How to take the leap before you feel ready

Any opinions, views, findings, conclusions, or recommendations expressed in this publication are those of the author(s) and do not necessarily reflect the views and policies of Hiscox.

In 2005, I opened Sprinkles Cupcakes in Beverly Hills — just cupcakes, nothing else — right in the middle of the low-carb craze, when half of Los Angeles was convinced sugar was the enemy. People around me — friends, locals, anyone who’d hear me out — wondered if a single-item bakery was too limiting, or whether LA customers would ever line up for something so indulgent. And my own internal voice had plenty of doubts too. I was a first-time founder with no retail experience, baking out of my home kitchen, about to sign a lease on a commercial space in one of the most expensive zip codes in the country.

I wasn’t ready — but I did it anyway. And none of what followed would have happened if I’d waited until I felt ready.

Here’s what that leap taught me

1. Readiness is a moving target

What I had instead of certainty was conviction. I genuinely believed the world needed a better cupcake — one made with premium ingredients, baked fresh daily, presented beautifully. Not an afterthought sitting on a bakery shelf, but the main show. I couldn’t get the idea out of my head. I was obsessed. And eventually I realized that the obsession itself was a signal worth listening to. So I signed the lease, bought the equipment, and started baking at 4am. You’ll never have enough capital, enough experience, or enough certainty. At some point, you have to decide that what you have right now is enough to begin. The founders I admire most didn’t wait for permission — they started with what they had and built from there.

2. Doubt is not a stop sign

The first week, a line formed down the block. Word traveled fast through the neighborhood, then into the broader city — the kind of organic buzz that advertising can’t buy. Regulars started bringing friends. We started getting calls from event planners, from offices wanting to treat their teams, from people who’d heard about us secondhand and driven across town just to see what the fuss was about. None of that felt inevitable when I was standing in my home kitchen wondering if I was making a terrible mistake. The voice that says are you sure about this? isn’t telling you to quit — it’s telling you to pay attention. Use it to stress-test your idea, pressure-check your assumptions, and then move forward anyway. A little healthy fear means you’re taking it seriously, not that you should back down.

3. Your conviction is data

Entertainment industry assistants — who, trust me, always know where the best food is — started placing orders for their clients. One of those clients mentioned us to a producer. That producer mentioned us to a publicist. And on it went, each connection opening the next door, until eventually Oprah called. Then we opened a second location, then a third, and then eventually we added a cupcake ATM on the side of the building, because... why not? If you can’t stop thinking about an idea — if it keeps coming back even when you try to talk yourself out of it — that persistence means something worth taking seriously. It’s not a guarantee of success, but it’s a signal that deserves more than a passing glance — sit with it.

4. The market doesn’t reward waiting

The job market right now is pushing a lot of people toward entrepreneurship for the first time, and many of them are wondering if it’s the right moment. And truly only you hold the answer to that question. But waiting for the right moment is its own kind of risk, because opportunities don’t hold their breath while you get comfortable with the idea. While you’re perfecting your plan, someone else is out there learning from their imperfect one. Starting messy and iterating beats waiting for perfect every time — and the lessons you learn in the first six months of actually running something are worth more than any amount of planning. The low-carb era didn’t last forever. Neither will this window.

Start before you’re ready — and figure it out as you go.