There is an old saying, “Do what you love and the money will follow.” Too often, however, people are trapped in a certain lifestyle by the belief that if you make the money, loving your career will follow.

Recently, I was working with an executive client who admitted that while his job was extremely rewarding financially, he was feeling uninspired and trapped.  I asked what would prevent him from making a major change, and he said that he feels locked into his high paying job because he has two homes, an expensive country club membership, two adult children still “on the payroll,” and supports his father’s care.

I posed the question, “What would you do if you won the lottery?”  At that point, the jackpot was over $150 million.  Instantly, his demeanor and energy changed as he excitedly shared that his dream was to open a sailing center where he could rent out boats and offer lessons.   This clearly is a dream that he has given extensive thought to, as he already knew where he would open this business, what the name would be, how he would attract customers, and that he would offer sailing camps to area nonprofits that work with children, such as Big Brother Big Sister and Boys and Girls Clubs.

Let’s be honest: the chance of winning the lottery or finding out that you have some unknown Daddy Warbucks relative who has left it all to you is pretty slim, but his answer and obvious passion made me wonder what others would do.  In an unofficial study (okay, I surveyed friends and colleagues!), the majority reported that if they no longer had to think about money at all, they would travel for a year or two.  Some would return to their current job full-time, as they believe in the company that they work for, and their work is interesting and enjoyable. Others would volunteer, take classes, or join the gig economy by consulting for organizations on a project basis so that they could have greater flexibility over the scope and intensity of their work.   Surprisingly, only two said that they would make relaxation their full-time endeavor!

The other interesting responses from my entirely unscientific study were:

  • I would work, but in a much different way.  I would speak more frankly and have less fear for losing my job based on my actions. I still love what I do.  That’s why I do it.
  • Keep living life as is, until I thought of some way to use that money to start something that makes me happy and benefitted others.  I think people need a purpose, so without working, or a goal, you would spend all the money on “things” to fill that need and run out of the money!
  • Now that I am doing something I actually like, I would keep doing it (this individual left a corporate job of over 12 years recently to run a family business)
  • I would keep working, but I would focus more on the aspects of my jobs that I love and outsource/reduce the things that I do not love.  I would focus on creating.  I would also devote time to the causes I love.
  • I would absolutely “work” but not doing what I do now.  I would start a non-profit focused on something with girls in leadership both in the U.S. and internationally, or write a book about raising our next generation to eliminate the unconscious societal bias.  And, of course, I would do all of this while traveling around the world with my family and friends, drinking delicious wine everywhere!
  • I would work, but would use my skills to help empower underprivileged women to create better lives for themselves and/or donate my time to nonprofits that support things that I am passionate about.
  • I would quit my current job to start a business focused on my hobby (some responses were to open a bakery, a cigar bar, and a dog walking business).
  • I started my own business a few years and love it so much that it feels like I already won the lottery!

In the case of my client, he is not ready to make the leap just yet, so we discussed how to find time to do what he loves while staying in his current role.  We found a sailing center in Boston that offers lessons to disadvantaged children, and he is going to volunteer with them one evening a week, which will give him an opportunity to sail on a regular basis and gain the experience of teaching sailing to children.  He and his wife have decided to start downsizing slowly in hopes of starting his dream business in the next 5-10 years.  At the end of our meeting, we went to the convenience store around the corner to purchase lottery tickets.  Fingers crossed!

If money were no longer an issue, what would you do differently in YOUR career?


Cindy Joyce is the CEO of Pillar Search & HR Consulting. Pillar provides national executive search services for exceptional non-profits and foundations and socially responsible for-profit firms desiring top talent who want an occupassion, not just an occupation.    In addition, Pillar offers human resources consulting services, which was born of clients requesting help on projects beyond executive search, and includes leadership coaching, human resources audits, handbooks, assessing organizational design, training, team building, and employee communications. A woman-owned business, Pillar is based in Boston, MA, and works on both the local and national level. For more information, please visit or email Cindy at