In 2013 I hatched an idea for a software system to deeply analyze over-the-road trucking dispatching for optimum load selection and scheduling. In a two-week bleary-eyed marathon of coding I created a working prototype. Exhausted, and satisfied that it worked, I set it aside.

In 2014 I was looking for investment opportunities and I decided that trucking software was one of the best I had laying around. I spent a good portion of the 2014 year-end holiday season turning the prototype into a usable beta version. I intended to put a truck on the road to use as a research and development “guinea pig” for the system.

Around that time I landed my book Investing With Purpose in a publishing contract. With much reluctance, I put trucking aside for another eight months. I poured myself into writing the best darn book I had in me. In August I turned it in.

Then I went into motion. I hired an experienced trucking business manager, and we began filing all the paperwork required to operate as a common carrier. I worked on the software between other responsibilities, and the pieces started coming together. Unfortunately the manager I hired didn’t work out in the role, and I terminated her employment. We were mid-project, and I decided to carry it forward with the help of my assistant.

The Truck

And we did. We completed the paperwork, bought a truck, hired a driver, and got the thing rolling. I scrambled to adapt the software to the needs of the business on the fly. My system worked as I hoped it would. It was a thrill to see this two-year-old vision come into being.

At the same time I began to realize my system just didn’t fit the way the people of the trucking industry actually work. Several people had warned me in advance about dishonesty, unreliability, and rule-breaking in the trucking industry. They were right. Information flow from brokers about loads, rates, and schedules was limited and inaccurate (or even falsified). I also discovered that harsh verbal pushing and shoving were standard practice whenever a problem or sticky situation arose with a booking or delivery.

Not only is my software incompatible with that environment, I am incompatible with that environment. On several levels.

When all of that started to come clear, I had to grapple with disappointment and a sense of failure. My big dreams for that software were changing to nothing but big problems. I had never “struck out” on a business endeavor before, which meant my perfect batting average was going up in smoke. I imagined peeling our shiny new logo off the truck. I didn’t like it.

Continuing longer wasn’t going to make anything better. I made the call and pulled the plug. I called my driver and told him we were shutting down. We filed paperwork to end a business. I’d never done that before.

The same day I made the call, I started to think about what I want to swing the bat at in 2016. I had (irrationally) feared I would never find interesting new possibilities to replace that passion project. I was surprised how quickly ending one thing made room for creative thoughts of the future.

Since my batting average will never be a thousand again I guess I can let that go. Maybe there’s even a little relief in that. I feel surprisingly un-devastated.

I think the lessons learned from this excursion were worth the time and money they cost me. Here are a few of them:

• It’s really hard to swim against the current of culture. Behaviors, values, and worldviews engrained for decades (even generations) can overpower individuals, innovations, even economic forces.
• Corruption is a real thing. I knew that conceptually. Now I know it experientially. I like to think the best of people. Reality isn’t that simple.
• Engineering a solution that works does not guarantee a business that succeeds. I’m going to keep this lesson close at hand in my future angel investments. Yes, the product or service must function as envisioned. It also must be accepted and paid for by people. It’s probably more important to understand the worldview and patterns of behavior of those people than to understand the engineering of the product itself.
• Starting small really is a good idea. I had considered buying an entire trucking business to develop my software alongside. I’m glad I stuck to my belief in lean startups and minimum viable product.
• Sometimes cautionary tales are true, and there’s still value in finding out for yourself. There’s always someone who says “that won’t work”. In this case they were right. In most other cases in my career, they were wrong. Trial and error is a good way to tell which is which.
• The attempting process is valuable in itself. Success at the original objective is not the only reason to attempt something. I like success better than failure. At the same time, the process of attempting to manifest something brings much learning, and awareness of new opportunities. I’ll remember lessons learned for the rest of my life, and I could list at least a dozen business ideas that this trucking venture sparked for me.
• Trust the abundance of the unseen future. There will be new to replace what you let go of. New ideas, new relationships, new projects, new inspirations. Accepting (even causing) the end of one thing is a good way to make space to discover what’s next.

P.S. Anybody wanna buy a truck? :-)

Every week I hear from one or two people who found value in my blog post. I’m really grateful for the chance to share my thoughts and experiences and help a few others in the process.

At the same time, the truth is the reach of my blog is small. It hasn’t caught on, gone viral, or anything of the sort. Alas, mega-blogger I am not. When I evaluate the return on investment (impact per hour of my time), it doesn’t make the top list of most impactful things I do.

In my book I preach ROI. I advise the reader to focus resources where the greatest returns are. It’s time for me to practice that. My foci in coming months will be the book, the Leadership Development Cohort, Sunstone Transportation, the acoustical products business, and the a/v rentals business.

I’ll probably post a few times per year, maybe more someday down the line. Thanks for reading. Over and out for now.

It was a quiet moment between me and the FAA examiner. He was a veteran pilot, and much older than I. The airplane I was flying was pointed back toward Champaign, the airport we had taken off from almost 2 hours earlier. My voice sounded strained and shaky as I made the routine radio calls to Champaign approach. I was sweating from the heat, and from the stress.

The check ride I was on is the last step in getting a private pilot’s license. It was a Saturday, and my only chance to take the check ride in time to carry out my plans to travel for this project. I had just performed a range of maneuvers — steep turns, s-turns, lost procedures, navigation by map and compass, simulated engine failure, short-field landing, etc.

The first half of the ride went great — some of my best flying to date. Then I made some small mistakes on my short-field landing, and some big mistakes on my soft-field takeoff. It was ugly and I knew it. A few minutes later I got flustered when he asked me to combine an unexpected maneuver with my simulated engine failure procedure. I forgot some steps and missed my planned landing area. By that time any feeling that this was going well was gone, and a sinking feeling of failure was setting into my gut.

Once all the required maneuvers were done, the examiner gave me a second chance at the engine failure procedure. I knew it was make or break. I was hot, exhausted, and out of adrenaline. I didn’t see a field that looked good. I turned left to look behind me, and I didn’t like my choices there either. I said to myself “Get it together or you are going to fail this test RIGHT NOW.” I made a choice, but it wasn’t a good one. I barely cleared a couple of obstacles on the way to it. The sinking feeling was increasing.

After that second chance on the engine failure, we headed back to Champaign. So there we sat, in quiet except my radio calls. The test was harder than I expected. I was pretty sure I had failed. I was exhausted and discouraged.

In the noisy silence of engine rev and radio static, I was surprised to feel the examiner’s hand rest on my shoulder for just a few seconds. It was as if he was saying, take a breath, it’s ok. Relax and finish this. I didn’t expect that from the man judging my performance against the standards.

I landed gracefully at Champaign, parked, and shut down the airplane. As the propeller sputtered to a stop, I flipped off all the switches and waited to hear the worst. Instead I heard, “Congratulations. Meet me inside.” I was pretty sure that meant I passed, but I didn’t quite believe it until he handed me my temporary pilot’s license.

As I drove away from the airport, I remembered that moment and his hand on my shoulder. Celebration would have made sense, but tears rolled down my face as I steered my car toward home. Working toward my license over the past year was harder than I ever thought it would be. The final check ride stretched me to my limits. And this quiet old man who could have failed me showed me kindness. He helped me do a hard thing, and it moved me deeply.

We all need a hand on the shoulder sometimes, and we all have a chance to be that for others when they get shaky. Moments like these bring a whole lot of meaning into life and leadership.

What does it feel like to work here?

What does it feel like to be a customer there?

What does it feel like to spend time with you?

Everyone needs to feel competent, included, and cared about. If someone or something makes us feel stupid, left out, or rejected, we will avoid it like the plague. These are the real reasons employees quit and customers go elsewhere.

A good paycheck or a good price are not enough to overcome a bad feeling. Pay attention to what it feels like for them.

Relationships work best when you respond to what the other asks for and ask for what you need.

It might be easier for you to say “let me help you” than to say “I need this from you”. Perhaps one feels generous and strong, and the other selfish and vulnerable. Great relators do both.

Your co-workers, your friends, and your family members need to know you’re human like they are. They need to know how to please you. They need you to participate in a two-way street of give and take with them. And you need the connection and the energy that come from asking for what you need and receiving it.

Clear asking makes things better.