The Hidden Trail Markers: What I’ve Learned Supporting Business Owners

Sandy here, sharing my unique perspective as the systems and support person at Doescher Group.

There’s something unique about traveling just behind the leader.

You see the weight they carry. The pressure to navigate every path, read every map, fix every twisted ankle, and somehow still enjoy the view. As the Office Administrator for a company that helps self-made business owners grow, evolve, and exit well on their own terms, I’ve had a behind-the-scenes viewpoint on what it really takes to build a business that can run without you.

It’s not just strategy. It’s not just systems. (Even though those are crucial!) 

It’s a mindset. It's trust. It’s the courage to hand off the compass every once in a while.

When I began my role here at Doescher Group, I never thought I could get so excited about operations, work management tools, or team culture.

As I supported our team as they helped so many owners evolve or exit their businesses on their terms, I came to realize that these “back office” details truly are the difference between businesses that thrive and those that stall out when the trail gets steep.

Here’s what I’ve learned about running a successful business along the way:

The most capable business owners are often the most overwhelmed. They shoulder too much for too long — because they can.

Systems aren’t control. They’re freedom.

• Freedom to step away. 

• Freedom to grow. 

• Freedom to think.

• Freedom to just BE.

The phrase “Things are slipping through the cracks” or “It’s getting away from me a little”  usually signals it’s past time to level up your team or systems. 

Hiring the right support doesn’t slow you down. It unlocks your real pace and potential as a team.

Waiting for the “right moment” to get organized, expand the team, or put systems in place often means you’re already behind. It’s a lot like hiking and realizing you need a raincoat… but it’s already storming, and you’re halfway up the mountain. 

I’ve seen these patterns time and again while supporting our team as they help business owners build companies that can run without them, whether they plan to sell one day or just want to take a long lunch with their family without checking email.

Putting systems and a team in place that they can trust to do great work without them is a game-changer. 

Recommended Read: Management Succession: How are You Doing at Replacing Yourself?

You’ll see me share more thoughts from this vantage point — not as the person at the front of the expedition, but as someone walking close behind, carrying the pack, handing over tools, and seeing clearly what others sometimes miss.

If you’ve ever felt like you were climbing too fast without the right gear, or that your own time and energy is holding your whole business together, I hope what I share helps you feel less alone. And more importantly, gives you something useful for the road ahead.