“I imagined myself… 80 years old… and I felt this deep sense of regret if I don’t try this.”
Lord of The Rings fans may recall that the full title of The Hobbit was The Hobbit, or There and Back Again.
Many will say “you can’t go back again”, particularly to an earlier stage in their career. This isn’t always true.
Like me, my friend Dave Miller started out as an actuary, became a consultant, and then opened a successful coaching practice. His practice was particularly focused on business and sales, which often led to career coaching, and we collaborated on many occasions, doing workshops together at Actuarial Clubs and Society of Actuaries conferences. This built our visibility and reputations, while gaining clients (including a multi-year corporate gig).
Where our paths diverged was when, after two decades of coaching, Dave decided he wanted to go back to actuarial work, though naturally with a strong focus on leadership development.
This presented a unique challenge:
- How could he get employers to see him as a viable candidate for something that had not been his focus for over two decades?
- And would they accept a ‘return’ to actuarial work as making sense – why would he want to go back to what they might perceive as an earlier stage in his career?
Complicating his search was the rise of COVID, and all of the disruption that created in the job market.
While I can’t claim a lot of credit for Dave’s successful transition, I did help him with messaging and particularly interview preparation – how to answer some of the tough questions and shift the employer’s focus from the perceived flaws above to the assets he brought to the table.
In the end, not only did he find a great actuarial position where the company truly valued him for his coaching skills, but that company considered him for multiple possibilities, and ultimately selected him to lead the most technical unit of those, despite the fact that it was the one where he might have the maximum level of ‘rust’.
So how did Dave make that successful transition?
I interviewed Dave for my Career Journey series, and you can watch the recording here.
Some key points:
On Dave’s transition from Actuary to Coach
Over time, Dave found increasing disconnect between his job and his personal desires.
- His work was technical and analytical.
- Outside of work, everything was relational and people-oriented—church, life, and relationships.
- This led him to say, “I think I want to do something different.”
He applied the “rocking chair regret” test as a decision tool.
He imagined himself at 80 years old, in a rocking chair, thinking back:
“How would I feel if I didn’t try? I felt deep regret.
That told me I should try. If it didn’t work, I’d go back.”
On Building His Coaching Practice
If you start a business, the big question is: How do I get customers/clients?
You can do it yourself, hire someone, or have a mechanism that funnels clients. Marketing and selling is often the hardest piece.
The key is perseverance.
Starting a business brings every insecurity out, and you have to face them.
It’s tough but rewarding. You need to focus, don’t quit, and have an entrepreneurial spirit. A great idea helps too.
The cost can be stress and sleep. Boundaries are important because your business is always on your mind.
The reward is doing what you love, having control over your schedule, and flexibility. I was tired of working for certain “yahoos.” In your own gig, you set your culture. All of the upside (and downside) is yours alone.
On Dave’s Transition From There To Back Again
“A consulting assignment doing change management/training had me on-site three days a week for 19 months. That brought me back into corporate life, and I realized I missed it—getting to know people over time, seeing things through.
“There were two drivers:
- I got tired of always developing business;
- and I missed collaboration and working with a team.
“But it was hard getting back in: people looked at my resume and didn’t know what to do with me after being gone two decades.
…
“The biggest challenge was presenting myself so people “got it.” Ultimately, you have to be true to yourself. I worried my technical skills were weakest and I boned up on software and did interview prep — then they didn’t ask a single technical question across six rounds.
“The other challenge: the mental game—discouragement. Hope matters. Faith helped me interpret setbacks as “not the right one.”
The key is to prepare, not perform:
- Be authentic and still prepare.
- Don’t give answers you think they want to hear.
- Show how your experience translates.
- If they want vanilla, fine—but if they want something different for better results, they need you.
There was so much more to our conversation. For all the details, watch the recording. And let me know what you think – leave a comment!
Enjoyed your blog post. Lots of things in your blog resonated with me. The biggest takeaway is to ” not give answers you think they want to hear – be yourself. If they don’t want you, then their loss! 🙂
Thanks for commenting, Patricia! I’m glad that resonated with you.
No one ever said “I wish I’d worked harder” on their death bed.
So true, Kandas.