Is working for yourself actually safer?
A guide to what really makes self-employment resilient and how to stop building a fragile business.
There’s a story we were taught.
That employment is safe.
And working for yourself is a gamble.
No paycheck. No safety net. No one to catch you if things fall apart.
You hear it in small talk. In your parents’ voices. In your own nervous thoughts when things slow down.
And it makes sense. That structure is familiar:
A salary. A title. A calendar that’s not fully yours.
You learn the rules. You follow them. You’re protected. Until you’re not.
Because in the last few years, more and more people are realising:
Safety isn’t given. It’s rented.
And the lease can be pulled at any time.
Layoffs. Budget cuts. Restructurings.
The ground is not as firm as it once seemed.
So I want to ask a different question:
What if safety isn’t found in employment or self-employment?
What if it’s not something you’re given, but something you build?
And what if most of us were never taught how?
The driving metaphor (and why it still holds)
Here’s how I often explain it:
Most of us spend our careers in the passenger seat.
We’re moving. Maybe even fast. But we’re not choosing the route.
Even if we’re senior in our roles (directors, leads, specialists) we’re still inside a system someone else designed.
A job title. A salary band. Someone else’s map.
And when we leave?
We think we’ve taken the steering wheel.
We start consulting, freelancing, contracting. A few projects come in. We’re busy.
But underneath, we’re still using the same logic:
We take whatever work shows up.
We let clients steer.
We avoid business development because it feels awkward or unclear.
That’s not driving.
That’s coasting.
We don’t have a map.
We never took a lesson.
We don’t know how to handle a sharp turn.
When I first started freelancing, I was exactly there.
I had great clients. I was being paid well. I wasn’t burned out.
From the outside, it looked solid.
But I hadn’t built anything that could hold me.
I didn’t know how to grow. Or raise my rates. Or bring in new work when referrals slowed.
If one client disappeared, I had no plan.
If I got sick, I had no backup.
If someone asked what I did, I stumbled.
If I looked six months ahead, I saw fog.
And honestly?
I didn’t want to learn to drive.
I just wanted to keep coasting.
To do good work quietly. To trust that more would come.
But building something safe doesn’t come from coasting.
It comes from learning to drive.
Even when it’s uncomfortable.
Even when it means trading current money for future stability.
Why we don’t learn to drive
Here’s what I’ve seen, over and over:
We’re not taught to think of work as something we can design.
We’re taught to be excellent.
To deliver. To stay useful. To please.
We become experts.
But usually, someone else does the selling.
So when we go out on our own, we still deliver brilliantly.
But we don’t always know how to:
Translate our work into outcomes decision-makers care about
Most websites talk about us, not what changes for the client. No clear outcome or transformation, and therefore no clear value.
Spot opportunities to retain, deepen, or grow
We finish one project and go find another. Instead of staying in the room and building and expanding our relationship strategically.
Connect our offer to a clear business case
We lack a clear articulation of ROI: time saved, money made, risk reduced or growth unlocked, and so what we offer feels like a nice to have and gets delayed.
Protect time to grow, not just deliver
We’re fully booked, and busy. Every hour goes to client work, with no space to reflect, follow up, or build a pipeline.
It’s a skills gap.
But more than that, it’s a design gap.
And the longer we avoid designing intentionally,
The longer we stay in no man’s land:
Independent, but not empowered.
Working hard, but not building anything.
Choose your discomfort
Here’s what’s uncomfortable:
Building something safe takes effort.
It means questioning what makes you valuable.
It means saying no. Rewriting old stories.
Investing before you feel ready.
And I get why that can feel like too much.
Many people are already tired. Already stretched.
They want clarity, not complexity.
So they choose the other discomfort:
A sense of instability.
A fragile business model.
Constant anxiety about where the next thing comes from.
Always feeling a little behind, a little exposed.
Most people don’t realise they’re choosing it.
But they are.
Discomfort is inevitable.
The question is: what kind of discomfort will move you somewhere better?
Let’s get specific
❌ What makes self-employment fragile?
One income stream
One client. One contract. When it ends, everything wobbles.
If your business stops when you’re fully booked, it’s not a business, it’s a job without benefits.
No protected time for business development
You’re too busy delivering to plant new seeds for what comes next.
A reactive model
You take whatever comes your way. Your pricing is shaped by what others will pay, not what you need to thrive.
Fuzzy positioning
You can’t describe what you do without listing ten things. And it’s not clear why someone would choose you.
An employee mindset
You still wait for work. You don’t set terms. You’re waiting to be chosen, not choosing.
✅ What makes it safer?
Diversified income
Multiple clients. Different types of offers. Not all eggs in one basket.
A clear model for how you make money
You understand how your business creates value and how to explain that to others.
Time carved out to work on your business
Even one or two hours a week to reflect, plan, nurture relationships, and follow up.
Positioning that connects your work to real outcomes
You lead with outcomes, not process or experience. You make it easy to say “yes.”
You can get new work when you need to
You know where clients come from, how to reach them, and how to move them forward.
This is what I mean when I say I now feel safe.
It’s not that I have everything figured out.
It’s that if I needed to earn money quickly, I’d know where to start.
If I needed to pivot, I’d know how to test.
If I wanted to grow my audience or launch something new, I have the skills and the tools.
I know how to drive, not just sit in the car.
It’s not control or certainty.
It’s capability.
And that makes all the difference.
If you’re here, reflecting...
Start small. But start. Here are three aspects I suggest exploring:
1. Look at your income.
Is it coming from one place? What would it look like to add just one more stream?
2. Audit your week.
Are you spending any time on business development or nurturing relationships - or just delivery?
3. Review how you talk about your work.
Is it about you? Or the outcome? Is it clear who it’s for, what it changes and why it matters now?
One last thing
Working for yourself can feel fragile. Especially at the start.
But fragile doesn’t mean broken.
It means you’re still building.
And the good news is: you can learn how to drive.
Not just to get by
But to go where you want to go.
Because safety isn’t a salary.
It’s knowing what to do when things change.
And in a world where change is constant,
That might be the most valuable skill of all.
Want to build this kind of safety?
At IMMA, this is what we work on every week, together.
If you’ve been meaning to get clearer, braver, or better supported in building your business…
Don’t wait another six months to feel more in control.
Because the cost of waiting isn’t just financial. It’s emotional.
You deserve better than uncertainty on repeat.
And you don’t have to build it alone.
Behind the scenes at IMMA Collective
It’s been a few exciting and busy weeks at IMMA.
We’ve welcomed Andrea dos Anjos Pinto as a Community Leader. She’s a strategist, facilitator, and community builder with over a decade of experience leading initiatives across Latin America and Europe. With a deep focus on systems change, migration, and belonging. She brings the kind of depth that makes communities not just active, but transformative.
We’re redesigning everything — our website, our offers, our rhythms — around one clear goal: helping our members consistently get aligned clients so they can increase their income, focus on what they do best, and grow a business that’s built to last.
Thinking about going independent? Join me and Caroline Harris for a workshop on how to explore that shift without burning bridges or blowing up your life. Reserve your spot →
Thanks for reading.
If something resonated — or raised a question — feel free to hit reply. I’d love to hear what it sparked.
Lilli
Founder of IMMA Collective
Brilliant article, thank you, I needed to read this today!