Why I Left a Good Job to Start Two Companies

~by Haley Lynn Gray~

Last August I left a very good job. I was a manager at a large IT corporation — decent role, decent money, nothing wrong with it — and something was missing.

After some genuine soul-searching I started two companies: Extension of You Home Care, which was mine from scratch, and a Care Patrol franchise.

People ask how I knew entrepreneurship was right for me. Here’s the honest answer.

What actually drew me

Building something that reflects my own standards. In a corporate role you execute someone else’s decisions about how things should be done. I wanted the decisions.

Seeing a gap and being able to act on it. I could see how home care was being done badly — how caregivers were treated, how families were handled. In a company, noticing that is frustrating. Owning one, it’s a plan.

Control over my own time. Not less work — I work more. But the shape of it is mine, and with four children that mattered more than the hours did.

And a direct line between effort and result. In a large organisation, good work disappears into a system. In your own business the connection is immediate, in both directions.

What I’d want anyone to know first

The income stops being predictable. That’s the part people underestimate — not the amount, the variability.

You’ll do every job. Including the ones you were previously senior enough to avoid.

The loneliness is real. Nobody to consult, no colleague down the corridor, and the decisions are all yours. Peers aren’t a nice extra; they’re how you avoid your most expensive mistakes.

And the expensive lessons arrive regardless. Mine included $47,500 on a launch that produced one sale.

How to tell whether it suits you

Do you mind uncertainty, or does it genuinely frighten you? Some people are miserable without a predictable salary, and that’s information, not weakness.

Do you like deciding? Not the idea of authority — the actual work of making calls without enough information.

Can you sell? Or are you willing to learn? Nothing else matters if nobody buys.

And are you drawn to a specific problem, or just to the idea of working for yourself? The second one isn’t enough to survive year two.

Would I do it again

Yes. I sold both of those businesses eventually, and I’ve built others since.

The thing I’d tell my earlier self is that leaving wasn’t the brave part. The brave part was the ordinary stretch afterwards — the months of doing unglamorous work with no certainty it would amount to anything.

If that sounds appealing rather than alarming, you probably have the temperament for it.

If this resonates, you don’t have to figure it out alone.
We host small, thoughtful Round Table conversations inside Women’s Entrepreneur Network where women leaders talk through exactly this kind of challenge.
You’re welcome to join us.

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