What To Do When You Are Being Held Hostage

Yesterday, January 6th, the first Monday after the holidays. While the rest of the world returns to its normal routines, filled with “circling back after the holidays,” you, the entrepreneur, are still shouldering the same amount of responsibility.

Maybe you managed to take a few more days off than usual, and the world felt a bit quieter, but having a business—while it offers a freedom most people can’t understand—also comes with a unique weight and responsibility that can often feel isolating.

It’s hard to explain this to those around you. Your friends might be disillusioned with their jobs, complaining about their bosses or pointless meetings. Sure, you can work anytime and in sweatpants, but even as the expert and core of your business, there’s a constant sense of uncertainty in your day-to-day life.

From wearing so many hats—managing the money, learning QuickBooks, building your website—to dealing with unexpected setbacks like a plugin that crashes your site and inexplicably turns everything green, the challenges never end.

Take social media, for example. Once, I thought setting up a new Instagram account would take three minutes. Instead, Instagram flagged me as a potential bot or spammer, and I had to take a picture of myself holding up a notebook with my name and date written on it. I hadn’t even showered that day, but there it was: my selfie submitted to Instagram for verification.

It’s a funny story now, something I can share with my friends and partner, but most days, when someone asks how work is going, my default response is “fine.” Because honestly, where do I even begin?

How do you explain that something you thought would take 15 minutes ended up consuming an hour and a half? How do you describe spending an entire day down a rabbit hole trying to learn about SPF, DKIM, and DMARC—terms you didn’t even know existed 24 hours ago?

And let’s not forget every book you’ve read and podcast you’ve listened to lately, all of which seem to assume you’re already making millions and just need advice on how to make a million more. “Sell to your list,” they say. But what if your only follower right now is your mom?

Even successes can feel difficult to share. When you finally conquer DMARC and could practically pass a written exam on it, you’re thrilled—but your friends smile politely and give you blank stares because they have no idea what you’re talking about.

Here’s the truth: the challenges don’t go away. The more you accomplish, the more there is to learn and conquer next. But what does change is your confidence. Over time, you start to trust that you can handle whatever comes your way.

I often joke with a fellow entrepreneur friend that I’m just 20 minutes ahead of her. When she asks for help or advice, she’ll marvel at how much I seem to know. I smile and say, “I learned this yesterday.” Once you’ve done it, it gets easier, and I promise, in 20 minutes, you’ll look like an expert too.

So keep going. Keep moving forward. You’re not alone. I, and so many others, know exactly how you feel.

And remember: the “new you” is already more of an expert than you realize.