Resetting Your Career in Midlife

"Midway upon the journey of our life,” writes Dante in the first lines of his Inferno, “I had found myself in the dark wilderness, for I had wandered from the straight and true.”

I wonder if Dante was making a comment on the crafty nature of sin, creeping up from behind like a silent fog when we least expect it…or just the bewildering challenges of being middle-aged.

Several weeks ago, I called Dan, one of my friends, who’s nearly forty. “How are you?” I asked. “Well, nothing new,” he said with sigh. “Same job. Same family. Same house.”

He went on to explain that nothing was wrong, per say, other than feeling the reality set in that he was no longer in his twenties, filled with notions of changing the world. He wasn’t depressed, but aspiration had slowly given way to some combination of responsibility and reality, seeing in one hand a mortgage statement and in the other the scars of a thousand tiny disappointments after almost two decades on the job.    

“Midlife, especially for middle-class American men,” wrote Robert Bellah, American sociologist and author of Habits of the Heart, “often marks the end of a dream of a utilitarian self established by ‘becoming one’s own man’ and then ‘settling down’ to progress in a career.” Bellah says that around midlife, many realize that they’ll never be “number one” — senior partner, Nobel laureate, principal, CEO. As these dreams die, finding one’s identity in work dissipates and career trajectories flatten. “For many in middle age, the world of work then dims, and by extension so does the public world at large.”

For years in my own work at DIFW we have seen a trend: young professionals in their twenties and thirties come to our events, press into big social issues, and become Fellows, but participation in our programming drops off in one’s forties and fifties. What’s happening here?

Both my friend Dan and Robert Bellah explain what’s happening. First, in middle age, we must reckon with the crushing loss of professional dreams. You have a job, but the idea that you were going to “change the world” is shown for what it is: a postmodern mirage, built around the slippery, individualistic notion we had believed since we were teenagers: “you can be whatever you want to be.” A cloud of grief, loss, and disillusionment fills our horizon — one we’re quick to push back with entertainment, busyness, or consumerism.

The second reason: golden handcuffs. We reach the midpoint of our careers and we find we’re better paid now than we were in our twenties, but our expenses have grown as well. Mortgage payments, grocery bills, and kid’s activity fees all tamper down our desire to risk building something new, step out on a limb at work, or start a new career. Better to play it safe, even if we feel something inside of us crumbling.

Yet not all submit to the resignation of our hopes in midlife.

I’ve observed that some take an alternative path in midlife that acknowledges our limitations, pursues interior freedom, and embraces failure as the only pathway to growth.

Gordon Smith, author of Courage and Calling,writes, “To embrace our vocations in midlife means that we accept two distinct but inseparable realities. First, we accept with grace our limitations and move as quickly as we can beyond illusion about who we are. Second, it means, positively, that we accept responsibility for our gifts, and acknowledge with grace what we can do.”

Bishop Ken Untener makes a similar point, very applicable to life at midcareer, “We cannot do everything, and there is a sense of liberation in realizing that. This enables us to do something, and to do it very well.”

Our individualistic society is built around “your success.” And most weeks I see people who mistakenly believe that they can find their life’s purpose in their job. When this illusion dies, they often become disengaged — both from their job and the broader culture. And for those who do make it to the top, often they’ve done so by making work their religion.

But some take a humbler path. They take stock of what they are, and what they’re not. They look squarely at their talents and their limitations. They realize they won't change culture. But they also realize that they can change the world right around them — co-workers, community, church, and family.

And perhaps even more importantly, they become ok with knowing people who are richer, smarter, better looking, and more talented. Seeking approval for performance is calmed by the steady, lasting approval of God. 

When New York Times columnist David Brooks set out to explore his own road to character growth, he realized there are two sets of virtues: résumé virtues and eulogy virtues. Résumé virtues are those you bring to the marketplace and post on LinkedIn — degrees, job accomplishments, accolades. Eulogy virtues are virtues people will talk about at your funeral — humility, kindness, courage.

Our careers tend to compensate and reward us for résumé virtues, but at some point, we realize these goals are thin, and we’ll have to decide whether we’ll make the journey into the interior world.

Rev. Jacques Philippe, author of Interior Freedom,says that if we’re continually looking to the external world for our approval, we’ll never be happy because our circumstances are constantly changing. However, he says we can cultivate deep interior freedom by practicing the virtues of faith, hope and love and by connecting deeply to the source of inner freedom — God himself — which no external power can take away.

Philippe and Brooks both are calling us to making a momentous shift in our lives: from exterior success to interior depth.

In this way of thinking, work becomes not just a way to achieve, but the primary context for our spiritual formation and interior growth. When we’re passed over for a promotion, slighted by a prospective client, or enduring a toxic workplace culture, the question becomes not one of escape to a better job, but instead: who am I becoming?

When the journey toward success in midlife loses its luster, a few decide to take a humbler, yet ultimately more exciting journey, one toward whole-heartedness and deep emotional and spiritual health.

Winston Churchill once said, “Success is going from failure to failure without loss of determination.” Commenting on this paradox, Rabbi Jonathan Sacks writes, “It is not their victories that make people leaders; it is the way they cope with their defeats — their ability to learn, to recover, and to grow.”

Most people move into middle age with a growing set of disappoints and failures that lead to resignation. “I’ll never get the job.” “I’ll never make a big impact. That was just the naivety of my twenties.”

Yet there are a few who experience the same set of consistent failures and they learn from them. They adopt a growth mindset. They don’t let their ego get in the way and they instead welcome feedback from family, friends, and co-workers. In the process, they ask questions like: What did I learn from that situation? How did I react? And what does this mean for me and for those around me?

The path to leadership is narrow because the majority want to blame others for their problems. The few decide to take ownership over what they can and let the harsh lessons of life refine them like a fire.

Dante had to make the journey first into the inferno before he made his way to purgatory and then ultimately to paradise.

Perhaps the only way out of the dark wilderness of midlife is first to go further in.