From Overworked Owner to Strategic Leader: 2 Tons of Bricks

A Heavy Heart

Two Sundays ago hit me like a ton of bricks. Well, like 2 tons of bricks. 

Two different people that we knew died unexpectedly and one far too young.

It was a heavy week, and it just did not feel right to post a blog last Saturday.

In the midst of this, we have had a lot of transitions happening, including multiple family members, all moving within a four month timeframe.

The heavy focus on growing our two companies and serving other businesses has definitely put a toll on everyone at home.

And yet, last Wednesday, here I was standing in front of a small audience talking about how to create freedom in your business and life at an East Portland Chamber of Commerce (Tonya tag) meeting.  

So instead of saying that everything is great and I’m doing fine, I just led with the truth. “It’s been a hard week and frankly, I’ve been working so hard it’s having an impact. So, I don’t want to be throwing rocks out of a glass house, as I make this presentation.”

But what I did say is that I know I have figured out how to move past these challenges in the past. I know I will solve this problem in the future because I’m building a “figurative” oil well. I am willing to put in the current time and effort for the long run. However, I continue to need to remind myself to find more focused time at home. It’s important to walk the talk.

The Presentation

Is This Me? 

It is a simple question, but it forces real clarity. Am I acting as the engine that drives the business forward, or have I become the anchor that slows it down? If my team needed me 30% less each month, what would actually improve, faster decisions, stronger ownership, better execution, and what strategic work would finally get the attention it deserves? Most owners are not short on effort, they are short on focus and time. The real opportunity sits in the gap between where your time goes today and where it creates the most value. Close that gap, and the business starts to move differently.

Where Owners Should Spend Their Time 

• Vision: Set the direction and make it clear enough that your team can act without you in every decision. If you are not defining where the business is going, someone else, or worse, no one, is.

• Key hires: Own the decisions that shape the leadership bench, not just the org chart. The right people multiply your impact; the wrong ones drain it fast.

• Partnerships: Focus on relationships that expand reach, capability, or speed. Strong partnerships unlock growth that you cannot build alone.

• Growth strategy: Decide where to play and how to win, then align resources to that choice. Growth is not more activity, it is focused execution against a clear path.

• Major financial decisions: Stay close to capital allocation, large investments, and risk exposure. Where money goes defines what the business becomes.

• Culture: Set the standard through what you reward, tolerate, and reinforce. Culture forms whether you lead it or not, ownership means being intentional.

• New opportunities: Scan for shifts in the market and act before they become obvious. Your role is to place bets early, not manage what is already working.

Quality of Life is a Business Strategy 

• More family time

• Less stress

• Time to think

• More energy

• Better decisions

• Sustainable growth

Quality of Life is a Business Strategy

This is not just about freeing up your time, it is about increasing the value of your business itself. Most small businesses trade at low multiples because they are too dependent on the owner, which creates risk for any buyer or investor. When you step out of the day-to-day and build a business that runs without you, you reduce that risk and increase the multiple. The work we are talking about is not just operational improvement, it is value creation. As the business becomes more scalable, more predictable, and less dependent on you, it becomes more valuable. And that changes both your quality of life and your financial outcome.

Thank You 

Despite the small crowd, I was grateful for the feedback that I received back from the presentation. 

I always appreciate the opportunity to make a difference, whether speaking in front of 200 people or just a handful of people. I always want to make sure that I’m making a difference for each person who engages in the crowd.

Shout Outs

Great to see my friend and LIghtspeed https://www.linkedin.com/company/lightspeedtek/posts/?feedView=all

CEO, David Solomon https://www.linkedin.com/in/david-solomon-2b30a821/  for breakfast this past week. We had a great run together for nine years and it's great to see him continuing the extraordinary legacy there.

Also, it's fun to connect with a client, Rob Jones https://www.linkedin.com/in/flowcheckllc/ , business owner at Flowcheck, LLC https://flowcheckllc.com/  at my favorite Starbucks. We’ve enjoyed partnering with Rob and his team as they continue building and growing the business.