Strategy and the Seasons of our Life
Jul 28, 2026
One of the most common mistakes in business - and in life - is assuming that one successful strategy will work forever.
In 2018 I met an author, Martin Reeves, who explored this idea in an outstanding book, Your Strategy Needs a Strategy. Martin helped me immensely think through how best to drive change in my organization at the time. His central premise was refreshingly simple: there is no single "best" strategy. The right approach depends entirely on the environment you are facing. A strategy that succeeds in one situation can fail miserably in another.
Martin described several distinct strategic approaches. Sometimes your objective is to optimize and steadily improve an established business. Sometimes you must adapt rapidly to an unpredictable environment. Sometimes you must create a market that doesn't yet exist. Other times, success depends on building an ecosystem where many people win together. And when circumstances become severe, survival itself becomes the strategy until strength can be rebuilt.
Business leaders instinctively understand this. I believe life deserves the same wisdom.
There are seasons when we are climbing a mountain. The goal is clear, the path is steep, and progress comes from discipline, persistence, and endurance.
Other seasons require us to cross a river. There is no marked trail. The current changes. We cannot simply push harder - we must read the water, adjust our footing, and sometimes change our route altogether.
There are times when we are building something entirely new: a career, a marriage, a business, or a family. These seasons reward courage more than certainty.
Other times, we are protecting what we've spent decades creating. Our strategy shifts from rapid growth to stewardship, from proving ourselves to developing others.
Still other seasons call for renewal. Health challenges. Career setbacks. Financial hardship. Personal loss.
When life becomes harsh, the goal is no longer maximizing performance. It is preserving hope, rebuilding strength, and preparing for the next chapter. Sometimes simply getting through today is an extraordinary strategic accomplishment.
The mistake is believing we should attack every season with the same playbook.
Many professionals continue trying to "outwork" problems that require learning. Others keep planning when they should be experimenting. Some continue competing when they should be collaborating. Others cling to stability when their future requires reinvention.
Wisdom is not having one great strategy. Wisdom is recognizing when your strategy no longer fits the landscape.
The older I become, the more I appreciate that life asks different things of us at different times. In our twenties, we often need to build capabilities. In mid-career, we must learn to lead people rather than simply produce results. Later in life, our greatest contribution may not be what we accomplish ourselves, but what we enable in others.
Each season calls for a different version of us.
Perhaps that's why the most fulfilled people rarely become prisoners of their past successes. They remain curious. They continue learning. They adapt without abandoning their values. Their purpose remains steady, even while their methods evolve.
That may be the greatest strategic lesson of all. Your values should be remarkably consistent. Your strategy should not.
Questions to Consider:
- What season of life are you in today?
- Is your current strategy matched to the reality you face - or to the reality you wish still existed?
- What should you continue doing because it still serves you well?
- What strategy has outlived its usefulness?
- If you embraced the needs of this season, rather than resisting them, what might become possible?
Tony Thelen is the founder of The River Coaching and Consulting, LLC, an executive coaching firm based in West Okoboji. He is the author of "Am I Doing This Right?" and "Things We Desire." He works with CEOs, business owners, executives to remove pain, anxiety, and stress while making room for true personal and professional growth. Contact Tony at [email protected] or learn more at www.therivercoach.org