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Career Clarity
February 25, 2026
You hit 50, and fewer career opportunities come your way.
You are not alone. This is normal. Boom! Didn’t think I was going to call this confusion ‘normal’. Let me break this down for you.
First off: You are going ot be fine. You will figure this out. You have all the experience in the world. You are well educated. You are intelligent (probably too intelligent). You have friends and a support network. You have industry relationships. You have witnesses to your past success. You are not going to run out of financial resources. And of course, you’ll find your next move that puts money in your pocket. But you can do this the long way (the way you have been doing it forever—waiting for a phone call) or the fast way (using my method for strategic clarity).
In 2018, when I dropped out of corporate America, I didn’t quite know what would be next for me. All I had was a personal commitment to freedom without burnout. I was convinced the money would come eventually, and as a side product of pursuing my passion for tech innovation.
But to bring clarity to all of this, I had to be methodical. I didn’t want to waste my time with countless networking calls, hoping something would stick. Here is what I did instead:
First, I had to go all the way back to my childhood and decipher the life code that makes me the person I have always been. It’s the programming we receive between birth and 10 years that shapes how we perceive the world and how we make decisions. This programming can never be changed. It is the underlying code for all our decisions in life.
I did this by writing down in detail the things I love doing, the things I like doing, the things I’m good at doing, the things I don’t like to do, and the things I really hate doing. You might think this is easy to do. But right there, most people fail.
Many produce a list that reads like a résumé, and they are too focused on always positioning themselves for the next job opportunity. So I had to learn to trust that it is OK to be selfish and to truly think about what’s meaningful to me personally. When I was done with my list, I realized that 80% of it had absolutely nothing to do with what I have been doing in my career all along.
After that, I marked a handful of entries from the list with a yellow highlighter to indicate that those specific things give me energy. I also had a read marker to highlight those specific things that drain me of all the energy. This data point is important thereafter.
Then, I analyzed that data to produce a passion statement. It sounded something like this: “I am passionate about sharing my experience with others.” This was groundbreaking, and it took me quite some time to bring it down to something so simple and ultra-focused that it can not be misinterpreted.
When I first started the process, I had things like “I am passionate about technology and product innovation in the space of artificial intelligence to improve the business bottom line.” Or, “I’m passionate about executive leadership development to help others level up in their career.” The same point here as in the previous section, most people naturally lead with their résumé and with the next opportunity in mind. They are not selfish enough to bring it down to the most fundamental components of themselves. This is very hard, and without a coach, I would not have been able to accomplish this. Thanks, Jane!
The third step was to craft my positioning statement. The formula I used for that is very simple and comes from the marketing world. It looks something like:
FOR: my client, WHO: faces this challenge, MY NAME: delivers this value, UNLIKE: the competition.
For example, one of my early positioning statements read like this: FOR aspiring tech leaders WHO are unclear how to make it to the C-suite, DR OLIVER DEGNAN provides a proven playbook from the trenches of the C-suite you can use to level up in the next 15 months (or less), UNLIKE a traditional coach with an unaccredited coaching certification who never leveled up anyone to the C-suite.
Today, my position statement is much stronger, with a spin designed to induce a sense of urgency in the observer and force a quick close. It’s one of those tricks I’ve learned from people like Jeffrey Minor and Chris Do. You should look them up on YouTube.
I give you one example: FOR professionals who lose $88,000 yearly by not getting that C-suite promotion, DR OLIVER DEGNAN puts a playbook in your hands to jump to the C-suite in the next 6-9 months, UNLIKE countless pieces of advice on LinkedIn and YouTube that cost you time and energy.
I’m hoping you are beginning to get it.
After my positioning statement, it was time to develop my professional brand. A brand is how others see me. I needed to have full control over that perception.
I underwent a transformation from positioning myself in a way that I thought others would like to perceive me to positioning myself in a way that promotes my passion.
It is that particular part that has helped me to bring absolute clarity to all the things I thought I could and should do, and ultimately narrow it down to only two things that I’m doing today: Business and Career Advising.
Notice I didn’t say ‘coaching’. For me, advising is about actively solving problems. Versus traditional coaching that often just seems to result in a friendly self-realization session to overcome self-inflicted challenges. OK, that is a bit harsh on my part. And I’m not trying to dizz coaches here — it’s my poor attempt at saying that’s just too boring for me. I must build something — a product or a person.
Eventually, everything I started doing on my own was perfectly positioned to align with my passion, and those activities give me back more energy. By the way, this is also one of those things that help me never experience burnout again.
In a nutshell, my passion is helping others do awesome things without burnout. It’s simple and elegant. And yes, it took me quite some time to make it this simple. I challenge you to produce something simpler.
And my goal in life? My goal is to get 100 million out of burnout before the day I die.
My goal used to be something in the neighborhood of “My goal is to build the most reliable healthcare products with artificial intelligence to save patients’ lives.” You see it now? What a bunch of blah blah blah to lead with my resume to attract the next job opportunity. Plus, it sounds like I was brainwashed. What the heck did I mean by ‘saving patients’ lives’? I’m not a medical healer.
There you have it. The formula for strategic clarity.
It’s not rocket science. But it is a process that will take you time to trust that it is safe for you to just be yourself. Stop faking it. Stop pretending. Stop pleasing others all the time. Stop positioning yourself to fill others’ shortcomings. Begin to be selfish. And begin to trust that you already have everything within you to experience success beyond your wildest dreams. And most importantly, you already know how to experience freedom. You just have to remember it.
Cheers!
Oliver
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