock resistance. Next time, you’ll learn how to identify your archetype so you can figure out which path fits best. Then based on that, I’ll share ideas for taking action.
First, let’s look at resistance itself.
What Reluctance Is Trying to Protect You From
Most of the time, resistance to starting your own business is a protective measure. You imagine financial scarcity, loss of structure, judgment from peers.
And yes, lumpy income is something to manage. Implementing structure can feel scary if you’re starting from a blank page.
What I find is that people fear these things in the abstract. But when you have a concrete idea, the calculation looks different:
You get to hang out with dogs all day and never go back to an office. In return, you’ll have some unpredictable income months and you’ll need to figure out your own schedule. Are you up for that?
That sounds a lot more manageable than the vague terror of ‘entrepreneurship.’
People also forget the current corporate reality: a steady paycheck can be stopped at any moment. Structure in a job can change with one flick of a re-org.
Ok fine, you say. I can imagine the upside, but I’m not cut out for all the administrative work.
Aren’t you?
Admin tasks are not monsters
Mid-sized and larger companies manage payroll, HR, IT support, and healthcare. Even if you think your company handles all of that poorly, you’re relieved you don’t have to. Because you don’t really know how it works, you might believe you are incapable of handling that administration.
Aren’t you the same person who planned a complex vacation for warring family members? You’ve already figured out far more complicated things than invoicing a client and paying some bills.
Try not to assign too much power to the admin around a business. Don’t make it the monster that stops you from going out on your own.
Besides, the term ‘solopreneur’ is misleading. You’re not alone; there’s an ecosystem of tools designed to handle what used to require a team:
Accounting tools like Wave make invoicing painless. Website platforms like Squarespace let you look professional in an afternoon. AI tools can brainstorm with you at 2am when you’re stuck.
And here’s what surprised me after 5 years: I thought I’d outsource accounting immediately, but the tools are easy enough that I never needed to.
Once your mindset begins to shift from ‘I can’t’ to ‘I could,’ that’s when you see opportunities and dive in.
But why do you still resist? Don’t worry, it’s totally normal.
Examine the Roots of Your Resistance
We are wired for consistency. To fight against change at every turn. When we peel back all of the excuses for not making a change, we are left with the fear of loss.
Leaving the corporate world is scary. The routine and the people are familiar. You’re really good at navigating the system, even if it’s terrible. You are responsible for big projects. You like your office.
AND you can be laid off tomorrow.
People aren’t scared of entrepreneurship; they’re scared of losing the identity that made them successful in corporate life. You’re great at managing the systems, at figuring out how to get things done, knowing the exact right person to call so you can unblock something.
The fear you feel when you think about losing all of that could trick you into thinking you are a “big company person.” But all of that was an adaptation. Your discomfort will be temporary, and your freedom is the antidote.
You have the opportunity to get back to who you were all along.
You learned a lot of weird jargon in your last job. You can learn how to run a business.
And if you have stereotypes about entrepreneurs and worry about becoming one of them, they can be reframed, too. You won’t be a smarmy salesperson, but someone who believes in the value of what you offer. You won’t be a shark, only someone determined to give this a try and not go back to a big company.
Everything you’re worried about losing, you can grieve and then replace.
And even better news: you are not the first person to become an entrepreneur! An entire industry is waiting to support you through this transition.
Communities That Support Reluctant Entrepreneurs
Community is critical. You need people who get it–who won’t look at you like you’re crazy when you talk about your idea. Here’s where to find them:
SCORE from the Small Business Administration gives you free mentorship from people who’ve done this before.
BNI and networking groups can offer warm intros.
Co-working spaces give you a built-in community of builders.
And Reddit’s entrepreneurship threads? Anonymous, real talk when you need it.
Coaching and the Mindset Shift
This transition is as much identity work as it is skill-building. You’re moving from waiting for permission to giving it to yourself. From fitting into someone else’s systems to building your own.
It’s normal to grieve the version of you who knew exactly what to do inside a big system, even if that system wasn’t working anymore.
Some people do this on their own. Others find that a coach or accountability partner keeps them from spiraling into ‘I can’t do this’ mode. Either way works; just know what you need.
The start of your future
I love learning about cognitive biases. A relevant one here is the End of History Illusion. It’s this tendency we all have to recognize how much we’ve changed in the past – all the adaptations we’ve made, the skills we’ve learned, the versions of ourselves we’ve outgrown – but then we turn around and believe we’re done changing. That who we are right now is who we’ll always be.
You can look back at your 25-year-old self and think ‘wow, I was so different then.’ But when you think about your future self? You assume you’ll basically be the same person you are today, just older.
That’s the bias talking. You’ve already proven you can adapt and change. You learned corporate lexicon, you navigated politics, you became an expert in systems that didn’t even exist when you started your career.
The you who’s scared of entrepreneurship right now is not your final form either. You’ll change. You’ll adapt. Just like you became someone who knew how to navigate corporate, you’ll become someone who knows how to run a business.
The first step is to give yourself permission to start.
Tune in next time – we’ll dig into figuring out what kind of entrepreneur you are.
Until then, burn the map. Build what fits.
