The Art of Letting Go: Why Delegating is Crucial for Entrepreneurs

Here I am, staring at my computer screen, trying to edit a video. I’ve spent far too long struggling with a couple of simple transitions, cursing at the software, and feeling my patience completely disappear. And it’s hitting me: I have no business doing this. Literally.

This isn’t my expertise. I’d like to think I’m a “big picture” person, yet here I am, wrestling with a task that someone else could probably do blindfolded (but shouldn’t!).

Guilty as charged. I’m a micromanager. One of those “If you want something done right, you have to do it yourself” types. Spoiler alert: that mindset doesn’t make you a hero - it makes you the bottleneck in your own business. As entrepreneurs, we wear a lot of hats, but sometimes we forget that we’re supposed to take some of them off and hand them to people who actually know how to wear them.

Delegation is not about shirking responsibility; it’s about recognizing that your time is a finite resource. If you spend hours on tasks that aren’t in your wheelhouse, you’re robbing yourself (and your business) of the opportunity to focus on what you do best. Instead of editing videos, I should be strategizing, building relationships, or creating new opportunities for growth.

Here’s the truth: surrounding yourself with experts in areas where you are not is one of the smartest moves you can make as an entrepreneur. Let the video editor work their magic, the accountant crunch the numbers, and the designer create the visuals. They do their thing, and you get to do yours—what you’re truly an expert at.

Delegation is also a skill, and like any skill, it takes practice. Start small. Hand off one task today and see what happens. Chances are, it’ll come back better and faster than if you did it yourself. Once you see the benefits, you’ll wonder why you ever clung to the “do-it-all” mentality in the first place.

So, here’s my advice to my fellow micromanagers: step away from the editing software, the spreadsheets, or whatever task you’re currently butchering. Trust your team, free up your time, and focus on the big picture. Your business—and your sanity—will thank you.

Yeah, I know, step away from the video editing...

Are you an athlete-turned-entrepreneur or know someone who embodies this journey? Share your stories and insights in the comments!

P.S. I help current and retired athletes successfully prepare for and transition to a new career and business beyond sports with my company, Win Again. I share insights on life after sports, career growth, and powerful networking opportunities. Ring the 🔔 at the top of my profile to stay updated on all my posts—I’d love for you to be a part of the Win Again community!

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30 Seconds with Mark

Take a Moment to Look Back

In the rush to chase our next goal, it’s easy to forget to pause and reflect. But taking a moment to look back at both your successes and failures is one of the most powerful things you can do.

Every win reminds you of your strength, your skills, and the hard work that got you here. Every stumble? It’s a lesson in resilience, adaptability, and growth.

Success and failure aren’t opposites—they’re partners in shaping who you are and where you’re going. When you take the time to reflect, you see just how far you’ve come and how much potential you have to keep moving forward.

So, what have your successes and failures taught you?

Go get 'em!

Be sure to check out the Win Again YouTube channel for more quick tips!

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WIN AGAIN! - The Job Search Playbook

AGAIN! The Job Search Playbook, is filled with over 150 pages of my proven WIN AGAIN methodology, where you’ll discover how to define your true identity outside of being an athlete, plan your path towards an ideal job and business and work towards it.

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You’ve already got an edge!!

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ABOUT ME

Combining my passion for sports and a desire to help others succeed, I founded Win Again, where current and former athletes can discover their identity beyond sports, develop the structure needed to succeed again, and receive the tips, strategies and actionable advice that allows them to WIN AGAIN and be elite in their next great career.

Over the past 20+ years as a business advisor and career coach, I have guided athletes and executives, holding them accountable during their transition.

The Win Again Clubroom events, "Make Your Mark" podcasts, and MYM Live webinars highlight athletes who are making a positive impact post-playing career, and my book “Win Again!” is a job search playbook for athletes, equipping them with strategies needed to land their ideal job or boost their entrepreneurial ventures.

As a graduate of Colgate University and a longtime Manhattan resident with my wife, kids, and Duke, I enjoy playing ice hockey, softball and golf, along with the guitar and piano.

Reach out to me anytime and let me know how I can be of service!

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