Why Designing Your Future Shouldn’t Wait for

When we think about preparing for the future, “retirement planning” often comes to mind - pensions, savings, and maybe dreams of a quiet life by the sea. But there’s a deeper, more powerful kind of preparation we often overlook: designing a future that energises and fulfils us, not just when we retire, but starting right now.
A decade-old article from Harvard Business Review, titled “Design a Retirement That Excites You”, remains uncannily relevant today. While it focuses on retirement, its core ideas go far beyond that phase of life. It’s really about how to navigate change with intention, creativity, and a design mindset—approaches that are invaluable for anyone rethinking their career, making transitions, or looking ahead with curiosity.

The authors—former Stanford professors and founders of the life design movement—argue that we should stop thinking of the future as something that starts after work. Instead, we should design our futures the same way a designer develops a great product: by prototyping, testing options, and aligning decisions with our personal values and aspirations.

At Sideminds, this philosophy is at the heart of what we do. We help experienced professionals—particularly senior executives and leaders - gain clarity about their next steps, whether they’re looking for a full career pivot, exploring a portfolio career, or preparing to leave a traditional role behind.

Our career strategy work guides clients to understand what they really want out of the next chapter of their working life—and how to make it happen. For many, that includes portfolio career planning, which means creating a blend of work that might involve consulting, board roles, writing, teaching, volunteering, or entrepreneurship. It’s a powerful and flexible model for anyone who doesn’t want “retirement” to mean the end of purpose, impact, or income.

The HBR article is a helpful reminder that future planning isn’t about waiting for the right time - it’s about starting now, with tools and strategies that work. And with the right guidance, the process can be not only effective, but energising.

At Sideminds, we believe your next chapter should be the one that fits you best - thoughtfully designed, courageously shaped, and confidently lived.

Read the full HBR article here.

About the Author

Gareth Helm

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