There's a particular kind of Tuesday that gets to a lot of us. Nothing dramatic happens. You answer the emails, you sit through the meeting that could've been an email, and somewhere around three in the afternoon you catch yourself thinking, "Is this it?" Not in a crisis kind of way. Just a quiet, nagging, is-this-really-what-I-signed-up-for kind of way.

I think we tell ourselves that job is the safe choice. The steady paycheck, the benefits, the predictability of knowing exactly what hours you're supposed to work. And I get it — that predictability feels like solid ground. But this week I talked with Melissa Broughton, who built a ten-year bookkeeping business after leaving corporate life, and our conversation reminded me why I've been saying this for years: that company you're building your life around could close its doors tomorrow, and you wouldn't have had any say in it at all. You don't control the schedule, you don't control the people you work with, and you definitely don't control whether you still have a job next year. Meanwhile, when you're working for yourself, you get to decide all of that. You can even fire a client who makes you want to bury your head in the sand. Try doing that with a boss.

That's not a small reframe. Most of us were taught that corporate is the safe lane and self-employment is the risky one. Melissa and I have both watched that play out over and over with the women we work with, and it holds up every time. The "safety" a lot of us are clinging to was never really ours to begin with.

So if that's true, why don't more women make the leap? Melissa's answer was fear, and honestly, that tracks with almost every woman I've ever coached. Not fear of failing, necessarily. It's the fear of the silence that shows up the first morning you wake up without somewhere to be. We are so wired around our schedules that an empty calendar can feel more frightening than a full one. Melissa told me about an exercise she uses with her own bookkeeping students, and the same one she used with her boys when they were small and anxious about something: what's the worst that could happen? You have to answer fast, before your brain has time to dress the answer up in something more respectable.

She told me about a student of hers, a retired attorney, brilliant, accomplished, who said she'd do anything except get on the phone with a prospective client. When Melissa walked her through the exercise, the answer wasn't what either of them expected. It wasn't fear of rejection. It was the feeling that she'd be wasting her time, because her entire career had trained her that her only value was her billable hours. One phone call, and one honest answer to a silly-sounding question, cracked something open that years of expertise hadn't touched.

I don't think that story is really about phone calls, or even about bookkeeping... I think it's about how much of our hesitation is actually old evidence, proof from a life or a career we've already outgrown, still running the show. And I loved that Melissa's whole business exists to prove the opposite is true. She built a training system on the idea that most of us already have the skills we think we're missing: running a household, keeping track of a family's moving pieces, knowing when something looks off in a budget. That's not nothing. It's most of the job. Someone just has to show you how the dots connect.

Melissa didn't quit cold and hope for the best, and I appreciated that she was honest about that. She and her husband built toward the leap: figuring out the number that covered their needs, then the number that let them actually live the life they wanted, and closing that gap a little at a time before they walked away for good. Reinvention doesn't require recklessness. It requires a plan you trust enough to follow one small step at a time, and the willingness to ask yourself the question underneath the fear instead of just letting the fear win by default.

If you're sitting with your own version of that quiet Tuesday feeling, I'd gently ask you the same question Melissa asks her students. Not "should I do this someday." Just: what's the worst that could happen if you did? Say the real answer out loud, even if it sounds a little silly. Especially if it sounds a little silly. That's usually where the truth is hiding.