Navigating the New Normal of Career Decisions

What do you want to be when you grow up? It’s a question we’re asked from the time we’re in kindergarten. My dad somehow, inexplicably knew he wanted to be a lawyer at that age and never looked back. I was still trying to answer that question into my 30s, even after taking on executive roles in the financial services industry.

For most of us in Gen X and for our Gen Y/Millennial friends, careers have become less a straight line from school to the proverbial “gold watch” and retirement than a twisting, turning road with lots of side streets. We’re not only switching employers and roles within our fields more frequently than our parents, but also jumping off onto other, entirely different career paths in a way that would have been unthinkable for most of our parents.

Our more malleable career paths offer more opportunities for growth and change. Many of us are energized by the prospect of variety, lifelong learning, and the possibility we may have several meaningful, distinct careers by the time we retire (if we do ever retire in the traditional sense.) What challenges so many of us is that because there is often no one single path to follow, we have to be more deliberate in our choices and more conscious of the need to define where we want to go and what we want to achieve. No one else is going to do that for us, but these aren’t waters many of us want to navigate on our own, with no help or validation.

And the financial questions we’re encountering along our journey are far more complex. We’re typically responsible for the bulk of our own retirement savings rather than relying on pensions from an employer for whom we’ve worked for 40 years. Rather than job security, we’re more likely to encounter opportunities to receive compensation in the form of an array of stock option and other equity participation programs. By 2011, the share of private-sector workers covered by defined benefit pension plans had dropped to 18%, whereas the share of private-sector employees owning stock in their employer had increased to 19.5% in 2014.[1],[2]

In my own personal journey, I have found that most of the critical career decisions we face come with financial implications. You may receive a job offer that includes stock options as part of the compensation plan and have no idea how they work or how they should figure into your spending and savings plans. A management role may come with an employment agreement and a lot of new considerations, including severance pay. Or you may be looking to make a change in careers and aren’t sure how these will affect your plans to buy a home or your ability to keep up with your current living expenses.

[1] William J. Wiatrowski “The Last Private Industry Pension Plans: a Visual Essay”, Monthly Labor Review, Bureau of Labor Statistics December 2012 p3

[2] Joseph Blasi and Douglas Kruse, Having a Stake: The Potential of Employee Share Ownership for Workers and Businesses, The Aspen Institute, May 10, 2018


The career decisions we face are challenging because they typically aren’t simple, binary choices. Most of us encounter career inflection points or decisions that have five different aspects that must be understood and addressed to make a committed decision:

  • Strategic: How will this decision affect your career trajectory/is this the right decision for you at this time?
  • Communication: How do you have a difficult conversations with your boss and others, particularly on thorny issues such as compensation and advancement?
  • Financial: What does this decision mean for your financial security and future, and do you feel confident that you understand all of the implications?
  • Lifestyle: Will I be able to maintain the work/life balance I’m aiming for?
  • Family: What does this decision mean for the other people in my life and my ability to support and be there for them?


I started Grow Well Financial Planning to help early- to mid-career professionals better navigate these career inflection points and decisions. By synthesizing the multiple factors that influence your choices and bringing a financial planning discipline to the money-related issues, my goal is to give you greater confidence in your direction so that you can get back to growing your career and living your life.

If you are struggling with a career or major life decision that has significant financial implications, I encourage you to get help. The more people you have in your corner, committed to helping you achieve your goals, the better. These people may include mentors, friends, family, coaches and, of course, a financial planner, but whoever they are be sure to lean on them. No one should have to feel alone with decisions that impact their career, their finances, and their family.

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