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Entrepreneurs are notorious for postponing joy, myself included, sometimes. We say, “I’ll take that trip after I close this deal,” or “Once I retire, I’ll slow down and spend more time with my family.” But what if “later” never comes?
Last Thanksgiving, my family and I were in Auckland, sailing on an America’s Cup boat. We met this super-friendly couple who had just barely retired. They were on cloud nine and shared with us their plans to hop over to Hawaii and then keep traveling. My wife and I recommended they get the same tour guide we’d used, someone who’d shown us the best adventures on the islands.
A few weeks later, we got a text from the wife saying her husband had passed away from a massive heart attack right after they returned home, just before Christmas. She thanked us so much for recommending our Hawaiian adventure tour guide because those adventures became their last fun experience together before he passed.
Talk about a gut punch! I haven’t been able to stop thinking about it. It reminded me that tomorrow isn’t guaranteed, so why in the world do we keep delaying the moments that make life worth living?
Start living now
Life doesn’t come stamped with a “Best Enjoyed By” date. Just like that retired couple in New Zealand who were so full of life and plans, we entrepreneurs always look toward the horizon. We thrive on the challenge of pushing limits and taking calculated risks — it’s in our DNA. But ironically, many often dodge the biggest risk of living in the moment.
Now, if that couple’s story doesn’t make you stop and think about your own life, I don’t know what will. We all fall into the trap of thinking that we have all the time in the world to travel once we retire, relax and create moments with our loved ones. But life has a funny way of throwing curveballs. Before you know it, the kids are off on their own adventures, your body isn’t as young as it used to be, and you realize you’ve put off the things that truly matter. “Someday” isn’t actually a time to plan for.
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Give your all in everything you do
I have five kids, and I run multiple businesses, so I get the juggling act. Most entrepreneurs feel like they’re constantly spinning plates, thinking, “If I give more to my career, I’m shortchanging my family; when I’m with my family, I’m dropping the ball at work.” Here’s the thing: balance is a myth if you’re defining it as a clean 50-50 split.
Be fully invested in whatever you’re doing. I show up 100% at work and dive in with focus and creativity. When I’m at home, I’m all there — closed laptop, silenced notifications, hoops shot in the driveway and talking about life around the dinner table. You can accomplish more (and do it better) when your mind isn’t split between guilt and responsibility. It’s not about clocking hours; you need to be fully present and invested wherever you are, whatever you do.
Success means nothing if you lose what matters most
I’ve worked with entrepreneurs who’ve built billion-dollar businesses but ended up with broken marriages and kids they barely know. I’m sorry, but that’s not success in my book. I don’t care how great your net worth looks if you can’t point to any genuine relationships. Nobody aims to neglect their family — but this stuff happens when you live a completely imbalanced life, solely focused on money and status.
In fact, you’re going to be a whole lot more creative, calm and receptive to fresh opportunities if you’re not constantly fighting battles at home or carrying a load of guilt for working. When I know my wife and kids are solidly in my corner, it frees me up to chase new ventures without feeling like I’m shortchanging the people who matter most. That kind of support lifts a massive weight off my shoulders.
Build a life you don’t need a vacation from
Like you, I’m a Type-A achiever, and many out there will relate when I say focusing on the next milestone is more invigorating than pausing to celebrate wins. But think about this: if we never pause to appreciate the moments that matter, we’re missing out on the true payoff of all our hard work.
Celebrating isn’t just for ourselves alone. Share the ride with your family so they feel like they’re part of it. If you closed a big deal this week, take a moment to pause and do something fun with your spouse or kids — a night out at your favorite restaurant, a weekend hike, or a movie night.
Ultimately, if you’re building a life that you can’t wait to escape from or you only get to spend real quality time with your family during a vacation, something’s definitely off. I always encourage my clients to imagine a life so fulfilling and integrated that they don’t need to think about taking time off. Sure, travel is awesome, but the real key is creating everyday joy that makes your home life just as rewarding as any exotic destination or any dream deal.
Related: When You Are Ready to Become an Entrepreneur, Do These 5 Things
Finding meaning beyond success
Entrepreneurship is incredible. We get to innovate, solve problems, dream big and push boundaries. But if we lose sight of the people we love and abandon our family and friends, what’s the point? The couple we met in Auckland had a beautiful glimpse of retirement adventures, and I’m thankful they at least experienced Hawaii. Yet it’s heartbreaking that it ended so quickly.
Don’t keep kicking the can down the road, assuming you’ll enjoy life “later.” You always have the chance to start now. Say yes to those big business goals, but don’t push back the chance to go on adventures while you’re healthy and your kids still want to hang out with you.
