Lifestyle Design: Should We Take It More Seriously?

A New Era of Midlife

For decades, life was imagined as a straightforward path—study, work, retire. Any concept of lifestyle design seemed unnecessary, if not outright indulgent, or something of a woo-woo concept.

But this outdated linear map no longer applies. Advances in medicine and shifts in culture mean many of us now have several extra decades of productive, fulfilling life to look forward to—productive, fulfilling decades.

At the same time, the traditional school-career-retirement model that we may be so used to is dissolving fast. These days, it's not unusual to be juggling multiple careers, taking a midlife sabbatical, or pursuing a completely different path, well into your 60s and beyond.

If you're in midlife and looking to stay active, professionally engaged, and purposeful for the long run, then lifestyle design is no longer optional—it’s essential.

Why Such a Big Deal?

For much of the 20th century, life followed a rigid formula. You went to school, pursued a career, and retired—hopefully in time to enjoy what remained of your golden years. Under these conditions, the concept of lifestyle design wasn’t urgent. Your roadmap was pre-written; you just needed to follow it.

Fast forward to today, and that trajectory has completely unraveled. Here’s why lifestyle design has emerged as a crucial framework for modern midlife.

Longer Lifespans, Greater Potential

Even if you don't, you should live and plan your life as if you will live into your 90s.

The prospect of additional decades amplifies your potential for reinvention, creativity, work, travel, and meaningful new chapters.

Nonlinear Careers & Roles

The notion of a single lifelong career is gone. People are increasingly pivoting to new industries in midlife, launching businesses, taking breaks, or layering caregiving responsibilities with a portfolio of work arrangements.

This fluidity demands intentional design rather than defaulting to the old question: “What's next?”

Blurring Boundaries

Traditional work-life divisions no longer exist. Today, many in midlife are simultaneously parents, entrepreneurs, creators, travelers, and caregivers.

Without a fixed path or timeline, lifestyle design helps you focus on what truly matters—whether that’s health, purpose, relationships, or creative work.

The Rise of the Nonlinear Midlife

Gone are the days of retiring at 65 and fading into the background. Today, midlife is all about redesigning how we live, work, and contribute in often fluid, creative, and nontraditional ways.

Here are some real-life examples of nonlinear midlife paths:

Redesigning Work in Midlife

• Transition from a corporate job to a portfolio career–combine consulting, coaching, content creation, and community building
• Earn a certification in fields like design, AI, or coaching at 52, paving the way for a flexible, purpose-driven career.
• Build a personal brand around your expertise, monetizing your knowledge through coaching, consulting, or public speaking.
• Scale back to a 3-day workweek to prioritize health, relationships, and a passion project for your next chapter.

Expanding Your Financial Flexibility

• Diversify your income with real estate investments, advisory roles, and creative projects to achieve financial independence.
• Become a hybrid entrepreneur–balance a part-time job for financial security while pursuing a startup or passion projects.

A Life of Travel and Freedom

• Take a sabbatical to travel slowly, living in a new country every few months while building an online business.
• Ditch the traditional 9-to-5 office routine to work as a digital nomad, sharing your expertise from anywhere in the world.
• Spend half a year volunteering or working remotely to test a new location before committing to a permanent move.
• Explore creative pursuits while traveling, combining adventure with monetized hobbies like filmmaking, digital art, or public speaking.

Creativity or Passion Project

• Start a podcast or write a book at 60, turning your decades of expertise into both financial and creative fulfillment.
• Head back to school in your 50s or 60s, studying something completely different purely for the love of learning.
• Start a nonprofit or impact-driven initiative that lets you give back while maintaining control over your schedule.

The Five Principles of Lifestyle Design

All these shifts underscore the need for lifestyle design. It’s no longer about following a single “recipe” for success. Instead, it’s about intentionally shaping a life that evolves–in line with the world around you, as well as your strengths, assets, passions, and changing priorities.

1. Longevity

Plan as if you'll live well into your 90s. Even if you don’t, this mindset encourages healthy habits, financial security, and long-term purpose. Treat age 80 as the new “midlife,” ensuring there's enough gas in the tank—physically, financially, and emotionally—to enjoy these bonus decades.

2. Nonlinearity

Flexibility is the name of the game. Careers now ebb and flow, personal commitments shift, and the traditional retirement blueprint is obsolete. By embracing this zigzagging path, you free yourself from rigid societal expectations and remain open to unexpected but rewarding opportunities.

3. Reconfiguration, Not Reinvention

We're all familiar with the notion of "reinvention," particularly in midlife, when we often associate it with doing a complete "reset" in the midst of some kind of emotional "crisis."

Reinvention in midlife isn’t about starting over; it’s about evolving. You already have the tools—skills, relationships, assets like health, and knowledge. Instead of resetting, focus on reorganizing these elements to create a life that aligns with your next chapter.

4. Diversification

Don’t put all your eggs in one basket. Diversifying your skills, networks, and revenue streams can insulate you against life’s uncertainties. This principle applies to work, creativity, and even friendships.

5. Valuing Time

Each moment becomes precious in midlife. Reassess how you spend your time—on the wrong projects, draining relationships, or needless distractions. Being deliberate with your time allows you to move closer to a meaningful, intentional life.

What Lifestyle Design Makes Possible

The beauty of lifestyle design lies in its ability to align your life with today’s realities. Here’s why it’s more important now than ever.

No Built-In Blueprint

Don't follow somebody else's roadmap. You're unique, and there's no guarantee it will work for you. Design your own roadmap.

Freedom to Pivot

Once you cast aside the shackles of age-related thinking, it's tremendously liberating. You can launch a business at 60, enroll in school at 70, or shift between full-time and part-time work seamlessly. The possibilities are endless.

Blend Work, Life, and Health

Many midlifers blend paid work with rewarding personal pursuits fueled by wellness practices and thoughtful schedules. There are unlimited combinations.

Continuous Growth

Pick up new skills, or combine old skills with new ones in unique ways to make you stand out and stay curious and relevant.

Entrepreneurial Fulfillment

These days, you don't need to raise millions and become the next Silicon Valley unicorn. Thousands of people are forging careers for themselves as successful independent creators, with very low entry costs. You can too.

Practical Steps to Start Designing Your Next Chapter

Lifestyle design is no longer a once-in-a-lifetime exercise. It's ongoing and you need to be intentional about it. Here are practical steps to get started:

Audit Your Life

What energizes you daily? What drains you? What aspects of your life can you remove? Make an honest inventory.

Define Your Ideal Lifestyle

Most of us fall into the trap of working hard and then enjoying the fruits of our labor once we have the financial resources. But as we all know, things rarely pan out the way we expect.

It's a lot more practical to imagine your ideal lifestyle first and then work backward from there towards achieving it.

Take Small Bets

Test out new work, hobbies, entrepreneurial or social media projects with minimal risk.

Build a Support Network

If you're thinking of staying active and engaged for the next few years, you'll need to pick a virtual network of advisors. Avoid the temptation to pick people from your age group. Find people who have trodden the path you are now on, and learn from them.

Carry Out Regular Reviews

Life changes—update your plan at least once every three to six months to stay aligned. Be brutal with your time and ditch any pursuits that are not leading to fruition.

Shape the Nonlinear Midlife You’ve Always Dreamed Of

Midlife isn’t a crossroads; it’s a continuum. As traditional paths towards retirement become obsolete, lifestyle design is an essential tool for thriving and staying relevant.

It’s up to you now. Design your path. Build flexibility. Prioritize passion, purpose, and values.