Fast Checklist for 'Corporate Dropout' Decisions

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Never waste your mid-life crisis. It’s the opportunity you never had - John Higgs.

When I turned 42, I became a corporate dropout to reinvent myself. I was an anomaly in my peer group then, but the midlife career transition is becoming increasingly common in the post-COVID world. A survey by Deloitte found that 47% of employees in the U.S. felt “stuck” or unmotivated at work, while Gallup data revealed that only 35% of Americans are engaged in their jobs.

Here’s a practical guide for evaluating your motivations, strengths, situations, and options for making a ‘Corporate Dropout’ decision.

1. Recognize the Psychology of Midlife Transitions

A significant part of midlife change is psychological. Carl Jung suggested that our personalities naturally shift during middle age, moving us to focus more on personal growth, purpose, and legacy.

This ignites the search for a more meaningful career. But it could be quite elusive if not crafted with care.

Can you find meaning alongside your day job first to test your Why?

Litmus Test - If you can’t quit your weekend leisure activities for what you think is meaningful, you can forget about finding something meaningful once you have dropped out of the corporate world.

2. The Best Selfies You Can Take - Self-Audit > Self-Edit

It’s critical to begin with a self-audit that involves evidence-laced reflection -

• What are my core strengths? 

Think about the skills you’ve developed that come naturally and energize you. Take the Clifton Strenghthfinder test.

• What values do I want to prioritize? 

Is it creativity, autonomy, social impact, or enabling others? Google ‘Values in Action’ is a free survey tool. However, listing your values alone is insufficient; one must force-rank them to make real decisions.

• What are my deal-breakers? 

Understanding what you want to avoid—excessive travel, long hours, alpha energy, or an isolated role—can narrow your options. A negative list is a positive step to avoid the booby traps.

A 2022 study published in ‘Frontiers in Psychology Research' supports the effectiveness of this exercise. Just do it.

3. ‘Futures & Options’ of Different Kinds

Executives in midlife transitions typically find success at the cusp of skills, interest, unfair advantage & demand.

Explore the following paths by ranking the strength of these four filters for each one:

• A new role in the existing company/industry - Why throw the baby with the bathwater? Can you extend yourself to work for a different business unit? e.g., How about reskilling in the areas of corporate interest - ESG, Innovation, Foundation, CVC, etc?

• A new role in a new industry - You can either follow your deep personal interest or identify market trends with a demand gap. For example, List things people reach out to you for or identify high-growth industries, e.g., climate tech.

• Your dream startup - Starting a venture can feel risky, but the Kauffman Foundation suggests that mid-career individuals often have a high success rate. Sign up for a co-pilot program while you are still employed to learn startup essentials, build an MVP, and test the market. This alone can save you hundreds of thousands of dollars in missteps.

• A portfolio career - Consulting allows you to work flexibly while sharing your deep industry expertise. Read “And what do you do?” by Barrie Hopson & Katie Ledger.
  

• Creative pursuits - Today, Everyone can be a media company. Try Beehive or Medium; sharing your knowledge and insights is easier than ever. Someone made $500K with a course on how to take a selfie.

4. The Strength of Weak Ties

HBR research shows that 85% of people find career opportunities through networking, which becomes crucial when transitioning into a new field.

Sociologist Mark Granovetter highlights the power of “weak ties”—people outside your immediate network—to gain broader perspectives on career paths you may not have considered.

I reached out to the second-degree connections. I found them more straight and much more helpful.

5. Small Experiments, Big Insights

Instead of a big leap, start with small experiments to validate your interests. This “test-and-learn” approach aligns with psychologist Herminia Ibarra’s concept of “working identity.” If you are interested in a portfolio consulting career, for example, begin by taking on a side project advising a startup and see the feasibility of such an approach.

6. Treat Your Significant Other as a Board Member :)

Financial stress is a common hurdle for those making mid-career transitions. Calculate what’s feasible given your financial obligations, and set a timeline for when you could comfortably transition. Consider setting aside a “2-year experiment fund”—savings dedicated to exploring new ventures.

And most importantly, present your new life plans A, B & C to your spouse. It’s essential to over-communicate at this time.

A midlife career transition is possible and can be deeply fulfilling. You can design a fruitful path forward with a structured approach grounded in self-reflection, meaningful networks, iterative experimentation, and financial planning.

After all, these are the best times to be alive :) Best Wishes & Happy Diwali!

I teamed up with seasoned founders, investors, and experts to create an ‘Idea to Startup in under 15 weeks’ co-pilot program. It’s for corporate warriors who want to create their venture without leaving their golden nest. This program will help you ideate, build an MVP, validate, launch, and get the tricks of this opaque world of venture capital and innovation economy. Rose-tinted glasses are not enough to survive in the wild. 🙂 

Email me for a 20 minute 1-1 discussion to learn the details > [email protected]

___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.}