Dudley Gets a Side Hustle

Winter arrived in Iowa. Not decorative winter. Not Christmas-card winter, with fluffy snow sitting politely on pine trees while someone drinks cocoa near a window. Iowa winter. The kind where the wind comes across several hundred miles of frozen farmland, finds your house, and begins looking for weaknesses.

It was cold. Unbearably cold. Admiral Byrd cold.

Dudley stood at the back door one morning and looked toward the shed. Somewhere out there were projects. There was a greenhouse to think about, yard work that could theoretically be done, and several things he had confidently announced he would get to “this winter.”

He opened the door. The wind hit him in the face. Dudley closed the door.

The outdoor project season was officially over. There would be indoor projects. Betty had a list. Betty always had a list.

There was painting to do, a few things that needed fixing, some organizing and several projects that had apparently been waiting for Dudley to retire. Dudley was happy to do them.

But sometime around the third consecutive day of temperatures that made leaving the house seem irresponsible, Dudley realized he needed a problem. Not a household problem. He had those. He needed a complicated problem. Something with ambiguity, disagreement, unclear success criteria and at least three systems designed by people who no longer worked there. He missed that.

Dudley did not particularly miss meetings. He did not miss performance reviews, status reports, corporate reorganizations, mandatory training or discovering that an important decision had been made by twelve people on a call he hadn't been invited to.

He definitely did not miss getting up every morning and going to work. But he missed figuring things out. That was different.

So Dudley opened LinkedIn.

If you think Google likes to give you too many answers, try LinkedIn.

LinkedIn had jobs for Dudley. Thousands of them. Senior Director. Vice President. Transformation Leader. Digital Strategy Executive. Technology Program Manager. Chief Something Officer.

Several were marked Perfect Match, which seemed unlikely since Dudley had never heard of the company and had no idea what the job actually did.

He clicked on one. There were 743 applicants. Dudley closed it.

He clicked another. This company wanted a transformational technology executive with twenty years of experience, deep industry expertise, cloud architecture knowledge, artificial intelligence experience, cybersecurity leadership, financial acumen, executive presence and demonstrated success managing global organizations.

The salary range suggested they were hoping to find this person living in their parents' basement.

Dudley closed that one too.

The job market was hard. Real hard. Especially for old guys who would prefer to be retired. There was another problem: Dudley didn't actually want a job.

A job had expectations. A job wanted enthusiasm about the company's exciting journey. A job might eventually want Dudley to attend a leadership offsite.

Dudley had recently escaped. He wasn't ready to be recaptured.

So he stopped looking for a job and started talking to people.

Over the years Dudley had worked with a lot of good people. Some had become friends. Some had moved to other companies. Others had become executives, consultants, vendors or people who knew somebody who knew somebody.

Dudley had kept in touch. Not strategically. He just liked them.

That turned out to be a strategy.

He sent a few messages, had some coffee and took a couple of calls. He told people he was retired but wouldn't mind doing a little consulting if somebody had an interesting problem.

Dudley had rules: no forty-hour weeks disguised as twenty, no rescuing dysfunctional organizations that had spent five years creating the problem and now wanted it fixed by March, and no jobs requiring him to pretend he wanted another career.

He wanted something useful, something interesting and preferably something he could do while it was Admiral Byrd cold outside.

Eventually, somebody had a problem. Then Dudley had a side hustle. It wasn't enormous. It wasn't supposed to be.

A company needed help making sense of a technology initiative. There were competing priorities, too much complexity, plenty of smart people and no shortage of opinions.

Dudley knew this territory.

At first, the old instincts returned. He wanted to understand everything: the architecture, dependencies, operating model, delivery process, organizational structure, risks, metrics and history.

There were diagrams, which Dudley loved.

Then he caught himself.

Dudley had spent years learning how easy it was for smart people to make complicated things more complicated. He had also spent the first months of retirement learning the same lesson about money. Eventually he learned that none of it mattered until he and Betty answered a simpler question.

What do we want our life to look like?

The why came first. The plan came next. The details came later.

So Dudley tried the same thing at work.

“Before we get into all of this,” he said, “what are we actually trying to accomplish?”

There was a pause.

Then somebody answered.

Dudley asked why. They explained.

“What would have to be true for us to call this successful?”

Another pause.

That conversation turned out to be more useful than the diagram.

Dudley started simplifying. He reduced complicated discussions to a few decisions, separated what mattered now from what might matter later and brought people back to the outcome when the conversation wandered into implementation details.

“Why are we doing this?”

“What problem are we solving?”

“What actually matters?”

“What is the simplest thing that gets us there?”

As Dudley simplified things, people started listening.

He had spent much of his career believing credibility came from knowing more. Experience had eventually given him something better.

He knew what could be ignored.

Dudley didn't need to demonstrate that he understood every technical detail in the room. He needed to help everyone else understand which details mattered.

Apparently retirement had improved Dudley professionally.

One afternoon Betty walked past his office while Dudley was on a call.

He had a notebook in front of him. A cup of coffee sat beside the keyboard. Borris was asleep nearby, contributing at roughly the same level he had contributed to the retirement plan.

Dudley was explaining something.

“Let's keep this simple.”

Betty stopped.

She looked into the office.

Dudley saw her.

She smiled.

He knew that smile.

After the call, he found her in the kitchen.

“What?”

“I just heard you tell someone to keep something simple.”

“Yes.”

“And they're paying you?”

“Yes.”

She nodded.

“That's wonderful.”

Dudley waited.

Betty went back to what she was doing.

“That’s it?”

“Pretty much.”

Dudley continued waiting.

Finally she looked at him.

“I've been telling you that for free for years.”

The side hustle turned out to be good for Dudley. The money was nice. Retirement had not suddenly become dependent on it, which made earning it feel different.

There was no ladder to climb and no title he particularly needed. He could do useful work, make some money, help people solve problems and then go downstairs.

More importantly, the work gave his brain somewhere to go during an Iowa winter. He still had indoor projects. Betty still had the list. He still intended to get to all of them.

But a few hours each week, Dudley got to wrestle with something complicated and make it simpler.

For most of his life, Dudley thought expertise meant accumulating answers. Retirement was teaching him something else.

Sometimes expertise is knowing which question to ask first.