Today, I want to speak directly to business owners in the trades: Are you in a position to hang up your boots?
This question emerged during a recent coaching call with a client I’ve worked with for over seven years. Every session, we kick things off with a “WIFFLE” — What I Feel Like Expressing. This time, my client, Jonathan, shared a surprising thought:
“I don’t feel like I’m working hard enough. The company is doing well, but I feel like I should be doing more.”
Jonathan’s frustration stemmed from a sense of guilt — a common feeling among business owners who have transitioned from the grind of daily operations to strategic leadership. Let me explain why this shift is actually a sign of success, not stagnation.
From Worker to Leader: The Journey
When Jonathan and I started working together, he was hands-on in every sense. Seven years ago, he was manning trucks, climbing trees, cutting branches, and running the entire team. Today, his role looks entirely different:
- He and his brother crafted a clear vision, mission, and core values for their company, aligning their team around these principles.
- They became intentional about the team culture—hiring employees who represent their brand and have the right qualifications.
- Divisional managers now run the day-to-day operations of individual divisions and companies.
- Systems have been implemented to review team performance, set goals, and outline areas for growth.
- Weekly team meetings and regular one-on-ones ensure alignment and accountability.
- They host company-wide sessions to educate, challenge, and inspire their employees.
As a result, Jonathan no longer needs to be in the trenches. He spends more time with his family, enjoys vacations, and embraces his role as a leader. This shift has allowed his business to work for him, rather than the other way around.
The Entrepreneur’s Dream
Many entrepreneurs start their journey by grinding—working long hours, wearing multiple hats, and putting in the hard labor to get their business off the ground. Over time, through intentional systems, leadership, and consistent growth, the business evolves.
But when things begin to feel “easy,” it’s natural to question whether you’re doing enough. Here’s the truth:
If you’ve created a self-sustaining business where the team does the work, and you’re free to focus on strategy, you’ve achieved what every entrepreneur dreams of.
Retire Your Work Boots
For those in the trades, this journey symbolizes a rite of passage: the moment you can retire your work boots. Imagine placing those boots in a glass box as a testament to the hard work, resilience, and leadership it took to build your business.
Here’s how you can get there:
- Define a vision, mission, and core values.
- Build a culture that attracts and retains the right team.
- Develop systems for accountability and growth.
- Transition from doing the work to leading those who do it.
- Keep learning and challenging yourself and your team.
When you’ve put all these elements in place, you’ll have the freedom to spend more time with your family, pursue personal passions, and live life on your terms.
Let’s Make It Happen
Your business is a stepping stone—a vehicle to help you achieve your dreams, whether that’s building wealth, enjoying more time with loved ones, or eventually selling your company for a profit.
If you’re not quite ready to retire your boots and want guidance on how to get there, I’d love to be your guide. Let’s work together to create a plan for success.
COACH MICHAEL DILL is an Award-Winning Certified Business Coach, global speaker, and published author. He is a proud Action Coach Franchise partner as well as the President of Power & Ice Wealth Creation a strategic leadership company that works with business owners, leaders, teams, and entrepreneurs to both develop a systematized and structured organization while accelerating their mindset, efficiencies, and effectiveness to grow both personally and professionally to achieve extraordinary results. He brings more than 40 years of business and entrepreneurial experience in his leadership, team training, and mentoring practice. Businesscoachmichaeldill.com