What Turning 40 Taught Me About Saying Yes—and Learning When to Say No
- Alyxandra Sherwood
- Aug 7
- 6 min read
Lessons from teaching, running, marketing, and building a personal brand.
On Saturday, I turn 40. Ten years ago, I was 30 years old and saying "yes" to just about everything. Looking back, I had no idea how many of those ordinary decisions would quietly shape the next decade of my life. None of them felt particularly significant at the time. Now they feel like the beginning of everything.
Saying Yes to Teaching
Ten years ago, my undergraduate academic advisor called with an unexpected opportunity. A faculty member at SUNY Geneseo needed someone to teach a Principles of Public Speaking class on short notice. I had defended my master's thesis the year before, and suddenly I found myself standing in front of a classroom twice a week wondering whether I actually knew enough to teach.
I said yes.
Around that same time, I was training for the New York City Marathon. It was only my second marathon, but my first had humbled me enough to realize that simply running more miles wasn't enough. So I hired a coach. Looking back, it was one of the smartest investments I've ever made. Experience had taught me that determination can only take you so far. Sometimes you need someone who's already run the course to help you avoid the mistakes they made.
That same year, Ryan and I celebrated our fifth wedding anniversary. I attended my first professional conference in St. Louis. Life was moving quickly.
Teaching
Running
Marketing
Marriage
Each milestone felt unrelated. At the time, I couldn't see how connected they really were.
The Bigger Lesson
When we look back on our careers, it's tempting to focus on promotions, awards, and job titles. But those aren't always the moments that change us. Sometimes it's the phone call that catches you off guard.
The coach you decide to hire
The class you weren't sure you were qualified to teach
The opportunity you almost talked yourself out of
Those seemingly ordinary decisions often become the foundation for extraordinary chapters later. Teaching nearly a thousand students also reinforced a philosophy that's guided almost everything I've done since: understand first. Whether I was helping a manufacturer explain predictive maintenance, coaching a student through a speech, or launching a new product, the best communication always started the same way. Understand the audience before trying to persuade them.
Running fourteen marathons taught me that meaningful progress is built one mile at a time. Marketing taught me how stories influence decisions. Leadership taught me that the best communicators don't just explain what's happening—they help people understand what comes next. What once looked like a collection of unrelated experiences now feels like preparation.
The Real-World Reflection
This summer wasn't the milestone I expected. Like many professionals, I've spent it searching for the right opportunity after being laid off. There have been moments of uncertainty. Moments where I've questioned whether I should be doing something differently.
Something unexpected happened. Without the structure of a full-time job, I finally gave myself permission to build something I'd been talking about for years. I launched my website, I committed to writing Story Behind the Strategy every Monday, Wednesday, and Friday, and I stopped treating public speaking as something I did only in a classroom. I also began building the coaching business that first started as a simple question from a former colleague.
Last year, Shannon reached out asking for help with an upcoming presentation. She knew I had taught Public Speaking and Business Communication for years and wondered if I had ever considered coaching professionals one-on-one. At the time, I had just returned from maternity leave and was balancing a full-time marketing career with life as a new mom.
The timing wasn't right but the question stayed with me. This summer, I finally answered it. One of the first books I picked up while beginning this journey was Brand Yourself for Success by Octavia Goredema. One idea stayed with me: A personal brand isn't something you announce. It's something you build through consistent action. Or as the great Dolly Parton once said, "Find out who you are and do it on purpose."
That realization changed the way I thought about this chapter of my career. I'm not simply looking for my next executive role. I'm building something that can grow alongside it. With intention and purpose that is not dependent on my current job title.
Professor Sherwood's Practical Wisdom
Looking back, I realized something else. Ten years ago, I hired a coach because I wanted to become a better marathon runner. Today, I'm building a business to help other people become better communicators.
The lesson wasn't really about running. It was about recognizing the value of guidance.
For years, I gave those skills away freely to students, coworkers, friends, and former colleagues. I never thought twice about spending an hour helping someone prepare for an important presentation or organize a difficult conversation.
I still love doing that but this summer also challenged me to ask a different question. What happens when people don't just appreciate your expertise—they intentionally invest in it because of the value it creates for them?
That shift in mindset has been surprisingly freeing. The same has been true with voice acting. For years, people complimented my voice. I appreciated it and moved on. This year, I decided to stop wondering "What if?" and start learning from professionals who do this every day.
I'm taking lessons, auditioning. Learning a completely different craft. Will it become another career? I don't know, but at 40, I'm much more interested in exploring possibilities than wondering about them.
So What?
Turning 40 hasn't made me feel like time is running out. It's made me realize how much freedom comes from knowing who you are. I don't feel the same pressure to chase every opportunity anymore.
I want to build things that matter. Teach ideas worth remembering, coach professionals to become more confident communicators, continue exploring voice acting and raise a curious son. I want to leave behind a body of work that helps people communicate more clearly than they could before.
Becoming a mom also changed the way I think about legacy. Success isn't just the title on my business card anymore. It's the example Tobias watches me set every day. I hope he grows up seeing someone who wasn't afraid to keep learning, keep teaching, and keep building—even when the path wasn't perfectly clear.
One other lesson has been quietly taking shape this summer. As I've been building the foundation for my coaching business and self-paced communication course, I've been listening to The Business of Expertise. One idea keeps resurfacing: Experts create value just as much by what they choose not to do as by what they choose to pursue.
That made me think about the last decade. My 30s were defined by saying yes. Yes to teaching, another marathon, to speaking opportunities, to conferences, and to marketing roles that stretched my skills. Looking back, those yeses changed my life. They introduced me to students, colleagues, mentors, and opportunities I never could have planned. I don't regret a single one.
I have a feeling my 40s are going to teach me something different. Not how to say yes. How to say no. No to opportunities that don't align with my values. No to work that drains more energy than it creates. No to chasing titles simply because they sound impressive. No to confusing being busy with making meaningful progress.
The older I get, the more I realize that time isn't my most valuable resource.
Energy is. Where I choose to invest it determines the kind of wife, mother, teacher, marketer, coach, and creator I become. That's a much more meaningful return on investment than simply checking another accomplishment off a list.
Looking back, curiosity has been the thread connecting almost every opportunity I've pursued. Curiosity led me into a classroom, onto marathon courses around the world, learning about the manufacturing industry, stretching my voice acting skills, and now building Story Behind the Strategy. The older I get, the more convinced I become that curiosity isn't a distraction from our careers. It's often what shapes them.
Communication changes lives. If there's one thing I've learned over the last ten years, it's this: The milestones that shape your future rarely feel like milestones when you're living them.
Sometimes they're disguised as a phone call.
A coach.
A classroom.
A marathon.
A website.
My 30s taught me to say yes. I think my 40s will teach me when to say no. For the first time, it doesn't feel like I'm starting over. It feels like everything I've done so far has been preparing me for it. Maybe that's what turning 40 really is. Not the end of one chapter, but finally understanding how all the previous chapters fit together.
