Decision Paralysis is the New Midlife Crisis
Why your second act should start now
I was standing in the notebook aisle of Anvil Cards, a favorite Houston stationery shop, paralyzed. There were at least 15 options, from minimalist field notes to the poppy “Team Queso” journals. I wasn’t even buying it for me—it was a gift—but the absurdity of my indecision wasn’t lost. If picking a notebook is this hard, how am I supposed to make the big life decisions?
Turns out, I’m not alone. Decision paralysis is a modern epidemic, especially for those of us in midlife, balancing careers, families, and the quiet realization that maybe we’re ready for something new, whether it’s a new side hustle, a new school for our kids, launching our dream business or even something as recoverable as a new haircut. But instead of taking the leap, we spend months—sometimes years—stuck in the “what if” loop, wondering if now is the right time to start over. Spoiler alert: it is.
The Midlife Crossroads
Midlife used to be about fast cars and questionable haircuts. Now, it’s about existential dread and too many tabs open on your browser. According to a recent study, 50% of people aged 40-55 feel “stuck” in their current career paths, but less than half take steps to change it. Why? Analysis paralysis.
The explosion of choices—careers, side hustles, hobbies, even which streaming service to watch—makes committing to anything feel overwhelming. And it doesn’t help that social media is packed with highlight reels of people who seem to have figured it all out.
But here’s the kicker: waiting doesn’t make the decision easier—it just burns time. And time, as every motivational speaker and insurance commercial reminds us, is a non-renewable resource.
Why We’re Stuck
1. Fear of Failure
Starting something new feels risky, especially when you’ve already built a life you don’t want to blow up. But here’s the thing: failure is the currency of success. My first company failed, and Hello Alice wouldn’t be what it is today without those learnings. I even did a TED talk on failure. It’s not my best speech, but hey, it paved the way for better ones.
2. Overwhelming Options
Do you launch a business? Go back to school? Move to the countryside and start a goat yoga farm? The sheer number of paths makes standing still feel like the safest bet. But let’s be real: indecision is just a decision to stay the same.
3. Perfection Paralysis
Earlier this week, I wrote about waiting for the “perfect” idea, timing, or conditions. Newsflash: perfect doesn’t exist. What does exist is momentum—and you can’t build that by standing still. Sometimes, it’s best to rip that Band-Aid off and, in the words of Nike, Just Do It. Take that leap of faith and don’t look back.
Now is the Time
1. The Economic Landscape is Ripe
The gig economy is booming, and technology is making it easier than ever to start something new. Platforms like Fiverr, Etsy, and Substack are empowering millions of people to monetize their skills. Meanwhile, 80% of Americans are open to supporting small, independent businesses. Translation? There’s never been a better time to bet on yourself.
2. AI is Changing the Game
AI isn’t just for tech bros. It’s democratizing access to tools that used to cost a fortune. Whether you want to write a book, design a product, or start a consulting gig, AI tools like ChatGPT and Canva are your new best friends.
3. The Pandemic Reset
The pandemic gave us all a taste of what life could look like outside the 9-to-5 grind. It’s no coincidence that nearly 5 million new businesses were started in the U.S. in 2021, a record-breaking year. People are realizing that life is too short to stick with what’s comfortable but unfulfilling.
How to Break Free
1. Start Small
You don’t have to quit your job or sell your house to take action. Start with one small step: research an idea, take a class, or test a side hustle.
2. Redefine Success
Success isn’t about hitting a home run your first time at bat. It’s about building something meaningful, even if it starts small.
3. Build a Support System
Find a mentor, join a community, or start sharing your goals with friends. Accountability turns vague dreams into actionable plans.
4. Accept Imperfection
Remember, the greatest ideas often start messy. As Reid Hoffman, co-founder of LinkedIn, famously said: “If you’re not embarrassed by the first version of your product, you’ve launched too late.” Trust me when I say my cofounder, Elizabeth Gore, and I were embarrassed with v1 of Hello Alice back when we launched in 2017.
Start Messy, Like These Real-Life Inspirations
Consider the story of Julia Child. She didn’t start cooking professionally until her late 30s, and she didn’t publish Mastering the Art of French Cooking until she was nearly 50. Or take J.K. Rowling, who was rejected by 12 publishers before Harry Potter became a global phenomenon. These aren’t exceptions—they’re proof that a second act is often where the magic happens.
Replace that moment in the notebook aisle — whatever your version of it is — with something bigger: a career change, a side hustle, a life shift you’ve been too scared to make. Decision paralysis might be the new midlife crisis, but it doesn’t have to win.
Start messy. Start scared. Start now. Because your second act isn’t going to write itself—and trust me, the first page doesn’t need to be perfect. It just needs to start.
Noteworthy & New
Things that stood out, stood up, or stood the test of my curiosity this week:
“Easily distracted by rocks” hat: Perfect for anyone who finds themselves veering off the trail to inspect shiny things, this declaration of priorities feels perfect for the ADHD in me. And with 748 ★★★★★ Etsy reviews, I’m clearly not alone. 🧢
“Where Humans Still Have the Edge on AI”: Luckily, we humans still have some value in the world when it comes to emotion, complexity, physicality and creativity. Way to go, people! 💪
“A Way Foward Forward For a World Where Truth Has Died”: Forget chasing some mythical "absolute truth" – what people really want is meaning. Frameworks that help us understand the chaos of life, those are the real MVPs. It’s about making sense of our struggles, not about having the "right answer."
Automate your presentations with Gamma: Along the theme of working smarter, not harder, this year, Gamma just keeps moving up my list of go-to AI tools. The interface is ridiculously intuitive — perfect for when I don’t have time to fuss over the details — and the end result looks clean, modern, and impressive in those moments when everyone expected less from me. Consider me hooked.
