The Inner Journey of Building a Consulting or Coaching Business with J. Kyle Howard

Five years ago, J. Kyle Howard came to me because he couldn't figure out how to package what he did.

He was a former Chief Information Officer with decades of experience across multiple industries, and he knew he had something valuable to offer. He just couldn't articulate it in a way that other people would understand, value, or buy.

So on the surface, it looked like a messaging problem.

It wasn't.

As we worked through the brand positioning and messaging process together, something else began to surface. Questions about identity. Questions about purpose. Questions about who he was apart from the career he had spent decades building. The business-building process became a container for something much deeper than marketing.

Jay is back on Consulting Matters this week as part of my "Where Are They Now?" series, and his story is one I keep thinking about. Not because of where he ended up, though that part is remarkable, but because of what the journey actually looked like.

Why Mid-Career Consultants Often Mistake an Identity Crisis for a Messaging Problem

I've been doing this work for a long time, and one of the patterns I keep seeing is this: people come to me because they think they need help with their positioning, their offers, or their marketing. And sometimes that's true.

But for consultants and coaches who are leaving established careers to build something of their own, the real work is rarely about messaging. It's about becoming. It's about figuring out who you are when the title, the role, and all the external markers of success are no longer defining you.

Jay put it beautifully when we talked. He said that when he finally got the promotion to CIO at a major organization, the day he stepped out of the CEO's office, he realized there wasn't a single person he felt like calling to celebrate. Work had been his costume. His professional identity was intact, but everything else had been quietly starving.

"The work me could leave that personal me at home," he told me. "And I thrived there. But after hours, man."

That is not a messaging problem. That is a much more fundamental question about a life.

The Entrepreneurial Journey as an Inner Journey

One of the things Jay said that I keep coming back to is that the entrepreneurial process has a way of surfacing things you have spent years pushing down. You cannot build something authentic from the outside in. At some point, the inside demands attention.

For Jay, that meant leaving Richmond, Virginia, packing what he could fit in his vehicle, and taking a 33-day drive across the country to San Diego. It meant going through what he describes as a significant personal healing process, including grief he had never fully processed around the loss of his son, and other traumas he had kept buried under decades of professional achievement.

He spent time just being. Sitting on the beach. Letting life slow down. Releasing the need to be anyone for anyone.

"I discovered that no one knew me here," he said. "I didn't have to be anyone for anyone. And I realized, this is what peace is."

I have heard versions of this story many times. The high achiever who leaves the corporate world, not really knowing why, and ends up in a kind of liminal space that looks from the outside like stalling but is actually necessary excavation.

The turning point for Jay came in a hotel lobby in San Diego, where a stranger looked him in the eye and said something that cracked him open. Within fifteen days of that moment, he had two consulting clients and had moved into a high-rise apartment overlooking the Pacific Ocean.

That is not a coincidence. That is what happens when the internal work finally gets done.

The Business That Had Been Waiting 30 Years

Here is the part of Jay's story that I find most compelling from a business standpoint.

The idea he eventually built his company around is not a new idea he discovered during his reinvention. It is a problem he first noticed thirty years ago, on his very first corporate job, and has been observing in every industry and organization he has touched ever since.

At that first job, a petroleum company that had just implemented SAP, he asked a simple question during a meeting: if a customer spends a dollar on gas, how does part of that dollar show up in my paycheck? What he was trying to understand was the connection between what any individual does in an organization and the outcome that customer actually experiences.

No one could answer the question.

And in the decades since, across oil and gas, healthcare, multimedia, mortgage banking, and enterprise technology, Jay kept watching the same thing play out. Talented people working hard inside organizations where no one was connected to the actual customer outcome. Business units operating in silos. Value leaking out of every handoff.

He calls this "value leaks," and he built an entire methodology around diagnosing and fixing them. He named it Opportunity Systems Architecture.

What Opportunity Systems Architecture Actually Solves

Jay's framework starts from a premise that sounds obvious once you hear it but is almost never how organizations actually operate: every person in a business should be able to draw a direct line between what they do every day and the outcome their most important customer is trying to achieve.

He calls that customer the MIP, or Most Important Person. And his argument is that most organizations are built from the inside out, with leadership setting goals and strategies that trickle down unevenly, rather than from the outside in, where the desired outcome of the customer anchors everything else.

When I asked him to explain the difference between a value leak and just an inefficient process, he said something that stuck with me. A process might be technically fine. The leak often lives in the handoff, or in the fact that people have been placed in roles without a clear articulation of the value they are supposed to provide. The process could be perfect and still produce inconsistent results if no one understands how their work connects to anything that matters.

"We just accept the fact that projects overrun or what's delivered is not what was asked for," he said. "But we shouldn't. Because we're just not connected together in a systematic way so that value can flow."

He is currently applying this methodology with the Veterans Affairs department, where an IT shop has been implementing a major platform for eight years without a clear line of sight to how it serves the actual veteran.

Jay is now scaling this work through the Opportunity Systems Institute, with the goal of turning OSA into a licensed, certifiable standard that other practitioners can be trained to deliver.

What Jay Wishes He Had Known Five Years Ago

Near the end of our conversation, I asked Jay what he would tell the version of himself we worked with back in 2020. He gave three pieces of advice that I think apply to a lot of people navigating major professional reinvention.

The first was to not panic. You will not receive everything you need all at once. The clarity comes in pieces, and that is normal.

The second was to stay open and not get defensive when information comes your way. The feedback that stings is often the feedback that matters most.

The third was the most personal. If something hurts, express it. You do not have to do it publicly. But if you need to cry, cry. Let it out. Have the experience.

"Before you can really be successful outside," he said, "the inside has to be available to you."

What I Want You to Take Away from Jay's Story

If you are in the middle of building a consulting or coaching business and feeling stuck, I want you to consider the possibility that the obstacle is not your messaging.

It might not be your niche, your offers, or your LinkedIn presence either.

It might be that the business you are trying to build is not fully yours yet. That there is still some version of who you thought you were supposed to be getting in the way of who you actually are.

Jay's journey took five years, a cross-country move, a name change, a stretch of living in his car, and a breakthrough in a hotel lobby with a stranger. And it landed him exactly where he was always meant to be, working on a problem that has followed him for three decades, finally with the clarity and the language to do something about it.

That is not a failure story. That is a becoming story.

And if you are somewhere in the middle of yours, I hope it gives you permission to keep going.

Next Steps:

• Don't Panic: You won't receive everything you need at once. It's a process, so walk your path without fear.
• Stay Open, Not Defensive: Accept the information that comes to you instead of shutting it down.
• Express What Hurts: If something is painful, let it out. You don't have to do it publicly, but if you need to cry, cry. Have the experience.
• Bring Your Authentic Self Forward: If you need help bringing your authentic identity into the world through a consulting or coaching business, book a discovery call with me or check out my services.

Other articles you may enjoy:

• How to Create a "What I Do" Statement That Impresses Potential Clients [On-Air Coaching with J. Kyle Howard]
• How Denise Musselwhite Went from Fully Booked to Scaling on Her Terms
• Purpose, Alignment, and the Work You're Meant to Do
• How to Overcome the Fear of Failure in Your Consulting or Coaching Business
• How Different Consulting and Coaching Fields Define People-Centered Leadership & Orgs
  
  

About my guest: J. Kyle Howard is an organizational systems strategist and founder of the Opportunity Systems Institute. With over three decades spanning oil and gas, healthcare, media, and enterprise technology, he developed Opportunity Systems Architecture — a methodology for diagnosing why talented people inside broken systems produce inconsistent results. His work has driven outcomes like a 17% to 98% project completion rate improvement and $2.4M in savings. Learn more at opportunitysystemsinstitute.com.

About the host: Betsy Jordyn is a business mentor, brand messaging strategist, and former Disney consultant who helps purpose-driven consultants and coaches build profitable businesses rooted in their unique strengths. With over 20 years in the industry and a knack for turning big ideas into clear positioning, she's your go-to for strategy that aligns with your calling. Work with me: https://www.betsyjordyn.com/services