The Most Important Question You’ll Ever Have to Ask Yourself

It’s a question all of us have to face. It often comes right after we successfully accomplish a major goal, or when we’ve achieved some degree of success. In fact, that’s when it hits us the hardest, after riding that wave of victory, feeling good about ourselves, celebrating our accomplishments. 





Episode 45 - The Most Important Question You’ll Ever Have to Ask Yourself

by Roger Reid


It’s a question all of us have to face. It often comes right after we successfully accomplish a major goal, or when we’ve achieved some degree of success. In fact, that’s when it hits us the hardest, after riding that wave of victory, feeling good about ourselves, celebrating our accomplishments.  And why not?. We deserve it. We’ve worked hard. We put in the time, we did whatever it took to overcome the obstacles and challenges. And now, we can sit back and enjoy the reward. That might last a few days, a few weeks, maybe as long as a month.

But then, we have to face the question…. Now what?  What comes next? Do we go back to work and pursue the next goal on our list?  Or do we change directions and go after something entirely different?

Hey, Welcome back. This is Roger Reid with another episode of Success Point 360              

When we look at the traditional advice having to do with achieving success –what we might call the supposed enlightened path to attain all the things we want out of life, it usually takes the form of five or seven or ten steps that include the predictable recommendations of identifying what you want, and then formulating a plan to get it. That typically means setting a goal, making it time-bound and measurable, and then breaking it down into action steps that we can take on a daily basis. Eventually, if we’re persistent and willing to make the necessary sacrifices, we arrive at the end game – and we acquire what we want, we achieve a higher level of success, or we create more notoriety and recognition for ourselves.

A lot of people use this model –because it works. Most of the time, anyway. Especially for those who are just starting out, who don’t have a lot of life experience, or aren’t sure what it takes to accomplish an important life goal.

But what about those who have been in the game for twenty years?

It doesn’t matter if your self-employed or you’ve found a place to excel within the corporation, we all face a time in our life when we have to ask ourselves, Now what?

And how we answer that question can make the difference between living a full and satisfying life and one that leaves us full of regret.

And that may not seem like an overwhelming problem, because the obvious answer is to have a long list of new objectives to concentrate on. But there’s more to it than that.

What if those new opportunities don’t seem as exciting as they used to be, and the new possibilities seem obscure and convoluted? What if looking at the next goal on your list makes you wonder why you put it on the list in the first place? It might have seemed fine at the time, but now? It doesn’t excite you, it isn’t compelling.

So what do you do?

Part of the problem is that we’ve been using the same techniques for achieving success for most of our lives. And it’s a strategy usually comprised of some combination of goal setting, time management, career and life planning to identify what we want and to focus our time and effort toward attaining it.

And on the surface, there’s nothing wrong with that. But over time, there’s a part of us that begins to realize that following the same plan – over and over again – is going to always bring us back to the beginning, to start over with a new objective,  a new goal.

And that’s when we realize it’s more than just the goal we’re after. The new car, the new house, the increase in income – yes, those are great, and they can certainly make our lives more comfortable – but even after we acquire those things, what if there’s something missing, because you were looking for, hoping for,  something more satisfying in the long term. The car will wear out, the new house will become a financial liability. And that increase in income? In most cases, our spending patterns rise in an equal amount, so the level of financial security remains about the same.

Here’s the point. And it comes in the form of a question . . .

What do you do when the tools and techniques you’ve relied on to build your life to this point no longer create that level of satisfaction and happiness you’d hoped to find? What happens when the accomplishment, the acquisition, the achievement of what you thought you wanted, no longer satisfies you?

And when you extrapolate the process into the future – it’s easy to see the constant and never-ending cycle of wanting more, getting more, then raising the bar, hoping the next level of success will be the one that finally gives you that sense of accomplishing something significant, something that changes your life.

The irony is that we already know this. We learned it as kids: The electric train set we just had to have at age ten gets replaced by a new bike at age eleven. Then at sixteen, we have to have a car. And at twenty, we’re sure that having our own place will change our life.

There’s an old adage that tells us that, getting what you want isn’t always the best thing.  Because that’s when we start counting the cost. And it can force us to ask the hard questions:

Questions like, “I gave up my kid’s ball games for this?  Now, my son barely speaks to me.” Or the real heartbreaker, “I let my wife leave me because I thought a vice-presidency was more important than being a good husband?

And yet, we still push ourselves. We work hard for the prize. We tell ourselves this particular goal or objective will be the thing that finally changes our life for the better, and once we get it, then we can relax, then we can concentrate on things like family, our health, and how we feel about ourselves in a spiritual sense.

But that’s not usually the way it works, is it?

Life’s victories are short-lived. That doesn’t mean they’re not important, it means we need to appreciate them in perspective to the other important aspects in our lives.

Remember Buzz Aldrin?  He had the dream of going to the moon. He dedicated his entire life to it. And even as impossible as that goal was fifty years ago, he did it. He achieved his greatest desire.

And when he came home? Well, you can read the story or listen to it on one of the earlier episodes of this podcast. But in short, after the attention and celebration of his achievement had died down, he realized he wasn’t happy. He’d accomplished what he’d set out to do, and that question, “Now what?” began to influence his every waking thought.

As a result, Aldrin experienced severe bouts of depression. He turned to alcohol, and eventually, his wife left him.

That’s how powerful the question, “Now what,” really is. And even more important, is how you answer it.

And I know some of you may be thinking, Hey, if Buss Aldrin couldn’t get it right, what possible chance do I have? Am we all doomed to experience disappointment and depression, even after we accomplish our most cherished and important goals?

Here’s what I’ve learned from taking a hard look at the success of those who’ve pushed themselves to do the near-impossible, to take on very challenging goals, and eventually achieve what they set out to do.

You never arrive. Never.

You finish one race, and then it’s time to start the next one. You may have time to rest, you may not. But you can’t stop. You can’t say, “I’ve made it,” and then sit back and expect the rest of the world to placate you with adoration and hero worship. Because it doesn’t last. There’s always another competitor, another person who has even greater dreams, more challenging goals, and when they push themselves far enough to grab the gold ring, you become another tiny blip on the screen of history.

So how do we answer the question, “Now what?” in a way that makes sense?

In fact, Is there an answer? At least, one that makes sense?

Wayne Dyer often said that we needed to start arriving and stop striving – his way of telling us to live in the moment, to appreciate the people, places, and things that make up our life in the here and now.

But I know that doesn’t work for everyone. There are too many of us who need a plan for the future. We need new opportunities to push us forward, we need new objectives to keep us motivated and excited about life.

It’s what gives us that sense of possibility, of making a difference. And as we make headway, we establish benchmarks, a time to look back and realize we’re better, more experienced, more capable than we were when we started our quest for a better life.

This creates what may seem like a huge conflict – a contradiction– in that while we need new goals to make our life meaningful, we inherently know that the process and the attainment of those goals don’t come with a permanent sense of satisfaction. It’s like riding a train that has no ultimate destination. The process is never-ending, and achieving one goal simply brings us to the next one, and then the next one, and so on.

And so, that makes the question, “what’s next”, not only important but critical.

So how do we approach it? How do we identify and prioritize the next step on the ladder, the next objective–especially after we’ve already accomplished a major goal that had previously occupied our attention, resources, and time for a significant part of our life?

First, we know that all the advice to be found in the self-help books has limited value – especially for us. We’re not neophytes. We’ve been through the process. We’ve recognized our talents, abilities, and weaknesses, and we’ve developed the flexibility to try different approaches to arriving at our desired level of success. So all those books, and articles, and podcasts dedicated to identifying your passion, reducing it to tangible goals, and setting a plan to accomplish it, is the equivalent of trying to solve a graduate-level engineering problem with a third-grade curriculum.

We need a different approach – a different way to choose what comes next in our life, keeping in mind how that will ultimately affect our future.

The first place to look for new life priorities is the options that we had to set aside, the ones we had to put on hold,  to accomplish our highest priority goal. These are the things we had to sacrifice, because at the time, we readily accepted the idea that we couldn’t do it all, we couldn’t be everywhere, for everyone. So we told ourselves we’d pay attention to those things later, after we’d accomplished that one thing that we had to do, that one thing that wouldn’t leave us alone until we’d finally achieved it.

So, identity those things that you had to ignore, the ones that had to be put on hold, and determine if one or more of them are deserving of being moved up in importance.

And I know that’s can be very subjective, as well as downright ambiguous and vague. So, let’s gets specific.

What about the spiritual aspect of your life? I mention that because it’s typically the first thing that’s moved to the discretionary side of the ledger – it’s the thing we most likely put on hold while dedicating our time and resources to a goal we thought to be more important.

And then there’s our health.  We often make our climb to success without any regard to taking care of our bodies. We eat garbage, we drink too much, and we forgo exercise because we don’t have the time.  And now, those years of abuse are catching up, becoming obvious. Regardless of how old you are, it’s time to do something about it, especially if you want to be in the best condition possible to take on life’s next challenge.

And finally, there’s our relationship with others. Our spouse or partner. Has he or she been neglected out of necessity –because of all those times you had to stay late at the office, or the dozens of business trips you took without her? And what about all those evenings spent at home, when you could have been enjoying each other’s company, but instead, you spent hours on the phone with business colleagues and customers. Sure, your spouse has been the brave little soldier. She understood you were working to achieve success for both of you. But now that you’ve accomplished some measure of that success, why not include her in the process of enjoying the reward by giving her the time you couldn’t give her in the past.

And what about the kids? How many ball games did you miss?  How many times did your youngest ask you to help her with her homework and you told her you were too busy with work? And what about that time when your eldest son asked you for advice on choosing a major for college, or how to handle an argument he’d had with his girlfriend? And you put him off, telling him you’d be available later because you were too involved to take the time to spend that fifteen or twenty minutes he was asking for.

Frankly—and I want to be honest about this—it might be too late. But that’s even more reason to try to restore the relationships with those that mean the most to you.

I know that’s only three options to consider. But for most, especially as we get older, we often realize they are the most important aspects of living a life that is ultimately satisfying. Yes, the money, the prestige, and the recognition are compelling, and when we finally achieve an important objective, it’s exciting. But just like all the other bright, shiny things in life, it can divert us away from the things that are ultimately more important, but we often take for granted.

So give yourself another chance to review the basics of life, to make a new set of choices, and this time, you can make those decisions from the perspective of someone who’s traveled a fair distance down the road. You know the cost of taking each and every step. So regardless of your age, make sure you get the maximum return from the time you have left . . . because there are too many people who leave this life with plenty of money in the bank, and a mind full of regret –because they realize, too late, that their hefty bank balance came with a price that was far more than they should have paid.

Hey, that’s it for this episode. If you have a question or comment, you can leave me a voicemail on the website, Just click on the voicemail tab located in the main header. You can also send me an email to:

Thanks for listening, and I’ll see you next time.

© 2021, Roger A. Reid, All Rights Reserved

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Be sure and check out my new book now available on Amazon in eBook. It’s titled Better Mondays: The New Rules for Creating Financial Success and Personal Freedom (While Working For the Man)

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