Re-Designing Your Mid-Life in 2025

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Many people between the ages of 35 and 55 find themselves at a crossroads.

We live years in default mode through subconscious programs that we inadvertently buy from our cultural upbringing, education system, and role models while growing up. The scripts we’ve followed—getting a good job, building a career, raising a family, buying a summer house, or a club membership—may no longer feel as fulfilling.

Some of the chronic symptoms may include feeling increasingly bored, having no delta high with material pleasures, feeling void after socially heavy weekends, etc.

This is not a crisis but an invitation to ‘Re-Design’ your life with fresh purpose and meaning. Grab it and say thanks.

Not everyone has this seed of divine intervention :)

Let’s rely on the discipline of Design Thinking, originally developed to solve complex problems in product design, which can be applied to life.

Drawing from Designing Your Life by Bill Burnett and Dave Evans, the transformative principles of design thinking, and some nuggets of ancient spiritual wisdom, this guide offers a structured approach to crafting a new life that aligns with your evolving identity.

Step 1: Know Thyself. At Least Try!

The journey begins with radical self-awareness. Deeply understand your desires, struggles, and aspirations.

We are all familiar with the workplace gossip and news about the white house shenanigans. How about spending some quality time to understand your feelings, motivations, and the gaps between where you are and where you want to be?

• Conduct a “Good Time Journal,” as Burnett and Evans recommend, tracking moments when you feel most engaged and alive. What brings me energy, and what drains it?

• “Spy on your younger self” remains one of my favorite exercises. Looking back, you will find clues to your true self and see your uncorrupted, non-transactional self engaged naturally with certain activities, people, and areas of interest.

Write daily for a week.

In the ancient Indian scriptures of the Upanishads, self-inquiry (Atma Vichara) is emphasized as a path to understanding one’s true self.

It's good to know what floats your boat.

Step 2: Define the Problem Ghost

You can’t solve the problem you don’t have.

Redesigning your life requires defining the “problem” you’re solving. Is it dissatisfaction with work, a longing for deeper relationships, or a lack of adventure or play?

Use ‘Reframing’ as a vital tool for most situations in life.

Instead of “I’m stuck in a boring job,” reframe it as “How might I infuse more creativity into my work?” This reframing turns obstacles into opportunities.

You might find that seeking meaning is about what you gain and how you contribute to others. True fulfillment often lies in service.

Step 3: Ideate To Generate Possibilities

Don’t limit yourself to one solution. Design thinking thrives on divergent thinking—brainstorming multiple pathways.

We live in a multiverse. But that's a post for another day :)

• For now, use Odyssey Planning from Designing Your Life.

Imagine three alternate five-year life paths:

1. Continue as you are, but optimize for fulfillment.

2. Pivot to a new role, location, or focus.

3. Reinvent yourself completely—an audacious career change or a sabbatical.

• Talk to others who are living your “alternate lives.” These “prototype interview” conversations provide valuable insights without commitment.

Start daily with a personal affirmation, aka Sankalpa (Intention), with your vision, such as “I design my life with joy and purpose.”

Step 4: Start Your Life Lab - Prototype Small Changes

Test small, low-risk changes.

Prototyping is about experimentation without overcommitting. Test ideas quickly and cheaply to see what resonates.

• If you’re exploring a new career, take a short course, freelance, or shadow someone in that field.

• Thinking of moving to a new city? Try living there for a month before making a permanent leap.

The act of “trying” rewires your brain to see possibilities rather than barriers.

Neuroscientist Dr. Andrew Huberman notes that small experiments build confidence by triggering dopamine, the reward chemical.

The Stoics practiced premeditation Malorum, visualizing challenges to prepare for them. It’s pretty quirky, but it's worth diving into.

Step 5: Test, Learn and Iterate - Rinse & Repeat.

Reflect on the outcomes and refine your approach.

Not every experiment will succeed, and that’s okay. Redesigning your life is an iterative process, just like perfecting a product.

• After a prototype, ask: What worked? What didn’t? What did I learn?

• Adjust your approach based on these reflections.

Iteration teaches resilience—every setback is a setup for a comeback.

The Tao Te Ching reminds us to “Be like water”—adaptable and persistent. Each iteration brings us closer to our ideal lives.

Daily Dips - A Non Negotiable

Here’s a simple daily system for implementing your redesign:

1. Reflection Zone (~45 min): Journal the week’s highs, lows, and lessons.

2. Experiment Lab (~60 min): Set one small prototype for the week. Nudge forward.

3. Coffee Connect (~45 min): Engage with mentors, friends, or peers who inspire you.

A Midlife of Possibility - These are the good ‘ol days :)

Redesigning your life at midlife is not about starting over; it’s about starting better.

By applying design principles, embracing spiritual insights, and committing to action, you can create a life that feels intentional, vibrant, and deeply fulfilling.

As the poet Rumi reminds us, “Don’t be satisfied with stories. Unfold your own myth.” The next chapter of your life is yours to design. Make it extraordinary.

^{Image credits - kimiataghavi (pininterest)}

If you want to shift gears in your life, search for a new career, or make an entrepreneurial switch, DM me for a discussion. Happy to help in more ways than one!

___Why is it called /SALTT______________

^{In Roman times, salt was prized as much as gold—it was essential and invaluable and paid as a “salary.” To “earn your salt” is to add real value, which is crucial. The phrase still resonates today, but perhaps with an even deeper meaning. Earning our salt is not about compensation only—it’s about contribution, fulfillment, and the courage to live with intention.}