By Jill Allemang, Jallé Consulting
In conversation with Andrew Kris on Borderless Executive Live
Most careers wander more than they climb, and my conversation with executive turned consultant Jill Allemang was a good reminder that change does not have to feel like a leap. Jill works with people who are mid or late career and wondering what comes next. Her view is simple, career renewal is a process you can navigate, not a crisis you have to survive.
She breaks it into three phases. First, do you actually need a change. Second, how do you change. Third, how do you stay with it long enough for something real to take shape. Many of us rush straight to the middle and make the journey harder than it needs to be. Jill starts by helping people sort what they already know about their choices and values. Most of us have more clarity than we think, it is just hidden under day to day noise, fear, or assumptions we have never tested. Beginning with what works often brings a sense of relief and creates early momentum.
Jill’s method is personal but practical. Small group sessions give people space to reflect without pressure. You work with your own confidential material first, then choose what to share. It reduces the isolation that often comes with career uncertainty, and it protects privacy when the subject feels close to the bone. The tone changes as a result. You stand on your experience as an adult who has made plenty of good decisions already.
We also spoke about how mid and late career have shifted. Ten to fifteen years in, people begin to ask if their work still feels meaningful. Twenty or thirty years in, the questions narrow around relevance, longevity, and what life looks like beyond the traditional retirement script. Longer lives and evolving finances mean many of us have another chapter ahead, not the end of the story. Two things help, staying connected to peers who operate at your level and keeping your curiosity alive. Jill is direct on this point. Pick one piece of technology that interests you and learn it until it becomes second nature. It is a simple, effective way to stay confident and current.
The most creative stage of any transition is the middle one, when you have stepped away from something but not yet stepped into the next role. It feels uncomfortable, but it opens room to experiment. Try a small project, take a short course, shadow someone doing work you admire. The aim is not a big bet but useful data. If something energizes you, you will invest effort. When you invest effort, your skill grows. When your skill grows, the market notices. This steady flywheel beats endless analysis and brings decisions back to lived experience.
Sticking with change is the final hurdle. It always takes longer than we would like, and the mix of fear, past disappointments, and advice from sceptical friends can slow progress. Naming these pressures helps. So does setting timelines that match reality and drawing some boundaries. A trusted sounding board, whether a coach, mentor, or peer group, keeps you moving when motivation dips. Underneath it all sits one simple truth. You get one life, and staying in work that dulls you rarely serves anyone.
If any of this strikes a chord, watch the podcast on Borderless Executive Live, or listen on your preferred app.
Talk to Jill Allemang directly at jallemang@jalle.com.
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