I was sitting on my back deck last Friday, enjoying a good cigar and watching the sunset—one of those rare moments of stillness in an otherwise chaotic week—when a text from an old college buddy popped up on my phone. It was a link to an article about one of our former classmates who had just sold his tech company for an obscene amount of money.

"Remember when this guy could barely code 'Hello World'?" my friend wrote.

I laughed, took another draw from my cigar, and felt that familiar twinge in my gut. You know the one—that nagging sensation that everyone else got the instruction manual for life while you're still trying to assemble your IKEA furniture without all the right parts.

That's the thing about hitting midlife. You've lived long enough to see the scoreboard, and sometimes you can't help but wonder if your tally measures up.

The Midlife Measuring Tape

If you're a Gen Xer like me, you were raised with certain markers of success burned into your brain:

• The corner office by 40
• The house in the right neighborhood
• The impressive title on your business card
• The retirement account that doesn't make you break into a cold sweat
• The family vacation photos that prove you've "made it"

We grew up watching Michael Douglas in "Wall Street" declare that "greed is good" and watching our parents climb corporate ladders with promised gold watches at the end. We entered adulthood during economic booms that made achievement seem inevitable—until life threw curveballs like recessions, pandemics, and the wild realization that everything we knew about work, success, and security was changing right under our feet.

Now here we are, somewhere past 40, looking around and asking, "Is this it? Is this what I was hustling for all those years?"

For many of us, that question comes with a side of uncomfortable feelings:

• The LinkedIn profile you avoid updating because everyone else seems to be announcing promotions
• The high school reunion you skipped because you're not where you thought you'd be
• The conversations with old friends that turn into subtle competitions about kids' achievements or career milestones
• The nagging sense that time is running out to "make your mark"

Sound familiar? I thought so.

When Success Doesn't Feel Successful

Here's a confession: By most conventional measures, I've done okay. I've got the career, the family, the house. I can enjoy a good scotch and a premium cigar on my own deck. I've checked many of the boxes society told me constituted "success."

Yet I've still found myself at 2 a.m., staring at the ceiling, wrestling with the question: "Shouldn't I have accomplished more by now?"

Maybe you've been there too. Maybe you look at that business you never started, that degree you never finished, that book you never wrote, or that promotion that went to someone else, and you feel the weight of untapped potential.

Or maybe you achieved exactly what you set out to achieve, only to discover it wasn't what you really wanted after all.

The problem isn't that we haven't accomplished enough. The problem is how we've defined "enough" in the first place.

The Metric System is Broken

I've been thinking about this a lot lately, especially as I read through the Book of Ecclesiastes. Talk about a midlife crisis! Here's this guy, traditionally thought to be Solomon—the wealthiest, wisest, most successful man of his time—essentially saying, "I've done it all, and guess what? It's meaningless without the right perspective."

He had the ancient equivalent of the corner office, the mansion, and the impressive title. He had more wealth than he could spend in a lifetime. He accomplished more than most people could dream of.

And his conclusion? "Meaningless! Meaningless!... Everything is meaningless!" (Ecclesiastes 1:2)

Not exactly the motivational poster you want hanging in your home office.

But dig deeper, and Solomon's crisis offers profound wisdom for our own. His point wasn't that accomplishment itself is bad. His point was that when we measure our lives solely by worldly standards of achievement, we're using a fundamentally flawed measuring system.

It's like trying to measure water with a yardstick. The tool simply isn't designed for what you're trying to measure.

Beyond the Resume Virtues

The author David Brooks talks about the difference between "resume virtues" and "eulogy virtues." Resume virtues are the skills and accomplishments that you put on your resume. Eulogy virtues are the ones that get talked about at your funeral—whether you were kind, brave, honest, faithful, capable of deep love.

Our culture celebrates resume virtues. We applaud the promotion, the acquisition, the award. We double-tap the Instagram post about the new house or the exotic vacation.

But at the end of a life, what matters more? Which accomplishments bring deeper, more lasting satisfaction?

I'm not suggesting we should all quit our jobs and live in monk-like simplicity (although if that's your calling, more power to you). I'm suggesting that maybe we need to expand our definition of accomplishment beyond the narrow confines of career success and material acquisition.

Redefining Accomplishment

A few years ago, I had a health scare—nothing major in the end, but enough to make me take stock. For a few uncertain weeks, as I waited for test results, I found myself thinking less about my job title and more about relationships, impact, and purpose.

I wasn't mentally reviewing my sales numbers or award plaques. I was thinking about:

• The times I showed up for my kids when it mattered
• The friend whose call I took at midnight when his marriage was falling apart
• The young guys I've mentored at church who are now leading their own families well
• The times I stood by my principles even when it cost me
• The moments I chose kindness over being right
• The marriage that has deepened through challenges rather than broken by them

None of these things would make my resume stronger. None would increase my net worth. But all of them, I realized, were accomplishments of the highest order.

The Currency of Connection

Here's something they don't tell you in those hustle-culture books: Relationships are the most valuable currency we have.

As I've watched friends climb corporate ladders at the expense of their marriages, or chase wealth at the cost of their health, I've realized that many of our traditional metrics of success extract payments in this essential currency.

The scripture puts it plainly: "What good is it for someone to gain the whole world, yet forfeit their soul?" (Mark 8:36)

I'm not saying career success and soulful living are mutually exclusive. I'm saying we need to be intentional about measuring both—and honest about which one we're prioritizing.

When I look back at periods when I felt most "accomplished," they rarely correlate with promotions or purchases. They correlate with times of meaningful connection:

• The weekends spent teaching my son to change his oil and fix things around the house
• The conversations around a fire pit with friends, cigar in hand, talking about things that matter
• The moments of showing up in someone's pain and just being present
• The small group I've led at church where I've seen real transformation in people's lives
• The marriage that has weathered storms and grown stronger

The Impact Beyond the Income

Another metric worth reconsidering: impact versus income.

Our culture has conditioned us to equate financial success with significance. The more you make, the more you matter. I bought into this for years, chasing raises and bonuses as the primary measure of my professional worth.

But what if we measured success by the depth of our impact rather than the size of our income?

I have a friend who left a high-paying corporate job to teach high school. By conventional metrics, this was a step backward—less money, less prestige, a smaller office (if you can call the teachers' lounge an office at all).

But when he talks about helping a struggling kid finally understand algebra, or mentoring students who are the first in their families to apply to college, there's a fulfillment in his eyes I rarely saw during his corporate days.

His world got smaller by conventional measures, but his impact got deeper.

I'm not suggesting money doesn't matter. Bills need paying. Retirement needs funding. Good cigars don't buy themselves. But I am suggesting that when we make income the primary metric of success, we miss out on measuring the things that often bring the deepest satisfaction.

The Timeline Is Longer Than You Think

One of the most liberating realizations of midlife is this: Your story isn't over. Not by a long shot.

Our culture venerates youth and early achievement. We celebrate the 30-under-30 lists and the wunderkinds who make millions before they can legally rent a car. This creates the false impression that if you haven't "made it" by 40, you've somehow missed your window.

History tells a different story:

• Ray Kroc was 52 when he opened his first McDonald's
• Vera Wang didn't design her first dress until she was 40
• Samuel L. Jackson didn't get his breakout role until he was 43
• Julia Child published her first cookbook at 49
• Colonel Sanders started Kentucky Fried Chicken in his 60s

These are secular examples, but the Bible is also full of people who did their most significant work in what we'd consider the second half of life. Abraham was 75 when God called him to leave his homeland. Moses was 80 when he led the Israelites out of Egypt.

The timeline for a meaningful life is longer than our youth-obsessed culture would have us believe.

The Faith Factor: Purpose Over Performance

As a Christian, I've found that faith offers a particularly powerful reframing of accomplishment.

When Jesus talked about success, he consistently turned conventional wisdom upside down. The first shall be last. The greatest among you will be your servant. Store up treasures in heaven, not on earth.

These aren't just nice religious platitudes. They're a fundamentally different metric system for measuring a life well-lived.

If we believe we were created by God for a purpose, then "enough" accomplishment isn't defined by cultural benchmarks. It's defined by faithfulness to that purpose.

Some days, living purposefully looks impressive by worldly standards—landing the client, earning the promotion, receiving recognition.

Other days, it looks like showing patience with difficult people, choosing integrity when no one would know the difference, or serving in ways that will never make your resume.

Both matter. Both count as real accomplishment when your metric is faithfulness rather than fame or fortune.

Practical Steps: Recalibrating Your Metrics

So where do we go from here? If you're feeling the weight of "not enough accomplishment," how do you practically recalibrate your metrics? Here are some steps that have helped me:

1. Take an Honest Inventory

Grab your favorite beverage (I recommend a good bourbon), find a quiet spot, and take an honest inventory of your life. Make three lists:

• What society says I should have accomplished by now
• What I've actually accomplished (including the things that don't go on resumes)
• What would make me feel fulfilled if I accomplished it in the next 10 years

Look for the disconnects between these lists. They'll tell you a lot about where you might be using the wrong measuring sticks.

2. Identify Your "Why"

Behind every goal is a "why." We want the promotion because we believe it will bring respect. We want the bigger house because we think it represents security or success.

Get honest about your whys. Some may be perfectly valid. Others may be attempts to fill needs that achievements can't actually satisfy.

Ask yourself: "If I achieved this goal, what do I believe it would give me?" Then ask if there might be more direct routes to that same feeling or need.

3. Define Your Non-Negotiables

What are the things you're not willing to sacrifice on the altar of accomplishment? Your health? Key relationships? Your integrity? Your faith?

Write them down. Be specific. Review them regularly, especially when facing decisions where accomplishment and these values seem to conflict.

4. Find Your "Enough"

Our consumer culture thrives on the concept of "never enough." There's always a bigger house, a better job, a more impressive accomplishment just around the corner.

Contentment is counter-cultural. But it's also deeply biblical. As Paul wrote, "I have learned to be content whatever the circumstances" (Philippians 4:11).

This doesn't mean settling for less than you're capable of. It means recognizing when you have "enough" and not allowing society's constantly moving goalposts to rob you of satisfaction.

5. Celebrate Process, Not Just Results

We tend to celebrate finish lines while ignoring the race itself. But much of life's richness happens in the process, not just the outcomes.

The business that failed taught you resilience. The relationship that ended taught you about yourself. The goal you're still working toward is developing your character in ways you might not see yet.

6. Find Your People

Surround yourself with people who measure success similarly to you. If you're trying to value impact over income, connection over acquisition, faithfulness over fame—find others on the same journey.

Some of my most valuable conversations happen monthly when I meet with a few other guys my age for cigars and real talk. We challenge each other's definitions of success, remind each other what actually matters, and celebrate accomplishments the world might not recognize.

The Unseen Accomplishments

Here's something I've been thinking about lately: Some of our most significant accomplishments may be completely invisible to us.

The encouragement you gave that helped someone else keep going. The example you set that influenced someone you'll never know about. The small acts of faithfulness that created ripple effects you can't see.

As a person of faith, I believe that some of our most important impact may only be revealed in eternity. The investments in others, the quiet integrity, the faithful stewardship of whatever gifts and roles we've been given—these may be accomplishments of the highest order, even if they never earn worldly recognition.

Starting Today

If you're in that place of feeling like you haven't accomplished enough, know that you're not alone. It's practically the official sport of midlife. But also know that it's never too late to recalibrate your metrics and focus on what truly matters.

Maybe your greatest accomplishments are still ahead—not because you'll finally get that corner office or seven-figure deal, but because you'll measure your life by metrics that actually lead to lasting fulfillment.

What if your most significant achievements won't be the ones society celebrates, but the ones that align with your deepest values and purpose?

What if you're exactly where you need to be to accomplish exactly what matters most?

What if you've already accomplished more than you realize, just not in the categories the world tends to count?

These aren't just comforting questions. They're invitations to a fundamentally different way of measuring a life well-lived.

I'll be over here on my deck, cigar in hand, continuing to wrestle with them myself. Care to join me?

What metrics of success have you had to recalibrate in your own life? I'd love to hear your thoughts. Connect with me on Instagram, Facebook, X, and visit Brown's Life or check out my cigar blog at Beyond the Humidor.