Greg Adams
DEEP DIVE
I just turned 63 on Halloween. And you know what? I don't feel like I'm winding down—I feel like I'm just getting started.
If you're reading this, chances are you've felt the same frustration I have. You've spent decades building expertise, solving problems, managing teams, and running operations. But somewhere along the way, the corporate world stopped seeing your experience as an asset and started treating it like an expiration date. I've done the corporate dance twice—20 years total at major utility companies—and both times, I ended up back working for myself. Not because I couldn't handle corporate, but because I finally realized: I don't need to bust my ass making someone else rich when I've got this much knowledge in my head.
That's why I'm starting "Second Act"—not just as a newsletter, but as a community for people like us who still have plenty of gas in the tank and refuse to be sidelined. Here are the seven most important lessons I've learned about building your second act, earned through starting two businesses (irrigation and water filtration), navigating deregulation chaos, and finally deciding at 63 that this time, I'm doing it my way.
1. Your "Winding Career Path" Isn't a Bug—It's Your Differentiator
What it is: That resume that looks "scattered" to HR departments? That's actually your secret weapon. My path went from utility work to electronics to irrigation to water filtration and back to telecom. Each pivot taught me something that connects in ways a straight-line career never could.
Why it works: After 10 years at the first utility company, deregulation hit and I had to pivot fast. Those "odd jobs" I did after? They taught me adaptability. Starting the irrigation company taught me customer acquisition. The water filtration business taught me how to build and sell a customer base. When I went back to Southwest Bell, I brought insights from entrepreneurship that my colleagues who'd only known corporate life didn't have. At 50+, you're not starting from zero—you're starting from a foundation of cross-functional expertise that took decades to build.
Implementation steps:
List every pivot, side hustle, or "detour" in your career
For each one, write down three specific skills you gained
Identify the patterns—what problems do you keep solving across industries?
Package this as "cross-industry expertise" rather than an inconsistent career path
Real-world application: When I built my water filtration customer base, I wasn't competing with younger competitors on price or energy. I competed on trust. Customers saw someone who'd been around, who understood systems (thanks to my electronics background), and who wasn't going to disappear after the sale (proven by my decade-long corporate stints).
Pro tip: Stop apologizing for your varied background. The 35-year-old with one company on their resume hasn't seen what you've seen. Market it that way.
2. The "Working Alone" Problem Is Real—And It's the Missing Piece
What it is: Here's the truth I'm still wrestling with: I've spent years working alone. I've been to networking groups where I didn't connect. I've worked with industry peers who felt threatened rather than collaborative. And it's the one thing that's held me back more than age discrimination ever did.
Why it matters: You can't build a second act in isolation. I've learned this the hard way. When you're working alone, there's no one to bounce ideas off, no one to cover your weak spots, no one to celebrate wins with or problem-solve losses with. The corporate world, for all its politics, gave us instant colleagues. When you're building something on your own, you have to intentionally create that support system.
Implementation steps:
Acknowledge that isolation is a strategic problem, not just an emotional one
Look for collaboration opportunities, not just networking events (there's a difference)
Seek out peers who see abundance, not scarcity—people doing complementary work, not competing for the same clients
Consider masterminds or peer groups specifically for 50+ entrepreneurs
Real-world application: This newsletter is my attempt to solve this problem—not just for me, but for all of us. I'm building "Second Act" as a community where experienced professionals can find resources, collaborators, and people who get it. Because I've realized that trying to do it alone was my biggest mistake, not my age or my experience.
Warning: Avoid networking groups that feel like "everyone's trying to sell to each other." Look for genuine community where people share resources, make introductions, and collaborate without keeping score.
3. Your Corporate Experience Is Business School—And You Already Graduated
What it is: You don't need to "learn business" to start a business. You've already seen how the sausage gets made. You've watched companies make smart moves and stupid moves. You've seen what works and what's all flash with no substance.
Why it works: I spent 20 years in major corporations watching decision-making at scale. When I started my irrigation and water filtration businesses, I didn't need an MBA—I needed execution. I knew how to read a P&L because I'd seen them. I knew how to price services because I'd watched corporate pricing strategies. I knew how to handle difficult customers because I'd dealt with internal stakeholders who were ten times worse.
Implementation steps:
Make a list of every business function you've been exposed to in your career
Identify which ones you could do yourself and which you'd need to outsource
Calculate how much you'd pay someone else to learn what you already know
Realize that knowledge has enormous monetary value
Real-world application: When younger competitors in the water filtration space were burning cash on marketing experiments, I already knew from corporate experience that retention beats acquisition. I focused on keeping customers happy, getting referrals, and building a reputation. Lower costs, higher margins, sustainable growth.
Pro tip: The corporate world taught you risk management, even if that wasn't your job title. You know how to spot red flags, avoid catastrophic mistakes, and build systematically. That's worth more than hustle.
4. You Don't Need to "Keep Up" with Tech—You Need to Use It Strategically
What it is: One of the biggest ageism myths is that 50+ professionals "can't keep up" with technology. That's garbage. You don't need to keep up with everything—you need to identify which tools actually solve your problems and ignore the rest.
Why it works: I've watched companies chase every shiny new platform while their core operations fell apart. The advantage of experience is knowing the difference between a tool and a distraction. You need a website, email marketing, maybe a scheduling tool. You don't need to be on every social media platform or use the latest AI widget unless it directly serves your business model.
Implementation steps:
Identify your top three business challenges (customer acquisition, scheduling, payments, etc.)
Find ONE tool that solves each problem
Learn that tool well enough to use it effectively
Ignore everything else until you've mastered these basics
Real-world application: For my water filtration business, I needed three things: a way for customers to reach me, a way to schedule appointments, and a way to collect payments. A simple website with a contact form, a Google Calendar, and Square for payments. Total cost: under $50/month. I didn't need a CRM, a funnel builder, or a social media manager.
Pro tip: When in doubt, ask yourself: "Would this problem exist if I had 100 customers?" If yes, solve it now. If no, solve it when you have 100 customers.
5. The Corporate "Playbook" You Keep Seeing Isn't a Personal Failure—It's a System
What it is: I've played out the same pattern twice: start in corporate, get comfortable, realize I'm building someone else's dream, leave to work for myself, then wonder if I should go back. If you've felt this, you're not unstable—you're recognizing a fundamental incompatibility between how corporate treats experienced workers and what you actually want from work.
Why it matters: The corporate world has a playbook for 50+ workers: manage you out, reduce your autonomy, or make you feel like you're slowing down the "young, hungry team." After experiencing this twice, I realized it's not personal—it's structural. They don't want to pay for your experience because they've decided they can get cheaper labor. That's their loss and your opportunity.
Implementation steps:
If you're still in corporate, recognize the signs: being passed over, losing interesting projects, hearing "we need fresh perspectives"
Start building your exit plan while you still have income and benefits
Use your remaining time to document everything you know
Build relationships that will become clients or referral sources after you leave
Real-world application: When I left Southwest Bell the second time, I knew it would be the last time. Not because I couldn't handle corporate, but because I'd finally learned that I could make good money, have more freedom, and actually enjoy my work by leveraging my expertise directly.
Warning: Don't wait until you're pushed out. Leave on your terms with a plan. The best time to start building your second act is while you still have a paycheck.
6. Your Customer Base Is People Who Value Experience Over Discounts
What it is: When you're 50+, competing with younger, cheaper competitors is a losing game. Instead, you target customers who specifically value what decades of experience brings: reliability, judgment, and the wisdom to anticipate problems before they happen.
Why it works: In both my irrigation and water filtration businesses, my best customers weren't looking for the cheapest option—they were looking for someone they could trust to do it right the first time. They'd been burned by the cheaper guys who disappeared or screwed up. They wanted someone who'd still be around for follow-up service.
Implementation steps:
Identify client segments that prioritize quality and reliability over price
Typically: established businesses, homeowners 45+, companies with compliance requirements
Price accordingly—your experience commands premium rates
Emphasize longevity, follow-through, and expertise in your marketing
Real-world application: My water filtration customers paid 20-30% more than my younger competitors charged. Why? Because I showed up when I said I would, I explained things clearly, and I'd been doing this long enough that they trusted my recommendations. I wasn't the cheapest option—I was the smart option.
Pro tip: If you're competing on price, you're marketing to the wrong customers. Find the people who've learned that cheap usually costs more in the long run.
7. Your Second Act Isn't a Downgrade—It's a Design Upgrade
What it is: The narrative around later-career changes is all wrong. It's not "starting over" or "settling." It's taking everything you've learned and building something designed around how you actually want to live now. At 63, I'm not starting from scratch—I'm building on 40+ years of foundation.
Why it works: Your priorities at 50+ are different than they were at 30. You're not trying to prove yourself. You're not grinding for some future payoff. You want meaningful work, decent income, and time for life. That's not "slowing down"—that's finally being smart enough to design work around life instead of life around work.
Implementation steps:
Start with the life you want: How many hours do you want to work? What do you want to make? What do you never want to do again?
Build a business model that supports those constraints
Be willing to make less than corporate paid if it means exponentially better quality of life
Remember that "enough" is a perfectly valid financial goal
Real-world application: I'm not trying to build a massive company at 63. I'm building something that lets me work with interesting people, solve problems I enjoy, and have time for my life. If that means I make $75K instead of $120K but work 25 hours a week instead of 55, that's a win.
Pro tip: The goal isn't to replicate your corporate salary—it's to build something sustainable that fits your life now. Your second act should feel like liberation, not a lesser version of your first act.
Where We Go From Here
I'm 63, I'm starting something new, and I'm absolutely certain I'm nowhere near finished. The corporate world might be done with us, but we're not done creating value, solving problems, and building things that matter.
This newsletter, "Second Act," is my way of building what I wish I'd had years ago: a community of experienced professionals who refuse to be sidelined, who see their decades of expertise as an advantage, and who are ready to build second acts on their own terms. We're going to share resources, strategies, real stories (including the failures), and connect with people who get it.
If you've felt stuck working alone, if you've watched younger colleagues get opportunities you're more qualified for, if you've ever thought "I could do this better myself"—you're in the right place.
Forward this to someone who needs to hear it. Reply and tell me your story. Let's build something together—because that's the one thing I finally learned: we're better when we're not doing this alone.
Here's to the second act. And the third. And however many more we've got in us.
— Greg
Second Act
P.S. — What's the biggest challenge you're facing in building your second act? Hit reply and tell me. I read every response, and your story might be exactly what someone else needs to hear in a future newsletter.