How To Build A Career (And A Life) That Won't End In Regret

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“The only thing I’ve ever failed at is retirement,” lamented a former CEO from a multi-national apparel company. At 57 years old, my former client was facing the hard reality that he wasn’t prepared for life outside his job. That’s because he’d never built a life outside his job.
That’s the paradox Karen Dillon, along with co-authors Clayton Christensen and James Allworth, addresses in How Will You Measure Your Life. She discovered that too many people build successful careers, reach uncommon pinnacles, only to discover how unhappy and unfulfilled they are. She, Christensen and colleagues also have another book just out, Competing Against Luck.

Karen herself had a similar experience. By all accounts, she had reached the peak of journalism achievement, becoming the editor of the Harvard Business Review. Then, she did what most rising stars would never consider. She resigned. Says Dillon, “I loved the job, but loved my life and family more. I was in my mid 40s and I knew I was going down the path of not leading the life I wanted to live. I needed to course-correct before I was backed into a corner.”

Most early-career professionals obsess over the next stop on the train. They want the prized assignment that will accelerate their earning potential, get them promoted, and shine on their resume. Says Dillon, “It’s a very exciting time. It’s hard to think about the end of the line. The incremental tolls you pay along the way are hard to notice. You forget someone’s birthday that matters. You cancel plans with people you want to spend time with. Though hard to detect, those small choices start adding up.”

But as was the case with my client, don’t wait until the end of your career to figure out what would have lead to a genuinely fulfilling life. Plan for fulfillment now. Dillon warns, “You can’t decide to build a great career, and then get on with being a great parent and reconnect with your college friends. Life doesn’t work that way.”

Here are five important practices to adopt early in your career to ensure you finish fulfilled. And if you’re already past “early,” adopt them now. It’s never too late. Though a difficult leap of faith, you must trust that choices you make for the longer term won’t jeopardize your promotability or derail your meteoric rise.

1.Take stock. In your 20’s, it’s unlikely you really know what makes you professionally happy. You’re still acquiring knowledge of yourself and trying new things. Says Dillon, “What might make you happy in a job is not always what you think. You may start out making professional choices where the rewards are extrinsic – impressing people with travels, salary, promotions, or working for a premier brand. But those may not be what truly sustains your motivation and keeps you engaged. Bullets on a resume that don’t excite you will sap your energy and passion, not grow it.” Pay attention to what makes you feel most alive. What are the stories you want to tell your closest friends that you don’t need to impress? When do you feel like you’ve made your best contribution? These are the indicators that should point you toward longer-term career choices, not choices you believe will make you look successful or impressive.

2.Monitor discretionary choices. Being mindful of how we use our time is much more than just “work-life” balance. Many millennials pride themselves on how they allocate their time between work and social activity. But just because you allocate your time over a variety of activities doesn’t mean you’re happy. Says Dillon, “You may have binge-watched six episodes on Netflix on a Saturday afternoon, be even less fulfilled when you’re finished, and not even know it. You could have used that time to catch up with a friend or call your mom.” We all make discretionary choices that reveal what is truly important to us . Ask yourself, what’s the most important thing in my life? Then, urges Dillon, “Go to your calendar. Analyze every discretionary hour you’ve spent on that most important thing. Analyze where your resources –your time, talent, passion – are going. If that most important thing isn’t getting the most of your discretionary resources, it’s not really the most important thing to you. And it’s time to be honest about that. If what you claim is important and where you’re putting your discretionary resources don’t match, you’re already off track.”

3.Read all the signs. We all look for signals that our accomplishments are accumulating toward greater success. But sometimes the signals we are reading may not tell the full story. Greater career success isn’t necessarily an indicator of greater joy . Dillon says, “Achievement is very addictive. We want to excel. We want to be labeled ‘high potential’, and we want to emulate the bosses who have the power to give us that label. They hold out shiny trophies indicating success. A sexy project, a promotion, favored-status among peers. Such things make it very hard to remain true to yourself.” Many of today’s professionals grew up with parents who believed that the right nursery school played a role in getting into the right college. We’ve programmed people to think that every step parlays into the next step. It’s seductive to view every project, every assignment, every meeting in which you are called upon to present, as an important sign you are on the path to success. But reading those signs while ignoring others can be dangerous. If you suddenly fell gravely ill, are you confident you know who would be there to help? Are you getting as many cards and messages on your birthday as you used to? Were you blindsided when you weren’t asked to be in that wedding? Dillon reflects, “Don’t get so wrapped up in yourself that you start attaching meaning to everything. You’ll just be disappointed when you realize what you thought was a career-changing moment was completely inconsequential. A very close friend of mine who I’d been meaning to reconnect with suddenly got sick and died. There are some things in life for which you don’t get do-overs. There are some things where you just can’t say, ‘I’ll get to that tomorrow.’”

4.Feel the pang. If we listen closely, we have internal barometers pulling at our hearts telling us something is amiss. Sadly, many learn to suppress or numb the ache. But it starts when you realize important life moments have come and gone without you. Dillon cautions, “It’s starts slowly. At first, you miss a wedding, a baby shower or a grandparent’s 50th anniversary party. You rationalize that at least you sent a gift. Then you are cancelling weekend plans with friends. If you don’t feel those pangs, they get stronger. Suddenly you’re not being included in important life moments of people you love. You get dropped off invite lists to sacred events or, worse, you start getting forgotten by people you swore you’d never lose touch with. That’s when you know your career has taken a disproportionate position in your life. Now, you are compromising.” When I reflect back with my clients over long, accomplished careers, the regretful tears in their eyes are always over things they missed out on, the relationships they wished they’d kept a priority. The client noted above wisely confessed, “If I said to you ‘If I’d only known then…’ I’d only be kidding myself. Because the truth is, I did know then. I just didn’t have the courage to make different choices.”

5.Make choices with purpose. It may be difficult to define a crystal clear life purpose at 25 because you simply haven’t lived enough life. But you can begin to. Ask yourself where you are making the greatest difference. When are the intrinsic rewards as great, or greater, than the extrinsic rewards? Dillon says, “Your life’s purpose may shift over time. It’s not a question you answer overnight. But you know it because it’s the cause you sacrifice for, the thing that makes your heart beat. It both exhausts and energizes you. You’d feel great about doing it even if no one knew you were doing it. It makes you feel part of something greater than yourself.” Dillon suggests that a life purpose should guide you in making both big and small choices. It should set boundaries around values and priorities and lead you closer to the most fulfilling life you could imagine. She notes, “In our research, it was interesting to discover that 97% of successful companies ultimately found their success with a very different strategy than the one they thought they were building. No company, no person, comes out ready to live the perfect formula they initially conceived.”

There is no perfect formula for a great career or life. But there are clear-cut ways to screw them up. Imagine it were decades from now, and your best friend was giving your eulogy at your funeral where you’d lived into your 80’s. What do you hope they would say? Don’t wait to find out. Start building the career, and living the life, that ensures you are the person you’d want your best friend proudly reminiscing to the world about after you’re gone.
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