Life's Wake-Up Calls: Career Moves in Uncertain Times

I ask myself three questions when making career changes.

Life's Wake-Up Calls: Career Moves in Uncertain Times

When we're reminded of death, we often start reflecting on our life choices. That was perhaps why, recently, when I attended a young friend's funeral and mourned their sudden loss, many of our mutual friends came to me with questions about making important life changes. Likewise, as the year-end approaches, more and more people have come to ask how to think about making a significant and often risky career decision. 

Most of them are my former team members, people in their mid-twenties who work in corporate or tech jobs. They wondered if they should leave their well-paying jobs for ones that might be more fulfilling but offer less money. These other jobs could be at smaller companies, non-profits, or starting their own businesses.

When I was leading large organizations, I often had people come to my office asking similar questions. Lately, I’ve been focused on mentoring entrepreneurs, so it wasn’t until this tragic incident that the questions returned to my attention. 

Over the years, I have learned that instead of answering those questions by articulating my own life choices, it’s more effective to ask them questions that help them make their own decisions. 

1. How did your upbringing affect your dreams and career expectations?

Parents often like to think they know more and can shape their children’s lives based on their own experiences. But when my wife and I had twins, we realized that in addition to upbringing, genetics also played a big role in shaping each individual’s character and preferences. 

The same goes for making career decisions because everyone was raised in a different family environment and has genetically different preferences.

Reading one of the business biographies written by Walter Isaacson, or anyone else makes for fun reading but a poor way to get career advice. Your family and theirs are likely quite different. 

 Research has shown that your childhood has the largest  impact on your job choices. While parents assume that their direct career advice may be influential, they may be unaware that they can also exert a strong career influence simply by serving as examples in their jobs. 

The first step is to ask yourself which part of your parent’s advice or influence resonates with you. But then think deeper about how you are different from your parents. A good rule of thumb is who you looked up to that were not your parents. 

My father is a civil servant, proud to have dedicated his entire career to public service. Growing up, I was always more interested in talking to his friends who were entrepreneurs. But that desire for impact, as most of the startups I am involved in have some public service component. 

This book by Jacobsen has a quote that sums this up: "If your family's values mesh with your own, you can find strength and guidance in them throughout your career; however, if these values don't mesh, you'll build a career that your parents take pride in, but that leaves you frustrated and empty" 

2. What risks can you take now?

Risk is an important question because of the increasing volatility of what was once considered stable corporate jobs. The technology bubble has burst yet again, so salaries in this sector are dropping particularly fast.  Roles with less than five years of experience are experiencing the largest declines.  

So, it’s important to calculate how much monthly income you can actually afford to give up. I suggest they create a monthly budget and see where they can cut expenses. If they're single or both partners in a marriage are working and don't have kids to support, they can often afford a bigger pay cut than they think. For families with kids and or aging parents to support, understandably, things may be trickier, but this exercise is the same.

Then, instead of just comparing their current salary to the new job's pay, they should look at what similar jobs pay at local companies. Look at total salary, not just in terms of cash. For example, you might want to consider reducing cash for stock in a startup. In traditional local companies, benefits could extend to daily expenses like housing.

3. Why do you need to make this move now? Why not later?

One common misconception when making drastic career changes is that they need to do it swiftly. It's now or never.

One such change is going from corporate to entrepreneurship. I made this change; perhaps that's why many seek my advice. But what seemed to most people like a drastic change was a slow, gradual process. I worked part-time at, which was newly formed then, before jumping to join full-time a year later. I even went back to consulting again before eventually starting my own startup. 

Here’s me in Aceh after making the jump from consulting to the non-profit startup Kiva to hunt for microfinance banks around Southeast Asia. After a couple of years of this nomadic lifestyle, I jumped back to consulting for a brief period.

One common mistake people make when thinking about big career changes is feeling rushed. Many successful entrepreneurs didn't start their companies until they were in their forties or later, even though the media often focuses on young startup founders like Mark Zuckerberg or Bill Gates.

Research has shown that the average successful founder is around 45 years old. Eric Yuan of Zoom, David Baszucki of Roblox, and ​​Bob Parsons are just a few examples of founders who had rich careers before starting up. 

So, my usual advice to the ones who come to me and want to jump into entrepreneurship is to consider a transitional phase, such as moving to a smaller company or joining part-time. This approach offers a dual advantage: maintaining a steady income while acquiring diverse skills essential for founding a successful company.

For those inclined towards public service, the advice differs. If the opportunity involves working with a trusted public leader is time sensitive, I recommend immediate action before that leader gets replaced.

A memorable instance was when a former team member contemplated joining the Ministry of Health’s Digital Transformation office to contribute to the COVID-19 response. Given the critical timing of the pandemic and the Ministry's political mandate, I advised that it was a 'now or never' situation. He could always return to the private sector later. This decision led to several rewarding years for him in public service before his recent transition back to the private sector.


I remember going through these three questions myself a few years ago when my grandmother was on her deathbed.  I remember sitting next to her and thinking about which decision I would regret more later in life. Not long after my grandmother passed away, I left my leadership role to focus on mentorship and investing

There is no right or wrong answer to the three questions above. You can have an impactful and rewarding career in corporations, government, or entrepreneurship.  What’s important is that you make a decision and move on.