Managing Yourself - 6 Questions to Ask at the Midpoint of Your Career

by Rebecca Knight

Summary.   It’s common to wrestle with feelings of unmet expectations, missed opportunities, and paths not taken when you reach the midpoint of your career. But experts say that arriving at middle-age is also a profound opportunity for growth and self-reflection. It’s a chance to...more

Reaching middle age — which often coincides with the midpoint of your career — can be a moment when your achievements, ambitions, and reality collide. Wrestling with feelings of unmet expectations is common; realizing that many of your early dreams and aspirations might not happen — like ever — is sobering. 

But experts say this period also offers a profound opportunity for growth. It’s a chance to reevaluate your priorities, draw from your experiences, and carve out a path that aligns with your goals for the future. 

The first half of life is about “accumulating,” says Chip Conley, founder of the Modern Elder Academy and author of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age. “Do this! Try this! Accumulate friends, children, resume items, and stuff for your house,” he says. “The second half of life is meant for editing. It’s when you discern what’s truly important to you.”

Embarking on this “editing” process might seem overwhelming, even impossible, amid the busyness of midlife. The demands of work, home, and other commitments can leave little room for introspection. But finding the time and mental space to look back on your career and reassess is worthwhile, says Ebony Joyce, founder of Next Level Career Services, which provides coaching for mid-level professionals. “It gives you perspective to chart the shape and direction of your future,” she says.

Here are six questions that Conley and Joyce suggest asking as you take stock of your career in midlife.

1. What will I regret not having done or learned 10 years from now? 

Regret may have a negative connotation, but it can be a powerful teacher, says Conley. “The benefit of getting older is that you have peripheral vision and you can see the future,” he says. “You understand the consequences of your actions.” Conley recommends harnessing the power of anticipated regret, which involves imagining the disappointment you might feel in the future if you don’t take certain actions today. This foresight can help you make decisions that your future self will appreciate, he says. 

Research suggests that maintaining curiosity, learning new skills, and embracing new experiences are correlated with living a longer, happier life. Conley, for instance, learned to surf and speak Spanish in his own midlife. So, consider subjects you’d like to learn about, routines you’d like to take up, experiences you’d like to dive into, and places you’d like to go now, before it’s too late. The goal, he says, is to “make decisions toward long-term fulfillment, not immediate gratification.”

2. How do I tap into my purpose?

Many people are influenced by external factors early in their careers, whether it’s parental pressure, societal norms, or a desire to conform to particular notions of success. This can lead to career choices that prioritize others’ expectations over your own desires and interests. Later, sacrifices for spouses and children may further eclipse personal ambitions.

As you reach the midpoint of your life, Joyce says that it’s time to shift from a career shaped by external forces and others’ agendas to one driven by what you want and find meaningful. “It’s an opportunity to break free from coulda, shoulda, woulda and focus on your dreams,” she says. 

Determining what a personally meaningful career might look like for you requires self-reflection, says Conley. “What excites you? What agitates you? What are you curious about? What activities from earlier in your life did you once enjoy but have since neglected?” The answers can help you identify potential pivots in your career, whether it’s moving to an adjacent industry or transitioning to something entirely different. “It helps you see you have more options available.”

3. What mastery or gift have I developed that I can offer to the world? 

By midlife, you’ve gained a trove of experiences, insights, and perhaps a few hard-earned battle scars along the way. You can reflect on the skills and know-how you’ve acquired and consider how you might use them to make a positive impact on others, says Conley. He draws inspiration from the psychiatrist and author David Viscott, who said: “The purpose of life is to discover your gift. The work of life is to develop it. The meaning of life is to give your gift away.” 

Conley recommends a classic exercise associated with Peter Drucker. This involves someone asking you “What business are you in?” five times in a row, with each successive question helping you to refine and focus your response. “The final answer often yields an epiphany,” says Conley. “That’s how I realized that I’m a social alchemist who brings people together.” The aim is to come away with a clearer understanding of your strengths and how they can be applied in ways that are meaningful and consistent with your personal purpose.

4. What do I want my days to look like? 

We’re often encouraged to think big about our professional lives, says Joyce. Bosses and career counselors ask you to envision your future in five or 10 years, or to define your idea of success. While these prompts can be valuable, Joyce suggests contemplating your future by thinking smaller. “Get to the micro level by considering what you want the details of your daily routines to look like,” she says.

Rather than focusing on grand long-term goals, Joyce recommends envisioning a typical day in your ideal future. Consider how you want to spend your time, who you want to interact with, and what you want to do outside of work. This thought experiment allows you to gain clarity about the life you want to create and align your goals with the practicalities of your day-to-day existence.

5. What trade-offs am I willing to make — or no longer willing to make? 

It’s natural to second-guess your choices and mull over potential what ifs. Maybe you’d have more money if you’d done things differently. Perhaps you’d have closer relationships or a stronger marriage if you’d made other decisions. 

But Joyce says you must bear in mind that “you made choices that made sense for your needs and priorities at the time.” Now that you’re older and have more perspective, those may have evolved. Perhaps your children are out of the house or more independent, allowing you to focus more on your career without the distractions of household responsibilities. Alternatively, you may no longer be willing to make the sacrifices you once did; instead, you want your personal life to take precedence.

The key, she says, is to give careful consideration to your values and priorities, and to make conscious decisions about the compromises you’re willing to make. “There are no right or wrong answers, but you need to be intentional,” she says.

6. What’s getting better about my life? 

Faltering memory, creaking joints, hot flashes, fading energy levels — the challenges and indignities associated with getting older are all too familiar. But rather than dwell on them, Conley suggests shifting your mindset to appreciating the upsides of aging: the wisdom you’ve gained, the experiences you’ve had, and the personal growth you’ve achieved. This change in perspective isn’t just pie-in-the-sky optimism; it can have real, tangible benefits for your well-being and longevity. One study showed that people with positive self-perceptions of aging lived an average of 7.5 years longer, on average, than those with a negative outlook.

Ageism persists in both the workplace and society, but Conley says you need to confront your own internalized ageism, as well. “If you show up with curiosity and passionate engagement, people will notice your energy, not your wrinkles.”

. . .

Middle age brings with it a host of transitions and challenges: empty-nestingmenopause, loss of parents, unexpected health issues, and changes in careers and relationships. There’s no roadmap. The goal, says Conley, is to draw on the wisdom and experiences you’ve gained along the way, and “consciously curate the next phase of your life.”

Rebecca Knight is a journalist who writes about all things related to the changing nature of careers and the workplace. Her essays and reported stories have been featured in The Boston Globe, Business Insider, The New York Times, BBC, and The Christian Science Monitor. She was shortlisted as a Reuters Institute Fellow at Oxford University in 2023. Earlier in her career, she spent a decade as an editor and reporter at the Financial Times in New York, London, and Boston.

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