Take Advantage of that Transition Time in Your Life

I was worn out. I’d been flying around the country for years, chasing big deals with my team, with intense pressure to close them. Our company needed the cash. I was caught between two top executives secretly undermining each other. And I was beginning to recognize that the fit between the company and my values was steadily evaporating.

I wasn’t taking care of myself. Slowly losing touch with my family and friends. Feeling frequent stress and pressure.

The excitement I had felt when we were starting up was slowly dissipating, like air leaking from a small hole in a balloon. I kept going for long runs around the lake, wondering if it was time to move on.

Then one day, I did. I’d had enough. I finally realized it was time.

So I jumped off the train.

I took my life back.

I felt alive and free. And I didn’t leap right away to the next thing. I knew I needed time to detox.

I gave myself an expansive self-imposed sabbatical. A healthy chunk of time to recover and renew. To get my health back. Time to regroup—and to find my way back to myself. I was fortunate to be able to do that. It’s one of the best decisions I ever made.

I was in transition. And that transition needed time and space to play out without me forcing it.

We all go through transitions in life and work. Some are planned, while others are imposed upon us. Some feel great. Others can be excruciating.

Transitions are common: Youth to adulthood. School to work. From living alone to being in a relationship, or in a marriage, or with a family. Back to school. New job or career. A new city, state, or country. New friends and interests. Transition to midlife, and to retirement, and to elderhood. Breakup or divorce. Empty nest. Illness. Loss of a loved one or pet. Becoming a caregiver.

One thing is certain: transitions are on the horizon. They’re coming for us. Transitions are inevitable.

“Everything changes and nothing stands still.” -Heraclitus, 360 BCE

Given their inevitability, we must learn to live with and manage them. Otherwise they can consume us or take us to dark places.

In his excellent book, Life Is in the Transitions: Mastering Change at Any Age, author Bruce Feiler distinguishes between what he calls “disruptors” (regular challenges and setbacks) and “lifequakes” (which can rock our world). He defines a lifequake as a “forceful burst of change in one’s life that leads to a period of upheaval, transition, and renewal.”

How does this play out over the course of a lifetime? Combining the two, Feiler explains:

“The number of disruptors a person can expect to experience in an adult life is around three dozen. That’s an average of one every twelve to eighteen months…. But every now and then, one—or more commonly a pileup of two, three, or four—of these disruptors rises to the level of truly disorienting and destabilizing us. I call these events lifequakes, because the damage they cause can be devastating, they’re higher on the Richter scale of consequences, and their aftershocks can last for years.” -Bruce Feiler, Life Is in the Transitions

Feiler adds them up, and the totals are jarring: “The average person goes through three to five of these massive reorientations in their adult lives; their average duration, my data show, is five years. When you do the math, that means nearly half our lives are spent responding to one of these episodes” (disruptors or lifequakes).

Looking back on my own life, I see tons of transitions. Moving around so much during my childhood. Then moving to London for grad school, later moving to Sweden with my family, and then back to the U.S. after ten years. Transitioning from a nonprofit think tank to an education foundation to an online education startup company. Starting my own company, and then a partnership. Getting married. Becoming a father. Transitioning to midlife.


Typology of Transitions

Our transitions can be personal or collective. Personal transitions are individual changes related to our health, finances, work, etc. Collective transitions are ones we go through together, such as the coronavirus pandemic, global financial crisis, or 9/11.

Our transitions can also be voluntary, such as deciding to get a degree or change jobs, or involuntary, such as getting fired or becoming ill. Feiler notes that most lifequakes are personal and involuntary. Ouch.

And he shows how smaller disruptors can become bigger lifequakes. For example, some disruptors occur at a moment of personal vulnerability, such as when we’re already burned out or having relationship problems. Or it can be the last straw: when one disruptor occurs at the end of a long string of them, causing us to snap. Or it can be a “pileup”: when many disruptors clump together suddenly, much like a traffic pileup on a busy freeway.


The Difficulties

Transitions are hard. They trigger all sorts of stresses and fears, changing our mental state and our physiology.

And they’re messy. When we’re in transition, we’re leaving something known behind for something new and uncertain. We’re grasping in the dark, suspecting danger right around the corner.

We can lose not only our sense of stability and security but also our identity. We begin to doubt ourselves.

When I left that intense job after months of deliberation, I didn’t know what I would do next. I thought about waiting—playing it safe and lining new things up before I left. That can be a smart play. But it didn’t feel right to me then.

I wanted to give it my all when I was in it and then leave it when I felt I couldn’t anymore—or didn’t want to. I sensed I needed down time to get whole again before figuring out my next move.

It’s unsettling to be in that in-between mode, without clarity our resolution. Who are we without that title and the social capital that we believe comes from our position? Can we handle the gaps, with all their perceived judgment and perhaps even rejection or condemnation?

“People who can tolerate the painful discrepancies of the between-identities period, which reflect underlying ambivalence about letting go of the old or embracing the new, end up in a better position to make informed choices. With the benefit of time between selves, we are more likely to make the deep change necessary to discover satisfying lives and work and to eventually restore a sense of community to our lives.”Herminia Ibarra, professor, author, and career change expert


The Benefits

Though surely difficult, transitions also come with a host of benefits, many of them unacknowledged. Here’s a short list of eight main benefits:

  1. Transitions can lead to a better situation, or even a breakthrough.
  2. They’re opportunities for a “do-over,” when we can think and act anew, taking advantage of the tabula rasa.
  3. Transition time is alive time—when things are new or challenging, and when our lives are on the line. The adrenaline surges. Our hearts beat faster as we relinquish safety and venture forth into the unknown.
  4. Transitions allow us to slough off the masks we wear for others and to become ourselves more fully again. We can stop pretending and have the courage to be who we really are, even as we fear the reactions or rejection of others.
  5. When managed well, transitions can lead to powerful and memorable moments in life. Psychiatrist and author M. Scott Peck writes, “Our finest moments are most likely to occur when we are feeling deeply uncomfortable, unhappy, or unfulfilled. For it is only in such moments, propelled by our discomfort, that we are likely to step out of our ruts and start searching for different ways or truer answers.”
  6. Transitions are a real opportunity for a fresh start, when we set down old obligations and get a taste of true freedom once again.
  7. They’re an opportunity to reassess and determine if there’s a gap between the life we have and the one we want. Those gaps can last years, or even decades, as we drift through life, so even painful transitions bear a gift with the wakeup call that can lead to needed change.
  8. Getting good at managing change and transitions is a key leadership capacity. According to leadership expert Warren Bennis in his classic book, On Becoming a Leader, “the one competence that I now realize is absolutely essential for leaders—the key competence—is adaptive capacity. Adaptive capacity is what allows leaders to respond quickly and intelligently to relentless change.”


The Mistakes We Make in Transition

Despite their relative frequency, transitions generally don’t occur often enough for us to develop natural capacity to manage them. We have to work at it. Meanwhile, we tend to make mistakes, adding to the pain. Here are some common mistakes:

-Awaiting perfect clarity before making a decision or taking action. So we never get off the starting blocks, or we wait much too long.

-Having unrealistic expectations about the pace or scope of change.

-Rushing it, often because we’re feeling behind. Premature decisions can set us up for failure by trapping us in recurring negative patterns.

Going it alone, trying to solve complex life equations without tapping into the wisdom of others who’ve been there before and the support of people who can witness our suffering and sit with us so we don’t feel so scared and alone.

-Choosing for the wrong reasons, such as the desire to please our parents or impress our friends and colleagues. A sign of the prestige magnet” in action.

-Being confined by our past, our relationships, or our self-identity (e.g., “I’ve been a lawyer since I was in my twenties, many of my friends are lawyers, and I don’t know who or what I’d be if I weren’t practicing law”).

“We are products of our past, but we don’t have to be prisoners of it.” -Pastor Rick Warren, The Purpose Driven Life

-Wallowing in negative thinking, focusing on the worst case, or ruminating on mistakes or sleights. These only place us in a mental prison of our own making.


Tips for Navigating Transitions

Since many transitions are so hard, we’re bound to fumble through them at certain points. Still, there are things we can do to lighten our load. Here are some quick tips:

-Take care of yourself. Invest in good sleep, exercise, nutrition, socializing, hobbies, and other self-care practices. Without these, everything else will just be harder.

-Develop healthy routines and rituals, leveraging the power of habit. Find what works for you, potentially including exercise, breaks, meditation, prayer, reading, journaling, sleep, and more—especially in the morning and before bed.

-Look for small wins and take a systematic, intentional approach, avoiding the temptation to try to force a breakthrough. Take it one step at a time. Slow and steady wins the race, as long as we’re also awake to opportunities and willing to take action.

“When you improve a little each day, eventually big things occur…. Don’t look for the quick, big improvement. Seek the small improvement one day at a time. That’s the only way it happens—and when it happens, it lasts.” -John Wooden, legendary basketball coach

-Avoid premature resolution. Try to hold out longer in the fog of transition time. Be sure to give yourself adequate time and space to do the necessary inner work of reflection, conversation, pattern-spotting, meaning-making, and experimentation.

“This is now my #1 tip for changing your life. You need to clear a space for the new you to emerge.”Joanna Penn, author

-Get clear about your individual purpose, values, vision, strengths, and passions. These can serve as a safe harbor to return to when you hit storms in your life. They give your life meaning as you tease out the patterns from your personal history.

“Faced with crisis, the man of character falls back upon himself.” -Charles de Gaulle

-Be willing to join the dance of change, alternating between leading the dance, being led by others, and observing yourself in the dance from afar with your mental observer (your ability to step out of your unintentional thought flow and observe your thoughts and reflect on your life).

“The only way to make sense out of change is to plunge into it, move with it, and join the dance.”Alan Watts, philosopher

-Expect and embrace imperfection, messiness, and the unexpected. “Don’t let the perfect be the enemy of the good,” as the saying goes.

-Focus on changing yourself, not others, and focus on what’s in your control, not on complaining about the way things are.

-Recognize your abilities and assets—and all the previous transitions you’ve navigated. Have a little faith.

-Give yourself grace and practice self-compassion. Recall that transitions are hard for everybody.

-Let go of relationships that are no longer serving you. As terrifying as this can be, sometimes it’s the missing key that will unlock a better future, though it’s likely to take time, pain, grief, and healing.

-Reframe change and transition from something to be avoided to something that’s natural, inevitable, and an exciting opportunity for an adventure and growth. View it as a challenge to overcome, or a puzzle to solve. Transitions can be great opportunities for learning and growth.

“If there is no struggle, there is no progress.” -Frederick Douglass

-Lean on your support network and don’t go it alone. Talk to family and friends. Lean on a mentor, coach, or therapist. Join a small group, perhaps a men’s group or a women’s group.

-Think creatively and boldly about potential change, even fundamental change, over time (while also not rushing it and remembering the power of small wins in the meantime). Otherwise, we risk settling for poor or mediocre outcomes and wasting the potential embedded in the transition.

“In a chronically leaking boat, energy devoted to changing vessels is more productive than energy devoted to patching leaks.” -Warren Buffett, investor

“Do not be too timid and squeamish about your actions. All life is an experiment.” -Ralph Waldo Emerson


Closing thoughts: As much as we can struggle with them, we should give ourselves more transition times in our lives. Too often, we stick it out in a sub-optimal situation for too long.

We should also work to get good at them, allowing ourselves to transform as we learn and grow and as the world changes around us. As we do so, we reduce our self-inflicted wounds and have more time and space to enjoy our lives.

Give yourself more transition time—and get good at it.


Reflection Questions

  • Are you in need of a voluntary transition? Have you been waiting too long? What’s holding you back?
  • Are you taking advantage of the transition times in your life, or jumping right away to the next thing?
  • How can you get better at navigating the disruptors and lifequakes you experience?


Postscript: Quotations on Transitions and Change

  • “To be in transit is to be in the process of leaving one thing, without having fully left it, and at the same time entering something else, without being fully a part of it.” -Herminia Ibarra
  • “It is when we are in transition that we are most completely alive.” -William Bridges
  • “She knew this transition was not about becoming someone better but about finally allowing herself to become who she’d always been.” -Amy Rubin
  • “To change one’s life: Start immediately. Do it flamboyantly. No exceptions.” -William James
  • “All great changes are preceded by chaos.” -Deepak Chopra
  • “Getting over a painful experience is much like crossing monkey bars. You have to let go at some point in order to move forward.” -C.S. Lewis
  • “Sometimes good things fall apart so better things can fall together.” -Marilyn Monroe
  • “The measure of intelligence is the ability to change.” -Albert Einstein
  • “Yesterday I was clever, so I wanted to change the world. Today I am wise, so I am changing myself.” -Rumi
  • “When we are no longer able to change a situation, we are challenged to change ourselves.” -Viktor E. Frankl, Man’s Search for Meaning
  • “Learning to make meaning from our life stories may be the most indispensable but least understood skill of our time.” -Bruce Feiler, Life Is in the Transitions
  • “Not in his goals but in his transitions is man great.” -Ralph Waldo Emerson



Gregg Vanourek is a writer, teacher, facilitator, and speaker on personal development, life design, and leadership. He is co-author of three books, including LIFE Entrepreneurs: Ordinary People Creating Extraordinary Lives (a manifesto for integrating our life and work with purpose and passion, co-written with Christopher Gergen) and Triple Crown Leadership: Building Excellent, Ethical, and Enduring Organizations (called “the best book on leadership since Good to Great,” co-written with Bob Vanourek). Sign up for Gregg’s newsletter, access his Manifesto on the Common Traps of Living, or check out his TEDx talk.


Topics: transitions, life transitions, work transitions, career transitions, life design, personal growth, personal development, self improvement, self-leadership, designing your life, crafting your life

The Powerful Pull of the Prestige Magnet

One of the things I enjoy most about teaching is not only engaging with students about the subject at hand but also how it may contain deeper lessons that apply to their life and work. The class readings are a reliable vehicle to those insights.

One of my favorite insights recently comes from Paul Graham, the programmer, entrepreneur, writer, and investor behind the acclaimed tech startup accelerator, Y Combinator. In his article, “How to Do What You Love,” he writes about the dangers of prestige:

“You shouldn’t worry about prestige. Prestige is the opinion of the rest of the world. This is easy advice to give. It’s hard to follow, especially when you’re young. Prestige is like a powerful magnet that warps even your beliefs about what you enjoy. It causes you to work not on what you like, but what you’d like to like.” -Paul Graham

This notion of a prestige magnet has stuck with me (and many of my students), in part because I think it’s so universal and insidious.

The peril of the prestige magnet is that it can pull us into a strange and unhappy vortex in which we’re avidly pursuing prestige while making ourselves—and often those around us—miserable in the process. A dangerous downward spiral.


Signs of the Prestige Magnet in Action

You may think that you’re not susceptible to the pull of the prestige magnet. You may be thinking, I’m not self-centered. I’m not overly ambitious or too concerned about status and prestige.

Most likely, though, you’d be wrong. Our brains are brilliant at helping us deceive ourselves.

“There are two kinds of egotists: Those who admit it, and the rest of us.” -Laurence J. Peter

Here are some telltale signs of the prestige magnet in action:

  • Wanting a pair of cool sneakers or jeans to impress your friends when you’re a teenager.
  • Enjoying the signaling of social status through the car you drive, the part of town you live in, or where you go on vacation—and the attendant social media posts broadcasting it.
  • Secretly hoping that or enjoying it when your degree, profession, title, or organization conveys status to you.

Let’s be honest. We all want prestige—or have wanted it at some point. It’s baked into human nature.

In a recent “How to Build a Life” column for The Atlantic, Arthur Brooks notes recent studies indicating that the biggest goal in life for American children aged 10 to 12 is fame, and a survey of British children found that “YouTuber” was the most coveted career choice.

Evolutionary psychologists note that we can acquire social status either through dominance or prestige (or both). It’s important because high-status individuals tend to receive more protections from their social group, appear more attractive (giving them reproductive advantages), obtain more resources, and have better health and longevity.

Meanwhile, many of us go through an education system that points to prestige pursuit as the standard recommended option (so ingrained that it’s often simply assumed and not even explicit), and we live in a culture that prizes, and sometimes idolizes, status and wealth.


How the Prestige Magnet Can Warp Our Lives

Clearly, there are advantages of social status, and we shouldn’t hold it against people for deriving benefits from their hard work, commitment, courage, or creativity. Far from it.

But there are also disadvantages, some of which are not only costly but also underappreciated.

Here are nine of the main disadvantages:

1. Career Choices

The prestige magnet can keep us from doing what we really want to do, or what we’re better suited to do, or from pursuing our dreams. It can pull us into career fields for the wrong reasons that don’t hold up over time, and with high switching costs (or even a sort of lock-in effect). I recall how popular and prestige-soaked the fields of consulting and investment banking were when I was getting my MBA. The point isn’t that there’s anything wrong with those professions but rather whether those jobs were a good fit for all those classmates and whether there wasn’t a phenomenon of social contagion at work. (And yes, I dipped my toes in those waters too. Let me be clear: I struggle with this trap, among many others, as well.)

2. Addiction

We can become addicted to the pursuit of prestige and its close cousins (success, fame, wealth, etc.), with all the implications that addictions carry, including crowding out other important areas of our lives, like health, relationships, and peace of mind.

3. Happiness Effects

By pursuing prestige, aren’t we placing parts of our happiness and sense of self-worth into the hands of others, including people we don’t even know or like?

4. The Expense

Pursuing prestige can be expensive, from costly universities to the pricey cars, homes, neighborhoods, and lifestyles that put us on a financial hamster wheel, sprinting to try to keep up. Getting nowhere fast. It can be exhausting—and financially precarious if things go awry.

5. Hidden Costs

Prestige often comes with hidden costs, including:

    • feeling trapped in jobs we don’t like, sometimes with colleagues or bosses we don’t like
    • working excessive hours (many prestigious firms pride themselves on this, as a sort of twisted bragging right)
    • burying ourselves in spreadsheets or presentation decks
    • wondering if our sacrifices are worth it
    • experiencing stress, anxiety, or depression

6. Career Damage

Those who are chasing status and prestige can come across as self-centered and self-serving, which can impair their teamwork and leadership effectiveness, because it’s off-putting. It can even take people on a path to becoming a toxic leader.

7. Identity Effects

If we’re consumed by a hunger for status and prestige during our career, where is that likely to leave us when we retire or if we change jobs or need to stop working? Are we okay with who we are even without the recognition or status? Do we need to be viewed as successful to feel content or happy?

8. Relationship Pain

Being in hot pursuit of prestige can keep us away way too much from those we love, from our spouse or significant other to our children, parents, or close friends. How will we view those tradeoffs and compromises later in life?

9. Regret

Following the prestige path is likely to lead to painful regret down the road, with a rude reckoning for our choices.

We can note here that many of these disadvantages, in the larger scheme of things, are problems of privilege. Many people struggle with much nastier problems, like surviving and feeding their families. Still these problems of the prestige magnet come with real pain and damage for many, and they’re found on all levels of the socioeconomic spectrum.

So now we must ask, what to do about it?


How to Demagnetize the Prestige Magnet

From science class, we may recall that physical magnets can be demagnetized via certain techniques. For example, via high heat. Or a reverse field. We can even hammer the magnetism out of it. Best of all, we can leave the magnet untouched for long periods of time, and demagnetization will occur naturally over time. Like magic.

The prestige magnet can also be altered. Here are ten ways to address it:

1. Why

Step back and consider why you’re pursuing prestige, including whether there’s some sort of pain, loss, or hurt in your life that you’re trying to numb—and whether you might address it better by going to its roots.

2. Who

Think more critically about who you’re trying to impress. Who are they? How much do they truly matter to you? How likely is it that they’ll matter to you long in the future? Are they really so concerned about you, or are they more likely to be caught up in their own concerns, including their own prestige magnet?

3. Work

Instead of dwelling on how you stack up, focus on the work itself. Get lost in the process and concentrate on creating value for the intended beneficiaries. Become a craftsman and focus on slow, steady, and systematic improvement.

4. People

Spend your time with people who are comfortable with who they are regardless of the vagaries of status—and who care more about your heart and soul than your status and prestige.

5. Service

Serve others. Leave the prestige pursuit behind and focus on helping others. Be part of a community and contribute to something larger than your own personal wants, needs, and insecurities. If you’re in a position of authority, consider practicing servant leadership, a counterintuitive and revolutionary approach to leadership that emphasizes serving others first, including developing them and helping them accomplish things they never thought possible.

6. Purpose

Discover and pursue your purpose, or something that feels significant or meaningful to you, or that captures your heart. This will get your out of your head and into a project or endeavor that motivates you and benefits others. If you’re in a position of authority, consider taking on our triple crown leadership quest—a commitment to building an organization or team that’s excellent (achieving exceptional results and positive impacts for all stakeholders), ethical (doing the right thing, even when it’s costly or hard), and enduring (standing the test of time and operating sustainably).

7. Gratitude

Be grateful for what you have. Incorporate gratitude practices (e.g., prayers of thanksgiving, meditation, a gratitude jar) into your life. And determine what is enough for you so you don’t catch the “disease of more.”

8. Creation

Build or create something: a side hustle, blog, passion project, memoir, garden, novel, startup, or social venture—whatever captures your interest and gets you lost in a state of flow.

9. Mortality

Think about your death. That’s right. As morbid as it is, remembering that you’re mortal—and given an unknown time span on this Earth—can help you remember what’s truly important in life—and what’s not.

10. Resolve

Decide and declare that you don’t need validation from others to determine your worth. Change your focus from worrying about what others may think of you to putting your head down and being the best person you can be, growing and giving as best you can every day.

The prestige magnet has its pull on many of us these days. Thankfully, though, there are many things we can do to dull its effect while still thriving in our chosen endeavors.


Reflection Questions

  1. How strong is the prestige magnet in your life?
  2. What can you do to reduce its downsides without eliminating its upsides?



Related Traps

This prestige trap doesn’t exist in a vacuum. It’s related to many of the other traps we’ve been addressing this traps series, including:



Postscript: Inspirations on Prestige and Ego

  • “Ego is the enemy.” –Ryan Holiday
  • “The bigger your heart, the more you love, the more you control your life. The bigger your ego, the more you’re scared, the more others control your life.” –Maxime Lagacé
  • “Egotism sucks us down like the law of gravity.” -Cyril Connolly
  • “Don’t worry about looking good; worry about achieving your goal.” –Ray Dalio
  • “The only way to escape the corruptible effect of praise is to go on working.” -Albert Einstein
  • “We must do our work for its own sake, not for fortune or attention or applause.” –Steven Pressfield (from The War of Art)
  • “Avoid having your ego so close to your position that when your position falls, your ego goes with it.” -Colin Powell
  • “Prestige is especially dangerous to the ambitious.” -Paul Graham
  • “When the ego dies, the soul awakes.” -Mahatma Gandhi
  • “The foundation of the Buddha’s teachings lies in compassion, and the reason for practicing the teachings is to wipe out the persistence of ego, the number-one enemy of compassion.” –Tenzin Gyatso, 14th Dalai Lama
  • “The ego is a veil between humans and God. In prayer all are equal.” -Rumi



Gregg Vanourek is a writer, teacher, facilitator, and speaker on personal development, life design, and leadership. He is co-author of three books, including LIFE Entrepreneurs: Ordinary People Creating Extraordinary Lives (a manifesto for integrating our life and work with purpose and passion, co-written with Christopher Gergen) and Triple Crown Leadership: Building Excellent, Ethical, and Enduring Organizations (called “the best book on leadership since Good to Great,” co-written with Bob Vanourek). Sign up for Gregg’s newsletter, access his Manifesto on the Common Traps of Living, or check out his TEDx talk.


Topics: prestige, prestige magnet, ego, status, life design, personal growth, personal development, self improvement, self-leadership, designing your life, crafting your life

Why We Want Adventure in Our Lives—And How to Get It

Afoot and light-hearted I take to the open road, Healthy, free, the world before me. -Walt Whitman

Adventure. It’s an amazing part of life and work, but often overlooked and neglected.

When I was little, my Dad used to tell stories to my brother and me—always about an adventurer, with a rucksack, off on some expedition. We loved it, in part because of the surprise and danger.

It turns out that adventure has much to teach us about living and leading. Of course, it’s not often that we encounter opportunities for exciting, daring, hazardous undertakings of unknown outcome.

But what if we could cultivate adventure in our lives?
What if we could pursue grand and meaningful adventures in our work?


The Benefits of Adventure

Adventure isn’t something just for daredevils and skydivers. It’s something for all of us who want to live well.

Adventure makes us feel more fully awake, alive, and free. It feeds us with the energy and excitement of exploration, discovery, and surprise. It even comes with a physiological response, with norepinephrine (a neurotransmitter that increases alertness and arousal) and elevated respiratory and heart rates.

“The danger of adventure is worth a thousand days of ease and comfort.”Paulo Coelho, Brazilian novelist

Adventure comes with many benefits:

  • Adventure can give us remarkable experiences to savor and extraordinary memories to cherish.
  • It helps us discover who we really are (or rediscover it), which can be hard to do if we’re constantly mired in responsibilities, expectations, pressures, deadlines, and incessant busyness.
“…your dreams come clean over miles of road.” -Jackopierce, from their song, “My Time”
  • Adventure can help us feel whole again, especially if we’ve been living a divided life, and reconnect with our heart and intuition.
  • It can help us learn and grow, as we face new situations and challenges and try to improvise our way through them.
“Change and growth take place when a person has risked himself and dares to become involved with his own life.” -Herbert Otto
  • Adventure can help us develop our strength and courage as we learn to confront our fears.
  • It gives us an opportunity to transcend limiting beliefs. (In turn, we can move forward toward fulfilling our potential, learn how to trust ourselves, and develop a greater sense of our own agency.)
  • Adventure can lead to the accomplishment of great things, none of which would have been possible if we hadn’t dared to try.
“Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much because they live in the gray twilight that knows neither victory nor defeat.” -Theodore Roosevelt


Ways to Bring Adventure into Our Lives and Work

Despite all these benefits, it’s easy to self-select out of adventure opportunities because of a limited view of ourselves as “not the adventurous type.”

But ceding this territory to the adrenaline junkies and thrill seekers is a mistake, especially since there are so many ways to invite adventure in our lives, some of which are straightforward and accessible for many:

Get out into nature, away from civilization and noise, and venture out into new areas. (You can also take it up a notch and do something like an Outward Bound expedition.)

“In the middle of the forest is an unexpected clearing, that can only be found by those who are lost.” -Tomas Tranströmer, Swedish poet

Travel to new places. (When you do so, be sure to get off the beaten path and take what Clif Bar entrepreneur Gary Erickson calls the “white roads.” When cycling through Europe with a friend, he noticed that, on a map, red roads are the big roads, full of vehicles, noise, and exhaust, while white roads are the smaller, quieter, less traveled paths full of surprises.

“Travel changes you. As you move through this life and this world you change things slightly, you leave marks behind, however small. And in return, life—and travel—leaves marks on you. Most of the time, those marks—on your body or on your heart—are beautiful.” -Anthony Bourdain 

Learn or try something new. Try running, surfing, sailing, rock climbing, scuba diving, snorkeling, kayaking, canoeing, paddle boarding, rafting, triathlons… whatever calls to you.

Sample new cuisine. My friends in Maryland are currently on a quest to eat a meal from every country in the world.

Ask someone out if you’re single. Take that chance even if it scares you. You ever know what might be on the other side of that decision.

Engage more with strangers. You never know what you may learn or encounter—or how much it may mean to someone in need.

Make new friends. Too many people start cocooning later in life after settling down, leading to disconnection, loneliness, and unhealthy over-reliance on a spouse or significant other.

Take advantage of transition times in your life (e.g., after graduating, in between jobs, when the kids leave the home, retirement, etc.). (For a great book on this, check out Life Is in The Transitions by Bruce Feiler.)

Launch or join a startup venture, or an innovation initiative or skunkworks project at your workplace. These can be thrilling in their challenges and opportunities—and career highlights.

Break out of a career rut, no longer settling for a bad manager or toxic culture, and finding something more worthy of your efforts and more aligned with your values and aspirations.

Go back to school to help launch you on a different career track that’s a better fit, or just because you’re curious and would like to learn and engage with new people and settings.

If you’re a manager, give your team an epic challenge, or create exciting new experiences for them to break the monotony and invite their creativity.

Join an adventure expedition or festival. There are many options. A summer camp for adults, a Tough Mudder, Burning Man, South by Southwest, and more.

Go on a retreat or a spiritual pilgrimage. Retreats like InsideFirst Roundtables, Modern Elder Academy Sabbatical Sessions, and Inventure expeditions. Pilgrimages to Jerusalem, Mecca, Camino de Santiago (France and Spain), Mount Kailash (Tibet), and Shikoku (Japan) to something more homegrown and local.

Some of my favorite adventures over the years have included:

  • backpacking through Europe
  • studying abroad for a year in London in graduate school
  • camping and climbing a pair of “fourteeners” (mountains rising to 14,000 feet above sea level) in the Colorado Rockies with friends
  • sailing on an overnight felucca boat down the Nile with my brother
  • performing live music at gigs, bars, and coffeehouses
  • trying to learn how to surf in Puerto Escondido, Mexico, spotting a great surfer on the same beach, asking him if he knew anyone around who could give me surfing lessons, and then getting a personal surfing lesson from him and learning that he was an international surfing competitor
  • joining school plays and musicals despite having no background in theater
  • bridge-jumping with a friend at his college
  • canoeing and swimming in a Puerto Rican bay among bioluminescent plankton
  • cliff-diving at an Adirondack lake
  • working at a tech startup that became a scale-up, with all its highs and lows
  • taking a self-generated sabbatical after leaving that startup so I could take my life back
  • getting married
  • becoming a father
  • moving to Sweden, getting out of my bubble and learning a new culture, language, and worldview (and then moving back to Colorado)

These are some of my fondest memories, but I also see that there have been long chapters in my life in which adventure has been absent.

Thankfully, I’ve been inspired by adventurous friends and colleagues. One friend talked his way onto a naval submarine off the coast of South America so he could hitch a ride down the coastline.

Another favorite of mine: an entrepreneur we interviewed for LIFE Entrepreneurs who retreats to his own “secret office”:

“Each year, I try to take twenty-five work-week days and spend them hiking, biking, or on the water some place. It’s like having your own secret office with the world’s best views. These aren’t bank holidays or the days between Christmas and New Year’s. They’re mid-week days right in the heart of the year when everyone else is at their desk. My best creative thinking is on these days. The places I go are inspiring, and exercise tends to calm my mind and help me see the big picture. Following these days, I try to resist the urge to catch up on emails at night. Instead I’ll write or think about what occupied my mind that day.”Max Israel

If you struggle with jumping on the adventure bandwagon, consider this unconventional motivator:

Contemplate your death.

This ancient practice from the Stoics (memento mori: “Remember that you must die”) and other traditions can help put our lives in perspective while also highlighting their flaws, sparking urgency to grab hold of our lives while we have them.

“Remembering that I’ll be dead soon is the most important tool I’ve ever encountered to help me make the big choices in life. Almost everything—all external expectations, all pride, all fear of embarrassment or failure—these things just fall away in the face of death, leaving only what is truly important.” -Steve Jobs


The most important adventure of all is the one that’s most hidden: everyday life.

Sometimes in the hustle and bustle of daily activity, it’s easy to lose sight of the grand adventure that is life itself. The miracle that we’re here, wandering on a planet hurtling through the cosmos, all part of a wondrous, incomprehensible whole.

How can it all possibly be? What will happen next, in our lives and the world? Why are we here? What will we choose to do with our unknown number of days, and who with, and to what end? A grand adventure, indeed, and the most precious of gifts.


Traps that Keep Us from Having Adventures

There are many pathways into adventure, from the mundane and simple to the morbid and sublime. But let’s not kid ourselves and pretend that it’s always easy, given our circumstances and obligations.

Too often, we fall into the common traps of living, many of which make adventure feel out of reach. Some of the traps:

  • Conforming: conforming to societal conventions or conventional paths.
  • Drifting: getting carried along by time, circumstances, and outside influences.
  • Playing the short game: being short-sighted and neglecting the big picture.
  • Being outer-driven: being driven by external (parent, peer, societal) expectations and caring too much about what other people think.
  • Postponing happiness: deferring plans or dreams because it’s not practical or “the right time.”
  • Settling: compromising or settling for “good enough.”
  • Being a workaholic: being addicted to work or success, letting it consume our thoughts and time while letting other important things slip away.

The traps are tricky. They sneak up on us, sometimes capturing us for years. But they’re not insurmountable.

We just need something worthy of our efforts to break free. Something like the sweet thrill of adventure and the lasting glow it brings.

Do you have enough adventure in your life?
 What can you do, starting today, to invite more adventure into your life and work?


Postscript: Quotations on Adventure

  • “It is remarkable how easily and insensibly we fall into a particular route, and make a beaten-track for ourselves.” -Henry David Thoreau
  • “During the first period of a man’s life the greatest danger is: not to take the risk.” -Soren Kierkegaard
  • “We need the sweet pain of anticipation to tell us we are really alive.” -Albert Camus
  • “Cover the earth before it covers you.” -Dagobert Runes
  • “Security is mostly a superstition. It does not exist in nature, nor do the children of men as a whole experience it. Avoiding danger is no safer in the long run than outright exposure. Life is either a daring adventure or nothing at all.” -Helen Keller
  • “Man cannot discover new oceans unless he has the courage to lose sight of the shore.” -Andre Gide
  • “To dare is to lose one’s footing momentarily. To not dare is to lose oneself.” -Soren Kierkegaard
  • “Only those who dare to fail miserably can achieve greatly.” -Robert Kennedy
  • “Jobs fill your pockets, but adventures fill your soul.” -Jaime Lyn
  • “Adventure may hurt you, but monotony will kill you.” -Marcus Purvis
  • “Life shrinks or expands in proportion to one’s courage.” -Anais Nin
  • “Above all, life entrepreneurship is an adventure.” -Warren Bennis
  • “Broad, wholesome, charitable views of men and things cannot be acquired by vegetating in one little corner of the earth all one’s lifetime.” -Mark Twain
  • “So many people live within unhappy circumstances and yet will not take the initiative to change their situation because they are conditioned to a life of security, conformity, and conservation, all of which may appear to give one peace of mind, but in reality nothing is more damaging to the adventurous spirit within a man than a secure future. The very basic core of a man’s living spirit is his passion for adventure.” -Jon Krakauer, Into the Wild


Bonus: Inspiring Adventure Classics

Many of us cherish the classic adventure stories from literature and film that inspire our dreams and ambitions. Some of my favorites:

The Lord of the Rings

J. R. R. Tolkien took us on an epic ring quest. Starting in the Shire, the hobbits Frodo, Sam, Merry, and Pippin band together with other wily characters like Gandalf, Aragorn, Legolas, Gimli, Arwen, Galadriel, Boromir, and others to take on Sauron, Saruman, the Orcs, Trolls, and more hideous creatures and wizards and try to destroy the Ring in Mount Doom, thereby saving the world. It’s a classic tale of courage and good versus evil, wrapped in a brilliant adventure.

“It’s a dangerous business, Frodo, going out your door. You step onto the road, and if you don’t keep your feet, there’s no knowing where you might be swept off to.” -Bilbo Baggins, a character in J. R.R. Tolkien, The Lord of the Rings: The Fellowship of the Ring

The Odyssey

In this epic poem by Homer, Odysseus struggles to endure the wrath of the gods, smite mystical creatures, and survive daunting threats—from a cyclops and witch to a sea storm and the alluring Sirens—in a decade-long struggle to return home to his wife, Penelope.

“A man who has been through bitter experiences and travelled far enjoys even his sufferings after a time.” -Homer, The Odyssey

Into the Wild

This book by Jon Krakauer recounts the spirited adventures of Christopher McCandless (a.k.a., “Alexander Supertramp”), a young man disillusioned by the conventions of civilized life in suburban Virginia and its soul-sapping monotony. He gave up his possessions, donated his college fund to charity, and embarked on a brand-new path, traveling westward across the country, abandoning his car after a flash flood, and then hitchhiking to the Stampede Trail in Alaska, where he set off alone in the snow with only ten pounds of rice, a camera, a rifle, ammunition, and some reading.

“I now walk into the wild.”Jon Krakauer, Into the Wild

Harry Potter

J. K. Rowling’s fantasy novels tell the story of Harry Potter, a young wizard touched by fate, and his friends and allies Hermione Granger, Ron Weasley, Albus Dumbledore, and Hagrid. Their escapades at the Hogwarts School of Witchcraft and Wizardry place Harry in harrowing battles against Lord Voldemort, the dark wizard.

“Let us step into the night and pursue that flighty temptress, adventure.”J. K. Rowling 


Sir Ernest Henry Shackleton was an explorer who led three expeditions to the Antarctic in the 1900s. During the Nimrod expedition, he and his crew made the largest advance toward the South Pole in history. After subsequently losing the race to the South Pole to Roald Amundsen, Shackleton focused on crossing Antarctica from sea to sea via the South Pole. During this expedition, its ship, Endurance, became trapped in ice and was gradually crushed. The crew camped on the sea ice and then launched lifeboats and traveled an incredible distance to reach Elephant Island and then South Georgia Island.

“Men wanted for hazardous journey. Small wages. Bitter cold. Long months of complete darkness. Constant danger. Safe return doubtful. Honor and recognition in case of success.” -newspaper ad placed by Sir Ernest Shackleton to recruit a crew for his Antarctic expedition


Bonus: Gregg’s Curated Music Playlist for Your Next Adventure

  • “8 Miles from a Paved Road,” Edwin McCain
  • “America,” Simon and Garfunkel
  • “Beautiful Day,” U2
  • “Can’t You See,” The Marshall Tucker Band
  • “Drift Away,” Dobie Gray
  • “Fast Car,” Tracy Chapman
  • “Free,” Jackopierce
  • ‘Hit the Road Jack’ by Ray Charles
  • “Into the Mystic,” Van Morrison
  • “I Want to Get Lost with You,” Stereophonics
  • “My Time,” Jackopierce
  • “On the Road Again,” Willie Nelson
  • “Peaceful, Easy Feeling,” The Eagles
  • “Ramblin’ Man,” Allman Brothers Band
  • “Roam,” The B-52’s
  • “Route 66,” Chuck Berry
  • “Runnin’ Down a Dream,” by Tom Petty
  • “Running on Empty,” Jackson Browne
  • “Seven Bridges Road,” The Eagles
  • “Shotgun Rider,” Tim McGraw
  • “Southern Cross,” Crosby, Stills, and Nash
  • “Take It Easy,” The Eagles (or the original Jackson Browne version)
  • “The Mountains Win Again,” Blues Traveler
  • “Vineyard,” Jackopierce
  • “Where the Streets Have No Name,” U2

What are your favorite adventure or road-tripping songs? Contact me here to send me suggestions for this list.


Gregg Vanourek is a writer, teacher, facilitator, and speaker on personal development, life design, and leadership. He is co-author of three books, including LIFE Entrepreneurs: Ordinary People Creating Extraordinary Lives (a manifesto for integrating our life and work with purpose and passion, co-written with Christopher Gergen) and Triple Crown Leadership: Building Excellent, Ethical, and Enduring Organizations (called “the best book on leadership since Good to Great,” co-written with Bob Vanourek). Sign up for Gregg’s newsletter, access his Manifesto on the Common Traps of Living, or check out his TEDx talk.

Topics: adventure, daring, courage, life design, personal growth, personal development, self improvement, self-leadership, designing your life, crafting your life