Five years ago, J. Kyle Howard hired me because he was struggling to articulate what he did and how to package it into a business.
At the time, he was a former CIO trying to figure out how to turn decades of experience into something other people would understand, value, and buy.
In other words, he thought he had a messaging problem.
What neither of us realized was that the challenge wasn't really about messaging.
As we worked together, something deeper began to emerge.
Questions about identity.
Questions about who he was apart from the career he had spent years building.
This week, as part of my "Where Are They Now?" series on Consulting Matters, J. Kyle returns to the podcast to reflect on what happened next.
And what a journey it has been.
Over the past five years, he tried on different business ideas, moved across the country, went through a significant personal healing journey, and ultimately found his way back to an idea that had been trying to get his attention for more than 30 years.
What I love about this conversation is that it captures something I've observed throughout my career.
People often come to me because they think they need help with positioning, messaging, offers, or marketing.
But for many consultants and coaches, particularly those leaving established careers to build something of their own, the real journey isn't about marketing.
It's about discovering who you are when the title, the role, the organization, and all the external markers of success are no longer defining you.
It's about finding the courage to build a business that reflects who you actually are, rather than who you think you're supposed to be.
J. Kyle's story is a powerful reminder that clarity doesn't always arrive in a straight line.
Sometimes the detours are part of the path.
Where to dive in:
00:00 — Entrepreneurship forces inner work
02:09 — What Jay really needed in 2020 wasn't a business plan
06:01 — The promotion that should have been everything
17:33 — Choosing himself over the Northrop Grumman job
18:58 — The hotel lobby stranger who cracked him open
21:20 — 15 days later: two clients and a 35th floor view
23:16 — The question that had bothered him for 30 years
30:11 — What the business actually is in plain English
37:44 — How Jay accidentally became an OD consultant
40:52 — Live messaging coaching on air
50:21 — Three things Jay would tell his 2020 self
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 explore my services.Other episodes you may enjoy:
What it Really Means To Be On-Purpose (Ep166)
Are We Aligned on What People-Centered Leadership and Organizations Really Mean? (Ep164)
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
