Wouldn’t It Be Great If…? (Season 2021, Episode 5)

I stare out the window. The trees have dropped all their leaves. Fall fell. Now it’s winter. But I’m in north-central Texas so that isn’t quite what it is to you guys who live in Canada or Minnesota or Maine. I’m craving a change of scenery. Not just the kind nature provides, but the kind that puts your head into a clearer space. 

So away we go to a spot we often frequent. About half-a-day away by car. Not bad.

Piney woods. They affect me in the most positive way.

Here I am sitting on the covered back porch with an overhead radiant heater. It’s chilly, but I’m comfortable. I’m staring at a golf course, the 6th hole. I’ve got a clear shot of the tee boxes and the green. Almost a straight-on view, which allows me to track the balls the golfers hit from the tee.

I’ve been here before. Back in the summer when I didn’t need a heater. Or flannel shirts.

It was then, during the summer, when I told my wife, “I could spend quite a lot of time here.” She immediately responded, “Yeah, I could, too.”

Then we engaged those dreaming wheels in our heads. They’re not really just dreaming wheels though. They’re more like pondering wheels looking for a path forward, working out a way to make it happen!

You daydream. Imagining what it might be like to be in your favorite place. Maybe a beach. Maybe mountains. Maybe lakeside. Your mind drifts to your life and where you’re at versus where you’d most like to be. Some success that isn’t reality. Yet. Some achievement that’s unrealized. Some lifestyles you don’t currently enjoy. You ask yourself the same question you’ve asked most of your life.

Wouldn’t it be great if…?

Wouldn’t it be great if we had a lake house?

Wouldn’t it be great if our business were twice as big?

Wouldn’t it be great if we got a new car?

Wouldn’t it be great if we got married?

It’s a question we ask ourselves about anything and everything. Like a can of lighter fluid on our wildest dreams, we engage parts of our brain that feel like we’ve neglected for too long. We easily embrace it and go with the flow of imagining what life might be like if our hypothetical were real.

Wouldn’t it be great if…? 

You’ll never say, “No, it wouldn’t be great.”

Your mind will always think, “Yes. Yes, it would be great.”

Because during such times, in our head we work things out so everything works out beautifully. No snags. No problems. No downsides.

We do the same thing with the choices we didn’t make but wish we would have. We assume the choice we didn’t make would have worked out marvelously. We never think, “Good thing I didn’t take that other path ’cause that would have been a disaster!”

In our heads, the choice we didn’t make would have worked out fine. Or perfectly fine. Or terrifically.

We look back and think, “What if we’d made that other choice?” Again, in our heads, we iron out all the outcomes so they’re better than the ones we now enjoy.

The reality is we only know the outcomes of the choices we made. Had we made a different choice…we think we know how it would have worked out, but we don’t really know. We project a successful outcome in our minds. It feels real prompting us to regret the choice we made. Maybe. Or at the least, wondering if the other choices might have been better!

Fact is – maybe it would be great. Maybe it would be a disaster. Maybe it wouldn’t matter. We’ll only know if we pursue it.

So it makes sense that our brains would gravitate to the best-case-scenario. Why not think the best? Why not think, “Wouldn’t it be great if (fill in the blank)?” That’s better than thinking, “Wouldn’t it be awful if (fill in the blank)?”

I’m still sitting there looking out over a golf course with piney woods across the way. Chipmunks, squirrels and small birds are scurrying about in the morning cold foraging for food. I’m pondering life and they’re trying to sustain life. No thought about tomorrow. They’re not even bothered by later today. Talk about a lesson of being present…in the present!

Here’s what I’m not thinking or saying, “Wouldn’t it be awful if we had a place like this?”

People would think I’m the King of Pessimism if that were the case. I realize some people have such a dour outlook on life they may lean toward always thinking the worst, but I suspect even the most pessimistic people dream about the ideal outcome. I sure hope they do.

It’s a real gift and blessing that we’re able to see and feel what great success might be like. No guarantees we’ll achieve it, but those thoughts surely inspire us, don’t they?

For the past few years, I’ve regularly watched this video of a Scottish busker named Natasha Cook Jenkins. She began busking – playing music on the street – when she was 12. She’s now 20, but when she was 17 a record producer noticed her. Her persistence got her into the Institute of Contemporary Arts in London, where she lives today. I watch this video more regularly than many busking videos because the camera shows us what she sees while performing. Not many people. Other busking videos most frequently show folks just going about their daily lives oblivious to the craft happening as they pass by. Having never done it myself, I can only imagine the emotional roller coaster of doing what you love only to be ignored. Or worse. I think one reason I so love busking – and have since I was a teen – is because of the courage and determination it requires. And the optimism of the performers. Optimism that they’ll make a few bucks. Optimism that people will notice. Optimism that they’ll get some positive attention that may lead to something more stable and better.

The most famous busker has to be Ed Sheeran. And doesn’t it show when you watch him perform? He confesses that he learned showmanship by busking, trying to get people’s attention and keep it.

From the streets and subways to Wembly Stadium, he’s proof that extraordinary talent and stone-cold determination can result in something insanely successful. Now, I just need extraordinary talent and stone-cold determination. 😀

Wouldn’t that be great? OF COURSE.

In a documentary, Ed Sheeran: In My Own Words, he puts a focus where you may not expect.

Indeed you have to work at it. Persistence. “You give yourself no choice but to get better.”

Let’s focus on what Ed said about getting better! I’m thinking about that because the other day I heard a girl say she most wanted to be “social media famous.” It sparked the “what if” question. “What if you were social media famous?”

Would that be you getting better? Maybe. Maybe not.

Hulu has an ABC News documentary on Only Fans, a social media website made famous by porn stars. It’s touted as the X rated version of Instagram. Some of us think quite a lot of Instagram is already pornographic. But no matter your point of view about such things, “better” is too subjective and relative for many people. Better for whom? That’s often asked.

Maybe you get up at 5 am every morning to go grind away at a very physically hard job for modest pay. In 2019 the median income for an American worker was just over $31,000. In 2020 the majority of American households earned less than $70,000. Mostly people putting in the time to earn their paychecks. Doing work worth being paid for, but not likely too glamorous. Mostly mundane. Average. In every way.

A woman desiring to be an “influencer” can focus on the fame and money and wonder, “What if I were a major Instagram influencer?”

Nobody knows her name. Or face. Or body. So enter Only Fans, a platform where she can become a “sex worker,” by taking off her clothes and having ordinary “fans” subscribe by paying a monthly amount. She’ll get to keep 80% of the money while the platform keeps the remaining 20%. So she begins to take nude photos of herself. And some videos, too. She’s gonna be a big star. Make lots of money.

Is she getting better?

No. She’s giving herself options other than making herself better.

She’s contributing to the worse of humanity. The selfish, vanity that can carry any of us into a pit from which we may never recover. Worse yet, she’s contributing to helping others fall into the same pit of despair and disgrace. And she’ll argue – like modern culture always does – that it’s her right and she’s not going to hear anybody who dares make a judgment about her chosen path. Indeed, she has the right – I dare say the OPPORTUNITY – to either contribute to the good of herself and the world or to contribute to the damage to herself and the world. She’s choosing the latter, not the former. The more she argues about the good she’s doing the more I’m made to realize and understand how low humans can go in self-delusion. Sad.

Sadder still is the question, “Wouldn’t it be great if porn didn’t exist?”

Wouldn’t it be great if humanity behaved with more pride, dignity, and moral goodness?

Wouldn’t it be great if we collectively – and individually – did our very best every single day?

Wouldn’t it be great if we could trust each other for help, support, and encouragement?

Wouldn’t it be great if hubris weren’t so prevalent in the world?

Wouldn’t it be great?

Wouldn’t it be great if we realized God is God and we’re not?

Wouldn’t it be great if broken people could be put back together?

Wouldn’t it be great if we found joy in the help we provided others today?

Wouldn’t it be great if the pursuit of usefulness was more important than the pursuit of money or fame?

As I was preparing today’s show my headphones were playing lots of tunes. Mostly, Tom Petty’s Wildflowers & All The Rest. We lost Tom back in October 2017. Years ago when I was in the record business I remember his 1979 big breakthrough with the album, Damn The Torpedos. He and the Heartbreakers became synonymous with guitar-based storytelling. And I think, “Wouldn’t it be great if Tom was still alive making music?”

I hit play on The Caution Horses by Cowboy Junkies.

Listening to Margo Timmins, the lead female singer, makes me feel…warm. And it’s cold outside. In fact, we may be setting records here in DFW. Just days ago we had a horrible 100 car pile-up that killed 6 due to black ice on the roads. The kind of ice you can’t see. Single-digit temps aren’t common ’round here.

And I think, “Wouldn’t it be great if that wreck hadn’t happened?” It wrecked more than cars and trucks. This weekend lots of families were wrecked by a thin sheet of ice on the highway.

Some “wouldn’t it be great if” questions have obvious answers. Others, not so much.

Wouldn’t it be great if that were true?

Oh, wait a minute. It is.

And that’s worth considering more deeply. Wouldn’t it be great if you were just one decision away from fixing something? Forget trying to fix everything. How ’bout we focus on fixing something – maybe THE most important something?

The day job is helping leaders at the most personal level. It’s not just professional. It’s personal, often delving into their private lives as they confide challenges and obstacles they’d like help figuring out. The work is therapeutic. Always. Because it’s safe, supportive, and encouraging. It’s common for the process to involve many discussions about decisions because the work is transformational. My clients are high performers. Slackards don’t invest in this kind of work. Neither do bosses invest in slackards. Funny how that works.

Well, in work that transforms, people want to fix what ails them. It starts with one thing. I don’t think any client has ever said to me, “I’d like to fix this, and that, then this other thing, and oh yeah, then these 5 other things.” High achievers are more focused than that. They’re capable of being preoccupied with a single thing at a time and usually the most important thing – at least, the most important thing to them.

What if a single decision – one decision – could make a GREAT difference?

You already know that it’s possible because it’s already happened to you. You’ve made a decision that had a great impact on your life. You’ve likely made a number of them. I know I have.

Just shortly after I turned 18 I asked a girl out on a date. I never dated another girl. Not quite 3 years later we married. But it didn’t last.

Our youth.

Our marriage has lasted over 43 years. We’re still very in love.

Who knew that a single decision to ask a girl on a date would completely change my life? Who knew that decision would be among the single greatest decisions I ever made?

What decisions have you made that changed one thing…or everything?

Wouldn’t it be great if we knew in advance? Maybe not. The weight of the decision might paralyze us.

Wouldn’t it be great if – in just 3 months – people outside our inner circle noticed improvements (changes) in our appearance, behavior, and performance?

It would be great if we could find the path forward. A path to becoming better. And I don’t mean better looking, or more fit, or more well-off financially – although all of those would be pretty terrific. I mean, we really became better people. I mean wouldn’t it be great if we behaved better? But of course, that’s only possible if we can somehow find a path forward to thinking better. I’m not talking about improving our smartness. Or elevating our IQ. I mean wouldn’t it be great if we thought it was worthwhile to behave with greater moral integrity, enough humility to recognize God, enough dedication to put in the work to improve our character.

I know, I know. Dream on, right?

Jordan Peterson (I’m a longtime fan) observes and admonishes, You need to think through how your life could be properly arranged IF you had abilities you may now lack?

Peterson is a smart, studied, insightful man. He declares that if we make that our goal and move toward it, then we’ll move closer to it. Things inevitably get better when we do that. And it’s not about happiness. It’s about meaning. It’s about transforming into a better person. And it’s difficult. Hard. But we mostly love it because we’re wired for it.

Why then do people chase happiness or security in sameness? Why are some people so resistant to change? Fear. We get scared. Even in our difficulties. It’s that “devil we know” versus the one we don’t. We probably too often presume the devil we know must be better than the one we don’t. I suspect we’re mostly wrong about that though. We may be guilty of making an invalid comparison between two devils without considering that we could choose an angel over a devil.

What I love about the “wouldn’t it be great if” question is the optimism.

Nobody says, “Wouldn’t it be great if things didn’t work out?” The fact that we’re considering something that would be great means we’re thinking of an ideal outcome. And you know how fond I am of the ideal outcome!

Nobody answers, “No, that wouldn’t be great.” At least not to ourselves if we’re asking the question. Others might. They may not share our view or our ideal outcome. Stands to reason. It’s OUR ideal outcome, not theirs.

What are you thinking right now? What are your “wouldn’t it be great if” questions?

This past week was quite typical for me in that I had a number of conversations with people who were facing difficulties and challenges. It wasn’t unusual in that regard, nor was it unusual for them to share those with me. After all, it’s what I do. More accurately, it’s who I am. But in preparing for this episode I reflected on the nature of the challenges.









Problems from A to Z. Problems in their own lives. Problems in making choices about what they should do. Problems in helping others figure out choices.

Sometimes in my professional coaching practice, I’ll ask a client to craft a “wouldn’t it be great if” question – a question aimed squarely at their challenge. There’s power in the singularity of the question, but what comes next is where the real power is found. Answer the “how” of the question. I assume the direct answer to the question is, “Yes, it would be great” or else we wouldn’t be asking the question.

“Wouldn’t it be great if we won $1 million dollars?”

Sure. But we’re powerless to influence how. So it’s just a dream-like, fantasy-filled question. Meaningless. Well, not exactly. It’s quite meaningful actually because it fosters covetousness, which always damages us when the aim of it is self-indulgence. Let’s covet wisdom, compassion, integrity, and other qualities that can make us better.

So we answer, “Yes, it would be great” if our ideal outcome were achieved. But how?

There’s the rub.

General George Patton lived by one motto:

Always take the offensive. Never dig in.

In war and life, he always pursued forward progress. Standing still was unacceptable. The pursuit of the ideal outcome meant a degree of constant dissatisfaction. Complacency was his enemy. It should be ours, too.

What if we were to take the offensive in achieving our “wouldn’t it be great if” dreams? What if we figured out how? Then committed ourselves to it?

Experience has taught me the power of sticking with it long enough in order to figure it out more clearly. Almost never is success fast. Certainly hardly ever instant. Frequently our first “how” strategies prove incorrect. Maybe only slightly. Maybe a lot. So we adjust. We keep aiming at our ideal outcome, but our first few steps don’t end up taking us exactly where we planned. So we move a bit. And see what happens. If we see, feel, or sense progress – advancement, forward movement – then we’re encouraged to continue to push on. Maybe to push even harder now that we know things are improving.

Setting the noble goal and pushing toward it makes things – makes us – better!

Boring is digging in. Not advancing. Taking no chances. Pursuing nothing difficult.

“Wouldn’t it be great if…?”

The moment. The power of the moment.

“Until one is committed, there is hesitancy, the chance to draw back, always ineffectiveness. Concerning all acts of initiative and creation, there is one elementary truth the ignorance of which kills countless ideas and splendid plans: that the moment one definitely commits oneself, then providence moves too.

All sorts of things occur to help one that would never otherwise have occurred. A whole stream of events issues from the decision, raising in one’s favour all manner of unforeseen incidents, meetings and material assistance which no man could have dreamed would have come his way.

Whatever you can do or dream you can, begin it. Boldness has genius, power and magic in it. Begin it now.”

That quote by William Hutchison Murray was a longtime favorite of mine for years. No more. Mostly because I learned people were viewing those words through a very different lens than mine. As a Christian, I never viewed the quote as meaning we – mere mortals – have the power to bend the universe to our will. Belief in God forbids any person from seeing these words as human power to attract whatever we want. The law of attraction and the “secret” are rubbish. Delusions of mankind thinking he’s his own god, able to do as he pleases. As though the path forward is through our self-centered hubris.

No wonder Dr. Peterson speaks so frequently against our malevolence.

ill will, hatred, spite; pleasure in the suffering or injury of others

The principles spoken of in the quote are powerful. More so when the context is our human capacity to influence our own lives, which is completely congruent with God’s divine Word.



Drawing back.










Unforeseen incidents.


Material assistance.








Now we’re getting somewhere. Maybe it’s our first time. Maybe not. But it’s progress if we’re internalizing the quest when we ask and answer the questions of “wouldn’t it be great if” followed by the pronoun I, followed still by an action verb or some outcome nobler than a selfish desire.

Wouldn’t it be great if I were a millionaire?


Wouldn’t it be great if I were so valuable my work was deemed worth a million dollars by others?

Wouldn’t it be great if we had a vacation home here?


Wouldn’t it be great if we were able to have a place here so others could enjoy this as much as we do? Maybe more?

Once in a while, I have a conversation with people about podcasting because I do so much of it. People clamor for an audience. Greater numbers. More subscribers. More listeners. More shares on social media. More acknowledgments on a job well done. They’re mostly disappointed when I tell them I’ve been doing this for more than 20 years and I have very little idea about such things. And I currently produce 3 podcasts regularly – two of which are business-oriented with the desired outcome being greater exposure to business services. More plainly, the quest is to get more clients. To differentiate ourselves from the pack who isn’t out there giving away information, ideas, insights, and sharing experiences.

But I certainly want to expand the reach of this and my other podcasts. Because I’m so important? Because what I have to say, or what I think carries more weight than anybody else? No. A thousand times, no!

Because I’m confident that a word fitly spoken at the right time might just resonate with somebody – maybe YOU.

Wouldn’t it be great if I could help you in a moment where you needed it most?

I live my life like the little boy combing the beach to save the washed ashore starfish,  trying to make a difference to just one. For me, that’s enough. And if that starfish happens to you, then it makes all the difference in the world.

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