Navigating Entrepreneurship Later in Life: 5 Tips for Success

Navigating Entrepreneurship Later in Life: 5 Tips for Success

Navigating entrepreneurship later in life holds profound personal significance for me. It’s a journey that resonates on a deep level because I’ve personally experienced the highs and lows of entrepreneurship throughout my career. With the benefit of hindsight, I feel far more capable and confident than I did in my younger days.  And I’m not alone.  Entrepreneurship isn’t just a game for the young anymore.  Would you believe that people aged 55 and up are stepping into the entrepreneurial arena more than those in their 20s and 30s? There’s a growing trend that’s rewriting the rules, and it’s all about starting a business later in life. And these “late bloomers” aren’t just surviving – they’re thriving. It might surprise you to learn that a 60-year-old startup founder is 3x more likely to succeed than their 30-year-old counterpart! 

Why Starting a Business Later in Life Makes Sense

So, what’s driving this trend? Well, it boils down to experience. As the saying goes “With age comes wisdom.”  But it’s more than that. It’s also about the connections we’ve built, the relationships we’ve cultivated, and sometimes, having a bit more financial cushion or, at the very least, a better grasp of our finances. And let’s not forget about the operational and execution skills we’ve honed over the years. The significance of that “been there, done that” mindset cannot be underestimated when it comes to being better prepared for the inevitable curveballs that life throws at us.

The entrepreneurial landscape is undergoing a transformation. Founders over the age of 45 now make up a third of all new entrepreneurial activityAnd here’s an eye-opener:  42% of entrepreneurs over 50 aren’t starting businesses out of necessity; they’re doing it because they’re deeply passionate about their ideas. 

I can personally relate to the desire to embark on an entrepreneurial journey later in life because I’ve walked that path myself.  My entire adult life has been dedicated to entrepreneurship, and along the way, I’ve been fortunate as I’ve accumulated a wealth of knowledge and transformative experiences – some gained through mistakes, while others through successes. In the early stages of my career, I co-founded a marketing agency that exited to a public company. My second venture, a SaaS business that I started in my late 40s, sold faster and more seamlessly than my first.  These experiences, complete with all their struggles and triumphs, eventually led me to establish one of the companies that I run today – Future Proof Advisors. My mission is to help entrepreneurs avoid the pitfalls I once encountered and provide them with shortcuts to get further faster. Launching this venture at a younger age wouldn’t have been feasible simply because I hadn’t amassed the wealth of experiences and established the relationships that now enable us to provide invaluable guidance to our member companies.

So, if you’re contemplating embarking on an entrepreneurial adventure in your later years, here are five practical tips that have not only shaped my path but continue to influence the way I approach the world of business.

Five Tips for Later-in-Life Entrepreneurs 
  1. Prioritize Your Personal Goals: Starting a venture later in life offers a unique opportunity to align your business ambitions with your personal goals. It took me a while to figure this out, but it’s an important lesson. Your company should serve the life you want to lead, not the other way around. Take the time to define your personal objectives, whether they involve achieving financial security, pursuing lifelong passions, or gaining the freedom to do the things you love. Allow these personal goals to inform your business strategy. 
  2. Achieve a Work-Life Balance: As you step into entrepreneurship later in life, finding that elusive work-life balance becomes crucial. Your business demands dedication, but it shouldn’t overshadow the other meaningful aspects of your life. It’s about staying connected with loved ones, nurturing your passions, and, most importantly, taking care of your health and well-being. This balance isn’t just about personal happiness; it’s a secret sauce for long-term business success. In my journey, I realized this balance as my kids grew up, and my parents entered their later years. It struck me how vital it was to be there for them and savor those moments. Plus, with age comes a newfound ability to manage stress, sharpen your focus, and excel at prioritization. Discover the equilibrium that suits you best, enabling you to thrive both personally and professionally.
  3. Embrace Risk, Regardless of Age: Entrepreneurship thrives on innovation and calculated risk-taking. Don’t ever let the number of years you’ve lived hold you back from exploring new horizons. Trust your instincts and be prepared to step out of your comfort zone. Here’s where life’s experiences become your secret weapon. Your journey has likely handed you a treasure chest of wisdom to make informed choices and navigate risks like a seasoned pro. Those who dive into entrepreneurship later in life create substantial economic value by introducing radical innovations capable of disrupting entire industries. Don’t allow your age to undermine your confidence, let it embolden you! Speaking from experience, I co-founded a SaaS business called RSVD in my late 40s. Our mission was to make “waiting in line optional.” What began as a simple idea became a three-year labor of dedication and hard work.  Eventually, RSVD underwent a merger and a profitable exit, becoming RESERVE powered by CLEAR. Today, the service helps travelers breeze past those never-ending airport lines through scheduled appointments. This venture is a testament to the boundless possibilities that entrepreneurship offers, regardless of age. It all comes down to passion, determination, and a willingness to take a leap of faith. 
  4. Stay Tech-Savvy: In today’s digital world, keeping up with technology trends is essential for ensuring your business’s success. While it’s true that as we age, some of the newer tech, like AI, can seem a bit like deciphering hieroglyphics, embracing technology is essential to streamline your operations, engage with customers effectively, and maintain a competitive edge. Remaining “tech-savvy” as a “middle-ager” actually inspired my latest venture. I currently serve as the co-founder and CEO of The Smarter Service, a tech concierge company catering to older adults.  Our mission is to empower individuals at different stages of life, including those actively contributing to the workforce and fellow business owners by equipping them with essential skills and confidence needed to thrive in our ever-changing world. I’ve witnessed firsthand the transformative power of technology, especially for those who embark on new ventures later in life. It’s not uncommon for them to seek guidance in navigating the ever-evolving landscape of innovations and tools, all of which can work wonders for their businesses.
  5. Tap into Your Expertise and Relationships: One of the significant advantages of starting a business later in life is the network and expertise you’ve built over the years. Leverage this valuable asset by seeking advice from mentors, collaborating with like-minded individuals, and using your past experiences to your advantage. Drawing from my own journey, I’ve learned that you don’t have to face every challenge alone. I firmly believe in the adage, “Never try to solve a problem that’s already been solved.” This mantra is what led me to establish Future Proof Advisors, a platform where I could harness the collective wisdom of a network of experts and advisors who’ve “been there, done that.” I’ve come to realize that while I may not have all the answers, there’s always someone out there who does. So, don’t hesitate to tap into this treasure trove of knowledge and connections. Surround yourself with individuals who can help you accelerate your growth, enabling you to achieve exponential success on your entrepreneurial journey.
Embrace Entrepreneurship Later in Life

Embracing entrepreneurship later in life can be incredibly rewarding, both on a personal and professional level. The notion that age should limit your success in the business world is a misconception we must dispel. We’re witnessing a seismic shift in mindset, with more older adults pursuing new opportunities, proving that the entrepreneurial spirit knows no age limit.

So, whether you’re fueled by a long-held passion, the desire to create something new, or simply the pursuit of a fulfilling and balanced life, always remember this: age can be your greatest asset. Your life experiences, the relationships you’ve nurtured, and the wisdom you’ve accumulated along the way are all powerful tools in your entrepreneurial arsenal.

Drawing from my own experiences and as someone who now dedicates their expertise to supporting entrepreneurs and older adults, I can wholeheartedly vouch for the immense potential that entrepreneurship holds at any age. Embrace the opportunities that come your way, prioritize your personal goals, carve out a work-life balance that resonates with you, never shy away from well-calculated risks, stay tech-savvy to harness the power of innovation, and, above all, tap into the wealth of expertise and relationships you’ve cultivated over the years. These guiding principles aren’t just a roadmap; they’re your compass for not only achieving success but also thriving as an entrepreneur later in life.

Here’s to your future success, no matter where you find yourself on life’s remarkable journey!


Have questions or want more entrepreneurial tips? Connect with me on LinkedIn, or drop me an email at Terry@TheSmarterService.com.

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