~by Haley Lynn Gray~
I left a good corporate job to start two businesses, and I’d do it again. But there’s a great deal I’d tell anyone standing where I stood — most of it about the months either side of the leap rather than the leap itself.
Before you leave
Know your number, and your runway. What you need to live on monthly, how much you have, and therefore how many months you get. Write it down. It’s the single most useful piece of paper you’ll produce.
Sort out anything that needs a salary. Mortgage, refinancing, credit — all considerably easier to arrange while employed. Do it before you resign, not after.
Understand what you’re giving up. Health insurance, retirement contributions, paid leave. Price them, because they’re real costs your new business has to cover.
Test the idea while you’re still paid. Evenings and weekends are exactly when you can afford to find out whether anyone will buy. Find a first customer before you need one.
Set up the structure. Entity, business bank account, basic bookkeeping. Dull, and much harder later.
And leave well. Notice, handover, no burned bridges. Former colleagues become clients and referrers surprisingly often.
The first month out
Nobody tells you what to do, and that’s harder than it sounds. After years of meetings and priorities set by others, the empty calendar is disorienting. Build your own structure in week one — working hours, a start time, somewhere to sit.
Spend the first month selling, not preparing. The temptation is logos, websites, business cards — all of which feel productive and produce nothing. Talk to potential customers instead.
Tell everyone you know. Specifically: what you’re doing, who it’s for, and what a good introduction looks like.
Expect the loneliness. No colleagues, no corridor conversations, nobody to check a decision with. Find peers immediately — it’s the thing most people leave far too late.
And keep an eye on the money weekly. Not monthly. Cash moves faster than you expect in the early months.
The good, the bad and the ugly
The good: the decisions are yours, the effort connects directly to the result, and you can build something that fits your life rather than the reverse.
The bad: income becomes unpredictable — that’s the part people underestimate, not the amount but the variability. You’ll do every job, including the ones you were senior enough to avoid. And you’ll work more, not less.
The ugly: the months where nothing works, the expensive mistakes, and the fact that if you stop, everything stops.
Is it worth it?
For me, yes. But the honest test isn’t whether you like the idea of working for yourself — plenty of people like that idea and dislike the reality.
It’s whether you can tolerate uncertainty, enjoy deciding without enough information, and are willing to sell. If that sounds appealing rather than alarming, you probably have the temperament for it.
Leaving isn’t the brave part. The ordinary stretch afterwards is.
