Enjoy Anyway

A few weeks ago, I watched a scene unfold that hasn’t left me.

Two people—both exhausted, both under pressure—snapped at each other in a meeting. It started small: a clipped tone here, an eye roll there, a comment that landed a little too sharp. Within minutes, the room felt heavier. Shoulders tightened. People checked out. The work didn’t suddenly get harder, but it felt harder, because the people side of it got messy.

A few days later, I had a very different moment. Same company. Same pressures. Same imperfect people. But this time I watched two teammates lean in, ask clarifying questions, own their part, and laugh together on the way out the door. Nothing in our circumstances had changed. The difference was simple but profound:

In the first meeting, people were difficult… and we resented it.
In the second, people were difficult… and we extended grace anyway.

That’s when this quote from Ryan Leak’s Leveling Up grabbed hold of me:

“Life is difficult. Enjoy it anyway.
People are difficult. Enjoy them anyway.
I know we might think we need to wait for ideal circumstances and people to come around before we can start enjoying them, but ideal isn’t coming.”

That last line is the gut punch: “ideal isn’t coming.”

Most of us are waiting on some version of “ideal” before we let ourselves live with joy, extend grace, or reconnect with people we’ve drifted from. We’re waiting for:

• the perfect project
• the perfect boss or team
• the perfect customer
• the perfect health, finances, or family season

But ideal isn’t coming.

If we keep waiting for perfect circumstances and perfect people, we’ll wait our whole lives—and miss the joy that’s available in the middle of the mess.

The Ache Beneath the Surface

If we’re honest, a lot of us are tired.

Some of you are carrying heavy loads at home—health scares, aging parents, financial stress, kids struggling, marriages under strain. Others are carrying stress at work—deadlines, demanding projects, complex customers, and the weight of wanting to do excellent work every single day.

When life feels like that, it’s easier to pull back than to press in:

• We keep conversations shallow because deep ones feel risky.
• We avoid the coworker who rubs us the wrong way.
• We quietly “ghost” relationships that feel complicated.
• We scroll on our phones instead of engaging the people right in front of us.

And yet—underneath the busyness and withdrawal—there’s an ache:

We want to be known and loved as we are.
We want to feel joy again, not just grind.
We want relationships that are strong enough to survive difficulty, not just exist when everything is smooth.

We don’t need more information about how life is hard. We know that. What we need is a different way to live in a hard life.

What Our Culture Gets Wrong

American culture doesn’t help us here.

Our culture whispers (and sometimes shouts):

• “You can be happy when…” you get the promotion, upgrade the house, find the “right” people, or escape the “wrong” ones.
• “If people are difficult, write them off.” Unfollow. Unfriend. Uninvite. We trade reconciliation for cancellation.
• “If life is hard, numb out.” Binge more. Scroll more. Buy more. Anything to not feel the weight of reality.

The result? We chase a utopia that doesn’t exist—a life, a workplace, a group of people who never frustrate, disappoint, or stretch us.

But here’s the problem: the most meaningful research we have tells a different story.

An 85‑year Harvard study on adult development—one of the longest studies ever conducted—concluded that positive relationships are the single strongest predictor of long‑term happiness and health, more than career achievement, money, exercise, or diet.

At the same time, we pour huge amounts of our attention into things that don’t deepen relationships or joy. You know the average person spends hours a day on screens, primarily consuming entertainment. Our screen-time habits make it easy to escape life, but harder to enjoy real people in real time.

Our culture trains us to:

• avoid discomfort,
• curate our image, and
• chase circumstances we can’t control,

instead of learning to enjoy an imperfect life with imperfect people… right now.

Enjoy Anyway: Three Shifts

So how do we actually live Ryan Leak’s advice inside the real world of business, families, and everyday pressures?

I see three shifts we can make—starting this month.

1. Extend Grace to Imperfect People

Everyone you meet today is fighting a battle you can’t see.

That teammate who snapped at you might be running on two hours of sleep because of a sick child. The coworker who seems distracted might be waiting on a medical test result. The person who is “always negative” may be carrying a weight they’ve never named out loud.

Grace doesn’t mean we ignore problems or avoid hard conversations. It means we start with generosity instead of suspicion.

Before you assume the worst, ask yourself:

• “What else might be going on with them?”
• “If I knew their whole story today, how would I respond differently?”

In previous messages we’ve talked about refusing to let mistakes or failures define us as people. In the same way, let’s refuse to let a frustrating moment define someone else in our own minds. Grace says, “I see your humanity. I know you’re more than your worst day.”

2. Move Toward People You’ve Avoided

If we’re honest, most of us can name at least one person we’ve quietly stepped away from:

• a coworker we had tension with,
• a former teammate we just “lost touch” with,
• a friend or family member we now keep at arm’s length.

Distance feels safer than dealing with discomfort. But distance also starves us of the deep relationships we were made for.

We’ve shared before about that Harvard study and other research that points to the same conclusion: relationships are not a “nice to have;” they are core to a healthy, meaningful life.

So here’s a challenge:

Before this month ends, reach out to one person you’ve been avoiding.

You don’t have to fix everything in one conversation. You don’t have to agree on all the details. You simply have to move toward instead of away. A text. A coffee. An honest, humble, “Hey, I miss you. Can we talk?”

You might be surprised how much relief and joy that small step creates—for them and for you.

3. Practice Joy in the Middle of Difficulty

Joy isn’t the same as denial.

Joy doesn’t pretend life is easy. It doesn’t ignore real grief, stress, or injustice. Joy looks directly at difficulty and says, “Even here, there is something good, and I refuse to let the hard parts blind me to it.”

In past newsletters, we’ve talked about the power of celebration—how intentionally noticing goodness helps us endure trials with a steadier heart. The same principle applies here.

Practicing joy can be as simple as:

• Naming gifts in the middle of stress. Stuck in traffic? You still have a job to drive to and a company full of people who care about you.
• Looking for what’s right, not just what’s wrong. The project may be behind, but your team showed up early and stayed late. That matters.
• Letting laughter in. Joy and humor don’t trivialize work; they fuel it.

Life is difficult. But difficulty doesn’t get the final word unless we hand it the microphone.

Stop Chasing a Utopia That Doesn’t Exist

Let’s say it plainly: there is no perfect company, perfect family, or perfect life.

• At work, we will disappoint each other sometimes. We’ll miscommunicate. We’ll miss deadlines. We’ll make mistakes.
• At home, there will be seasons where money is tight, health is fragile, and relationships are strained.
• In your own heart, there will be days when you don’t feel strong, motivated, or “on.”

Utopia isn’t coming.

But something better can grow: a community where people tell the truth, own their part, extend grace quickly, repair relationships when they’re strained, and keep choosing joy even when nothing is tidy.  Our job now is not to wait for “ideal” to finally arrive. Our job is to live differently in the middle of non‑ideal.

Putting This Into Practice

I don’t want this to be just another encouraging message you read and forget. Here are some very practical ways to “enjoy anyway” this month:

1. 24‑Hour Grace Challenge
   For one day, assume good intent from every person you interact with. When someone frustrates you, ask one clarifying question before you form a judgment.
2. Reach Out to One Person You’ve Avoided
   Make a list of names you’ve drifted from or quietly avoided. Circle one. Send a message today:
   1. “You’ve been on my mind. How are you really doing?”
   1. “I know things got awkward. I’d love to reconnect if you’re open to it.”
3. Joy in the Middle, Not After the Fact
   At the end of each workday this week, write down:
   1. One thing that was difficult.
   1. One thing that was good in the middle of that difficulty.

This trains your eyes to see joy without waiting for the hard thing to disappear.

• Practice “Small Courage” at Work
  Step toward someone instead of away:
  • Invite a newer teammate to lunch.
  • Thank someone specifically for how they showed up on a tough day.
  • Apologize quickly when you realize you were short or harsh.
• Build a Simple Rhythm of Celebration at Home
  Once a week, around the dinner table or in a quiet moment, ask: “Where did we see something good this week, even though life is hard?” You’ll be amazed at what surfaces over time.

Life is difficult. People are difficult. That’s not a sign that something has gone wrong; it’s a sign that we live in the real world.

What will set us apar is not that we escape difficulty or finally find the “perfect” situation. What will set us apart is that we choose to enjoy anyway:

• to extend grace rather than withdraw,
• to move toward people rather than away,
• to practice joy in the middle of the mess,
• to stop waiting on a utopia that isn’t coming.

My hope for us this month is simple:

That we become people who don’t need perfect circumstances or perfect people to live with joy, courage, and connection.

Life is difficult. Enjoy it anyway.
People are difficult. Enjoy them anyway.
Ideal isn’t coming—
but joy can, starting with us.

PGRIT,

Shaun