The Road You Can Live With

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Rewind thirteen years…

Elsewhere here in Leadership Masterworks, I have an earlier post about my oldest son. When he was four, he once watched me repeatedly push on a store door that would not open, despite the fact that the instructions were right in front of me. After I finally realized I was supposed to pull, he looked me straight in the face and delivered one of the most concise leadership assessments I have ever received: “Real stupid, Daddy. Real stupid.”

Thirteen years later, my little leadership consultant was seventeen.

One day he came to me and said, “Dad, can we talk?”

“Sure.”

“I want to change majors.”

Now, I need to give you a little context before you decide whether this was a perfectly reasonable conversation or evidence that my son had temporarily lost his mind. He had just completed his seventh semester of college studying Computer Management—what we would largely call Information Technology today.

Seven semesters.

As in: one semester away from a bachelor’s degree.

So when your seventeen-year-old son, who is approximately four months from completing the degree he has spent several years pursuing, says, “I want to change majors,” there are several perfectly reasonable parental responses available.

Mine was, “What are you thinking?”

“I want to switch to a music major.”

Now some of you are thinking, What, is he crazy?

But this wasn’t quite as crazy as it sounds. I was a musician. We had a recording studio in our home. My son had been playing piano since he was about ten. He was a very good musician, was learning songwriting, and was becoming a singer. Music wasn’t some new fascination that had appeared Tuesday afternoon because he’d watched a particularly inspiring music video.

And I understood the attraction. I had gone to music college myself. My study was in jazz music performance. Saxophone. I had spent years practicing, performing, studying theory, arranging, improvising—all of it.

So there was nothing foreign about this conversation.

Still.

Seven semesters. One to go.

“Why do you want to do that?” I asked.

And then came the sentence.

“Because I don’t want to be like you.”

Ouch.

“What do you mean?” I said, keeping my composure. Mostly.

“Well, you went to music college and came out and got a job as a marketing guy.”

He wasn’t wrong. I did have a minor in marketing, and that road eventually became my career.

Then he explained himself.

“I don’t want to pursue my love only to do something else. If I don’t try to do what I love, I don’t think I will be able to forgive myself. And if it doesn’t work out, then I can always do the other thing.”

And there it was. Not rebellion. Not adolescent foolishness. Not even, as I came to understand it, an argument for following your passion.

It was something much more interesting.

He had decided which unanswered question he was willing to live with—and which one he wasn’t.

So off he went to Berklee College of Music in Boston.

This Is Not a “Follow Your Passion” Story

We need to get this out of the way early because follow your passion has become one of those phrases that can mean almost anything.

Sometimes it is wise counsel. Sometimes it is terrible counsel wearing an inspirational T-shirt.

Loving something does not mean you are good at it. Being good at something does not necessarily mean people will pay you to do it. Wanting something intensely does not obligate reality to cooperate. And feeling excited about a new direction does not automatically mean God is leading you there.

Passion is valuable. It is not sovereign.

I have watched people make enormously unwise decisions because they confused desire with calling, enthusiasm with ability, and dissatisfaction with divine direction. “I need to follow my passion” can become a remarkably spiritual-sounding way of saying, I would rather do what I enjoy than faithfully do what is required of me.

That was not what was happening here.

My son had history behind this idea. He had years of practice behind it. He had demonstrated ability. He had written, played, sung, learned, experimented, and lived around music long enough to know this was not merely a passing attraction. There was evidence beneath the desire.

He also understood that failure was survivable. If music did not become a sustainable road, another road still existed. It might be disappointing. It might cost him time. It might require another turn later. But failure would not destroy him.

And he was not making the decision in isolation. He came to talk with his father—a man who had actually studied music, lived in that world, and then eventually taken another professional road.

History. Ability. Evidence. Recoverability. Counsel.

Those things do not guarantee that a decision is right, but they do help distinguish a considered risk from an impulse.

This was not fantasy.

It was possibility.

And there is an enormous difference.

Seven Semesters Are Heavy—but They Are Not Sovereign Either

There is a concept from economics and decision-making called the sunk-cost effect. A sunk cost is something you have already spent and cannot recover—time, money, effort, energy. The effect occurs when what we have already invested begins exerting more influence over the next decision than it should, even when what we now know suggests another direction may be wiser.

Seven semesters is a substantial sunk cost.

But calling something a sunk cost does not mean it was wasted.

Those semesters had value. He had learned. He had matured. He had developed discipline. He had gained knowledge, experience, and capability. Changing direction did not somehow erase what had already been gained.

The problem comes when yesterday’s investment is given veto power over tomorrow’s decision.

Past investment may have continuing value without having controlling authority over the future.

That distinction matters because “You’ve come this far,” “You’re almost finished,” and “Don’t waste all that work” are not foolish statements. Sometimes they are exactly right. There is great virtue in perseverance, and our culture is not exactly suffering from an epidemic of excessive faithfulness and follow-through.

There are times when you need to finish what you started because finishing is the faithful thing to do.

But perseverance is not the same thing as wisdom.

If you discover that you’re traveling toward the wrong destination, the distance you’ve already traveled is not necessarily an argument for continuing.

Sometimes it is simply the distance you traveled before you finally saw more clearly.

We can become so committed to defending yesterday’s decision that we stop asking whether it remains today’s wisest one.

That is not perseverance.

That is stubbornness with a résumé.

Some Decisions Are Not Between Right and Wrong

We often talk about discernment as though life’s important decisions arrive conveniently labeled RIGHT and WRONG, GOD’S WILL and NOT GOD’S WILL, WISE and FOOLISH.

Occasionally they do.

But some of the hardest decisions in life are difficult precisely because both roads are legitimate roads.

There was nothing wrong with Computer Management. There was nothing inherently virtuous about music. My son wasn’t choosing righteousness over sin. He wasn’t leaving some morally compromised life to pursue a noble calling.

Two roads stood in front of him, and both could have become a life.

That is where discernment gets harder.

Scripture says, “A man’s heart plans his course, but the LORD determines his steps” (Proverbs 16:9 BSB). That does not eliminate planning. It puts planning in its proper place.

We plan. We investigate. We seek counsel. We count the cost. We look honestly at our abilities, responsibilities, motives, opportunities, and limitations. Then we make a decision while remembering that we are creatures, not the Author of the story.

“There are many plans in a man’s heart, but the purpose of the LORD will prevail” (Proverbs 19:21 BSB).

That should make us neither passive nor frightened.

It should make us humble.

The Road Less Traveled Is Not Automatically the Right Road

Robert Frost’s The Road Not Taken has become one of our favorite cultural encouragements to be unconventional: take the road less traveled, be different, do what others won’t do.

That is not quite what the poem says, and it certainly isn’t a biblical principle.

Sometimes the road everybody is taking is popular because it is foolish. Sometimes it is popular because it is wise. Sometimes the strange, adventurous, lonely road is the courageous one. Sometimes it is simply the stupid one.

There is nothing inherently righteous about choosing the road fewer people choose.

The point is not to be unconventional.

The point is to be faithful.

Frost’s traveler himself admits that the two roads had been worn “really about the same.” The decision wasn’t between an obvious road and a heroic one. It was between two possible roads, and he could not travel both.

That is precisely what makes the poem fit here.

My son’s decision wasn’t between the safe road and the courageous road.

It was between this road and that road.

Both were real. Both had possibilities. Both carried costs.

And he could not live both lives.

Every Meaningful Yes Contains a No

That may be one of the hardest truths about adult decision-making: every meaningful yes contains a no.

Choose one career and you do not simultaneously live the career you declined. Marry one person and you surrender every life that might have unfolded with someone else. Move to one city and another becomes the city where you did not live. Take one opportunity and there are other opportunities you cannot take.

Stay—and you relinquish whatever leaving might have produced. Leave—and you relinquish whatever staying might have become.

This is one reason important choices carry weight even when both choices are good. We are not merely choosing something. We are also relinquishing something else.

And that relinquishment is one reason we long for certainty before making important decisions.

We would like God to show us both roads all the way to the end, let us inspect the outcomes, and then allow us to walk backward to the fork and choose.

He rarely does.

Instead, we are given enough light for faithfulness and not enough light for omniscience.

So eventually we choose.

And the other road becomes the road we did not take.

Wisdom Counts the Cost

Jesus once asked, “Which of you, wishing to build a tower, does not first sit down and count the cost to see if he has the resources to complete it?” (Luke 14:28 BSB).

That is wisdom.

Before you change careers, leave a position, launch a company, enter ministry, relocate your family, change majors, or make any other consequential decision, sit down first.

Count the cost.

What responsibilities do you already carry? Who else will bear the consequences of your decision? Do you have evidence that you can do what you are considering? Have people who know you well confirmed the ability you believe you possess? Is the opportunity real or merely imagined? Are you running toward something worthy, or merely running away from something difficult? Can you afford to fail? If you fail, what happens next?

And perhaps one of the most important questions: What do wise people who are not emotionally invested in your preferred answer think?

“Plans fail for lack of counsel, but with many advisers they succeed” (Proverbs 15:22 BSB).

Those questions are not designed to kill courage.

They are designed to distinguish courage from impulse.

But You Can Count the Cost Forever

There is another side to this.

You can investigate forever. You can seek one more opinion, read one more book, build one more spreadsheet, take one more assessment, run one more scenario, and wait for one more sign.

Eventually analysis can stop being wisdom and become avoidance.

Ecclesiastes says, “He who watches the wind will fail to sow, and he who observes the clouds will fail to reap” (Ecclesiastes 11:4 BSB).

The farmer waiting for conditions to become risk-free will never plant anything.

There is always wind. There are always clouds. There is always something you cannot know.

That means there is a point at which good decision-making requires you to stop gathering information and act on the information you have.

My son could have spent another ten years wondering whether music might have been his road. No amount of further analysis could have answered that question.

There was only one way to know what would happen if he tried.

He had to try.

There Are Questions Thinking Cannot Answer

I spend a great deal of time encouraging people to think before they act.

Please do.

Wisdom asks questions, seeks counsel, looks farther down the road than today’s emotion, and counts the cost.

But there are questions thinking cannot answer.

You can study swimming for years without discovering what deep water feels like. You can analyze entrepreneurship without discovering whether you can build a company. You can read about leadership without discovering how you will respond when people actually depend upon you. And you can imagine a life in music without ever discovering what that life would actually require of you.

There comes a point when possibility has to meet reality.

That is not an argument for recklessness. It is an argument against pretending that thinking alone can eliminate uncertainty.

It cannot.

Sometimes the responsible thing is to stay. Sometimes the responsible thing is to go.

Wisdom is learning to know the difference.

Regret Is Not a Compass—but It Can Be Evidence

His statement has stayed with me all these years:

“If I don’t try to do what I love, I don’t think I will be able to forgive myself. And if it doesn’t work out, then I can always do the other thing.”

I want to handle that carefully.

Regret is not a compass—but it can be evidence.

If avoiding future regret becomes the governing principle of our decisions, we can rationalize almost anything. We do not obey every longing simply because we fear wondering later what might have happened.

But regret can expose something. It can reveal what we know about the relative weight of two possible outcomes.

My son was not claiming that music would work.

He was accepting the possibility that it might not.

He had simply concluded that trying and failing was a consequence he could live with, while never trying at all was a question he did not want to carry for the rest of his life.

That gives us a better question than, Which choice will keep me from ever regretting anything?

There is no such road.

A better question is: Which consequence am I prepared to carry faithfully?

Sometimes one possible regret is recoverable while another becomes permanent.

His reasoning was essentially this: If I try music and discover that I cannot make a life of it, I can change direction. If I never try, I may spend the rest of my life wondering.

He knew which uncertainty he could live with.

“Because I Don’t Want to Be Like You”

Then there was that other sentence.

“Because I don’t want to be like you.”

There are several ways a father can hear that.

One of them is badly.

I could have defended myself. I could have explained that my career had not been some tragic consolation prize. I could have reminded him that music had remained an important part of my life. I could have pulled rank, and I certainly could have played the Seven Semesters Card.

But perhaps the most dangerous thing I could have done would have been to make his decision about me.

My ego was not evidence.

His choosing differently from me did not make my choices wrong.

Our children are not required to vindicate our decisions by repeating them.

Neither are the people we lead.

One of the quiet temptations of leadership is to reproduce ourselves instead of developing people. I succeeded this way, therefore you should go this way. I learned this lesson in this sequence, therefore you should learn it in the same sequence. I chose this road, therefore choosing another one is criticism of mine.

No.

Good leadership is not producing smaller copies of ourselves. It is helping people become wise enough, mature enough, self-aware enough, and responsible enough to make faithful decisions when we are not there to make them for them.

And somewhere in that conversation I had to recognize something almost embarrassingly simple:

If I had spent seventeen years teaching him to think, I could hardly punish him now for thinking.

Your Life May Become Someone Else’s Wisdom

My son had looked at my life and learned something from it.

That did not make my road wrong.

It meant my road had become part of the information available to him as he chose his.

There is something deeply satisfying about that now.

A life does not have to be imitated to have taught something valuable.

Sometimes your experience becomes another person’s encouragement. Sometimes it becomes their warning. Sometimes it simply shows them what one road looks like so they can decide whether that road is theirs.

All three can be forms of stewardship.

As leaders, parents, coaches, mentors, and friends, we have to become comfortable with the possibility that some of the people we influence most deeply may honor what we taught them by making a choice we would not have made.

That is not necessarily failure.

Sometimes it is evidence that they learned to think.

Leadership Sometimes Means Letting Someone Choose Differently

I was still his father. I knew more than he did about certain things. I had more life experience. I knew something about music as a profession that he could not yet fully know.

And I had every parental instinct available to say, Finish the degree.

That might even have been reasonable.

But there comes a point in developing another human being when leadership has to loosen its grip.

If we have spent years trying to teach someone how to think, eventually we have to allow them to think. If we have tried to develop judgment, eventually we have to allow them to exercise judgment. If we have taught responsibility, eventually they must carry responsibility for a decision whose outcome we cannot control.

Otherwise we have not developed maturity.

We have developed dependence.

That does not mean we stop counseling. It does not mean we become indifferent. It certainly does not mean every youthful idea gets funded and applauded.

It means there comes a moment when love must make room for agency.

And sometimes the sentence that tells you your child is becoming his own man is not, “Dad, I want to be just like you.”

Sometimes it is, “Dad, I don’t want to be like you.”

Ouch.

Still.

That may be exactly the sentence you have spent seventeen years preparing him to be able to say.

And So He Went

And so off to Berklee College of Music in Boston he went.

He did well.

He had some remarkable experiences in music.

And what strikes me now is that the value of the decision cannot finally be measured merely by whether music became the permanent road.

We make a mistake when we evaluate every decision only by its eventual destination. Some roads teach us. Some expose us. Some develop abilities we later use somewhere completely unexpected. Some introduce us to people who alter our lives. Some eliminate illusions. Some give us confidence. Some humble us.

And some simply answer a question that needed to be answered.

Occasionally a road’s great gift is that, years later, we no longer have to wonder what might have happened had we taken it.

Faithfulness at the Fork

I am increasingly convinced that faithful stewardship is not about finding a life in which every major decision becomes obvious.

God has not promised us that.

He has given us truth, wisdom, people from whom to seek counsel, minds with which to think, abilities to develop, responsibilities to honor, opportunities to evaluate, and providence that remains His even when the road ahead disappears around a bend.

James warns us against speaking arrogantly about tomorrow—as though we possess it. We are to say, in substance, if the Lord wills, we will live and do this or that (James 4:13–15).

That is not timidity.

That is creaturely confidence—the freedom to act faithfully while remembering that God remains God and we do not.

We make the wisest choice we can before Him.

Then we walk.

And perhaps that is the deeper lesson my seventeen-year-old was teaching his father thirteen years after his first rather memorable consultation.

At four, he taught me that pushing harder is not always the answer.

At seventeen, he taught me that continuing down the same road is not always the answer either.

Sometimes faithfulness is persistence. Sometimes faithfulness is changing direction. And sometimes you stand at a fork knowing that you cannot travel both roads, cannot see around either bend, cannot guarantee the outcome, and cannot remain standing there forever.

So you listen. You pray. You think. You count the cost. You tell yourself the truth. You seek counsel. You ask whether the road before you is supported by evidence or merely emotion, whether its risks are faithful or foolish, whether its consequences are yours to bear or will be imposed upon others, and whether fear has quietly begun calling itself wisdom.

Then you choose.

And you walk.

“Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.”

— Robert Frost, The Road Not Taken

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Coaching Questions

[The purpose of these questions is not merely to evaluate what you know, but to help you examine how these truths are showing up in your life and leadership. Take your time with them. Resist the temptation to answer quickly or to think primarily about someone else who needs to hear this. Ask the Lord to help you see yourself clearly, invite someone you trust to speak honestly into your life, and identify where knowledge needs to become action. Applied knowledge repeated consistently becomes transformation.]

1. Is there an area of your life where yesterday’s investment is exerting more influence over today’s decision than present reality should allow? What value did that investment genuinely produce, and what would you decide now if you did not feel obligated to defend the decision that originally produced it?
2. Are you facing a genuine right-versus-wrong decision, or two legitimate roads that require wisdom rather than certainty? What do history, demonstrated ability, evidence, wise counsel, responsibility, consequences, and recoverability tell you about the choice?
3. Is there something you have wanted to attempt for years that you have never honestly tested? Is your restraint faithful stewardship, or has fear gradually learned to call itself wisdom? At what point would further analysis simply become avoidance?
4. If you lead, parent, mentor, or develop others, can they choose differently from you without experiencing your disappointment as punishment? Are you forming wise people capable of making faithful decisions, or merely people who have learned which decisions will please you?
5. Looking honestly at the fork before you, which consequence could you carry more faithfully: trying and discovering that the road was not yours, or never trying and carrying the unanswered question with you? What would it look like to submit that choice to the Lord, seek wise counsel, count the cost, and then actually choose?

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The Road Not Taken

Robert Frost

Two roads diverged in a yellow wood,
And sorry I could not travel both
And be one traveler, long I stood
And looked down one as far as I could
To where it bent in the undergrowth;

Then took the other, as just as fair,
And having perhaps the better claim,
Because it was grassy and wanted wear;
Though as for that the passing there
Had worn them really about the same,

And both that morning equally lay
In leaves no step had trodden black.
Oh, I kept the first for another day!
Yet knowing how way leads on to way,
I doubted if I should ever come back.

I shall be telling this with a sigh
Somewhere ages and ages hence:
Two roads diverged in a wood, and I—
I took the one less traveled by,
And that has made all the difference.

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