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The 5 Key Questions to Find Meaningful Work

After 20 years as a career coach, here's what I think you should ask yourself


This past month marked my 20th anniversary as a career coach. Over the years, I’ve seen many changes in the workplace: the growth of the gig economy, an increasingly diverse workforce, and a greater interest in semi-retirement jobs, to name a few. But the one thing that hasn’t changed is people’s interest in finding meaningful work. In both good times and bad, ask someone what matters most in a job (especially someone 50+) and meaning looms large.

So, in honor of my milestone anniversary, I want to share five coaching questions for people eager to find more meaningful work. I hope you find them thought provoking and that they’ll encourage you to discuss them with family and friends:

1. Which five words best describe you?

Understanding who you are and what you value is the critical first step. You need to look inward before seeking solutions outside yourself.

Years ago, as part of the college application process, my daughter’s guidance counselor asked us to describe her using just five words. Initially, it seemed like an easy and fun exercise. But my husband and I quickly learned how difficult it is to come up with the perfect mix of five adjectives as we debated for nearly two hours before reaching consensus.

Describing yourself this way is trickier than you’d think. But it’s a powerful exercise that will help you gain greater clarity about your core values, strengths and gifts.

That’s important, because understanding who you are and what you value is the critical first step in finding meaningful work. You need to look inward before seeking solutions outside yourself. (And as a bonus, this will help you respond with confidence when asked that dreaded, “So tell me about yourself” question in a job interview.)

2. What can’t you stop yourself from doing?

We all have behaviors — both quirky and valuable — that we can’t stop ourselves from doing. For example, a client recently told me she can’t stop herself from mentally restyling people she sees walking down the street. “I don’t do it in a judgmental way,” she explained. “But I can’t help musing about how a different pair of shoes or a shorter hair cut might improve their appearance. I just do it automatically — and it’s fun.”

Does this mean that my client should become a personal stylist? Not necessarily. A career shift involves a multitude of factors, and shouldn’t be based on any single factor. But understanding your natural talents is an important piece of data that always proves useful when evaluating opportunities.

These days, when workers are increasingly expected to handle a wide variety of responsibilities and continually learn new things, it’s keenly important to seek out situations that play to your natural strengths and interests. That way, you’ll still have plenty of energy left over for the more challenging tasks of the job.

3. What would you do if you knew you couldn’t fail?

Career change, by its nature, is scary. As a result, we often avoid pursuing the type of work we really want to do and instead choose the safe path, even if it’s far less satisfying.

That’s why I love this question. It gives you, at least temporarily, permission to suspend your fears and acknowledge your dreams. And when you do, an interesting thing (sometimes) happens: you focus less on failure and more on alternative ways to achieve your goals.

I once asked this question of a client who was an attorney at a powerful law firm. She desperately wanted a better life balance, but was reluctant to give up the perks and status associated with her profession. When I asked her what she’d really like to do, she somewhat sheepishly admitted that she wished she could figure out a way to make a living in real estate, even if people might “think less of her.” Eventually, she worked up her courage and studied for her real estate license. Today, she’s one of the most successful — and happiest — Realtors in our town.

4. What’s one small thing you can do today to move yourself forward?

Changing careers takes work, determination and persistence. There are hundreds of decisions small and large that need to be made. It can feel like an overwhelming process that often results in “analysis paralysis” and stagnation.

But it doesn’t have to be that way.

Even when you’re not fully certain about what’s next, there are always steps you can take to move forward. For example, if you are thinking about shifting into a new field, you can take a relevant class, read an industry e-newsletter or connect with someone over an informational interview.

What most people don’t realize is that passion rarely happens in a vacuum. It builds from action. The truth is, you can’t really know how you feel about an activity until you actually do it.

So even if you can’t yet apply for a job in a different field, figure out a way to take small and consistent steps forward. And if you can’t commit to doing at least one small thing, take that as a warning sign that you haven’t yet found the right direction.

5. If you knew you only had five years left to live, what would you do differently?

While few of us relish thinking about death, this question forces you to zero in on what’s most important in your life: your values, priorities and the legacy you wish to leave.

Not surprisingly, career development books are full of questions similar to this (e.g. “What do you want your obituary to say?” or “What would you do if you had just six months left to live?”). But I prefer this particular question because five years is a long-enough time frame to think beyond the bucket list trips and “time spent with family” that most people say they’d choose if given just a few months to live.

Yes, the question is macabre. But the good news is you’re still very much alive. So use this exercise as motivation to make the changes you need in order to create a more meaningful life today. And hopefully for many, many more years to come.

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