I spent three days with my 15 year-old niece exploring her college ambitions. Four ahas emerged.  1) I’m glad I’m not a sophomore in high school these days. 2) What a difference asking the right questions can make. 3) How unexamined mind-habits can have powerful, lasting (and unintended) consequences; and 4) how outside perspectives can change everything.

It’s a complex and competitive world whether you are 15 thinking about college or 55 and musing about retirement. When I was in high school my cohort didn’t really think about college decisions until late junior year when we faced taking an S.A.T. exam. Most of us looked at the local state or community college as the ‘given’ because in 1960’s California, in-state college was nearly free.  You only needed scholarships and financial aid if you were thinking of Stanford or an eastern Ivy League school.

Planning for college today begins much, much earlier. The tasks are daunting and the questions endless: what courses are needed in high school? What is the right balance of academics, activities, community service? What paperwork is required by when? Should you pay for test preparation services and special college advisors? What is the best-fit college? Which have the most financial aid?

Similarly, when our parents thought about retirement they expected to quit working (as in, “that’s the end of all that!”) at around 65 and could count on 66% of their income needs coming from pensions and social security. Today less than 34% of income will come from Social Security and pensions[i]. That means planning and saving needs to start 30 to 35 years in advance of retirement! And today’s seniors expect to be actively involved post-retirement. Only 14% believe retirement is “my time to rest.”[ii]

Planning for college and retirement today are two of the biggest stressor in people’s lives.

Asking a Different Question

One of the biggest insights I had from my time with my young visitor was how important asking the right questions is. You can ask two kinds of questions. One narrows our thinking, often producing an ordinary but faster answer; another promotes a wider exploration of information and produces more possibilities, but tests our patience.

The first kind of question sounds like:

  • What do you want to major in? What school do you think you will go to?
  • When do you want to retire?

The second sounds like:

  • What do you imagine your career to be like? If there were no constraints what kind of school would WOW you?
  • What does retirement mean to you and what do you hope it will be like?

Most of us ask the first kind of question and get the ordinary answers, for example: “Well I like math so I think that I might be a math major and maybe a math teacher.” I guess I will go to the local community college since it will be easier for my parents to pay for it.”

When our young student was asked the second type of question, however, you could see her mind expand along with her enthusiasm, curiosity, and desire to learn more about the possibilities.

It’s no different for facing the end of our careers. Asking a narrow question, like “What are your plans for retirement?” often produces, “I just don’t know what I will do with myself.” Asking exploratory questions can produce amazing insights into where energy lays, or what really matters and motivates.

Inspiration comes with great questions.

Mind-Habits and New Perspectives

Mind-habits are when we think automatically without really thinking or without reflection on our assumptions and biases. The impact of those habits is powerful.

We all have mind-habits. Families advising students have biases from their own past experiences; counselors have biases based on what they’ve seen before and assume will be true this time too; or assume that their information about a student is complete or sufficient to define the answers.

As a senior in high school, my counselor saw me as the popular cheerleader from a divorced family with a high B average, ‘tracked’ out of honors classes. He advised me not to pursue top tier colleges. “You’ll likely be a strong C student if you do.” His cognitive biases could not see options that might support my eventual PhD and a successful consulting business.

Owners have mind-habits about selling and retiring from their businesses. They overestimate the value of their company and refuse to believe new information based on sound valuation methods. Or they believe no one else can run their business and so fail to delegate or prepare prospective internal buyers. Or, an owner knows of two friends who were sorry they sold their company, therefore, he or she shouldn’t sell either. Such cognitive biases can be self-fulfilling.

Outside perspectives are powerful at awakening, if not exploding, mind-habits and biases. They help us see the larger picture or system at work when we have been drilling down on too many specifics. They help us give up looking for the perfect answer and consider possible experiments to learn from first.

Sometimes those outside perspectives are an intervention by caring others: a peer, relative or mentor who confronts assumptions with information or arouses aspirations by spending time posing different questions or visiting possible future scenarios (a college campus, a volunteer organization.)

Sometimes it takes a paid professional who can provide new information, ask the uncensored questions friends can’t, or introduce new frameworks for trying on new futures.

What If…

For anyone facing end-of-career decisions, what if you thought of yourself as that 15 year old looking ahead to college. What different questions would you want to be answering about your future?  What questions would open your thinking and challenge your mind-habits? Whose outside perspectives would help you to gain information you don’t even know you need and to see multiple options beyond the ordinary?

Ask Yourself:  What might be transformative for your future?

iRoger Ibbotson , et al,  Lifetime Financial Wealth Management GIC, Morgan Stanley as of 2007

ii Anne Tergesen,  “For Second Careers, A Leap of Faith”, Wall Street Journal, May  17, 2013.

Photo Credits,  Deposit Photos