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Playing the Waiting Game? The Odds Are Stacked Against You

Updated: Jul 18, 2022

I want to take an unconventional approach in this post by examining why some folks wait so long to enjoy what they want most out of life. I think exploring your life’s passions or improving the quality of your life doesn’t require waiting for a specific time in the future. But some of us, particularly Gen Xers, have been programmed to set a big life goal, then put it on the shelf until retirement. To me, this is like putting your life on layaway.

The layaway approach to life is problematic for a couple of reasons:

1. Waiting for your perfect moment in the future takes you out of the present moment and traps you in an imagined future state with zero guarantees or certainties.

2. Give up your ability to attain the freedoms available to you now.

3. You set yourself up for disappointment when the future moment you’re waiting for never arrives.

Why do we play the waiting game?

The simple answer is that we’ve been conditioned to wait. From an early age, we are taught how to delay gratification. Some studies have shown that waiting can heighten your enjoyment experience, while others have found that delaying gratification for too long is problematic. The problem arises when waiting disrupts the balance between enjoying your present and expectations for the future.

There’s no doubt that waiting is a big part of the human experience. We wait for nine months in the womb to enter the world. Then, we wait to start school. Afterward, we wait several more years to finish our schooling. After graduating high school, we wait to land that first job and a promotion. We also wait for social acceptance when we look for those coveted hearts and thumbs up on social media.

The waiting game starts over again once you get to a place in life where you’re ready to start a family. You wait to find the right home, neighborhood, and school for your children. Then at some point, you wait for the kids to leave home. Waiting is a constant in life that, in some cases, we can’t avoid, like in our work and careers.

At work, you wait for the weekend because society has normalized overworking. Each week, you work yourself beyond exhaustion to get one step closer to paying off your life’s layaway plan. But have you stopped to do the math? The math doesn’t work, folks. All this waiting results in lost time, and you could use that time to take advantage of present opportunities to enjoy the things you want out of life. That’s why I’m spreading the idea of not waiting until retirement to begin living your ideal lifestyle.

My lifestyle transition taught me that the present is the best time to enjoy the things you want in life. I remember feeling drained and demotivated by the thought of putting off what I wanted in life until retirement. Once I made the shift, I saw my future differently and could better visualize what I wanted personally and professionally.

So, why are you waiting to enjoy the things in life that make you feel more whole, like traveling or making a lifestyle change? Playing the waiting game is a significant gamble because you place your betting that the future will arrive just the way you’ve planned. But I’ve seen plenty of examples where the future shows up with alternative plans. I’ve watched many professionals miss out on the opportunity to retire due to death, injury, or sickness. This circumstance begs a big question: How did waiting until retirement to enjoy all life has to offer become a thing?

The social expectations of waiting

As with other generations, Gen Xers received messages early in life about waiting until retirement to enjoy the fruits of our labor. These messages were ingrained in our consciousness over time. I remember learning about financial literacy skills as far back as elementary school. As I grew older, I listened to politicians argue over entitlement programs like social security and began to worry about what those debates meant for my financial future.

Flash forward several years, and it’s time to decide how much to contribute to your 401k plan and how much your employer will match. And let’s not forget all the messages from the financial services industry telling us that Gen X is woefully unprepared to retire because we haven’t saved enough money. These messages get coded into our psyche as keywords like long-term savings, money management, and preparing a nest egg for our golden years.

Over time, the messages constantly repeat in our heads, becoming the soundtrack for our decisions about enjoying life. But when it comes to Gen X, we’ve been conditioned to believe that retirement is a required developmental stage that we must wait for to enjoy life fully. And to me, that message is not just a myth. It’s a flat-out lie!

Why do I believe this? Because so many people don’t make it to retirement due to life’s unpredictable nature. One thing that breaks my heart is hearing stories about busy professionals on the cusp of retirement who die just as they're about to transition to the lifestyle they waited so long to live. And that’s why I’m committed to spreading that message of not waiting until your golden years to begin a new way of living.

The right time rarely comes along

We all play the waiting game on some level, and that’s okay. Some things take time, whether it’s waiting for the promotion, waiting to close on a new house, or even finding the right partner. I’m focusing on those events that we spend years waiting to enjoy, like exploring the world, becoming an entrepreneur, or moving to a new city. So, how do you break out of the pattern of waiting?

Here’s a simple thought exercise I use to decide whether to indulge my desires now or wait for a future moment. Ask yourself:

Are you gambling your present moment for an uncertain future?

If the answer is “Yes,” see if you can find your underlying reason to wait. Be brutally honest. If fear is the reason–whether it’s fear of failure, fear of missing out, or just fear of the unknown–explore how your fears keep you stuck. The reality is that something will happen eventually, no matter how long you wait. But that something may not be what you’re expecting. I realized this after waiting years to move to a new city.

Moving from Atlanta to Chicago was one of my biggest moves. The reason I made that decision was purely economic. I was working in the education industry, which Baby Boomers dominated. Many of them held senior leadership positions at that time, and I realized that those leaders weren’t retiring anytime soon. That’s when I decided to leave Georgia and increase my income.

Once I settled in Chicago, I realized that I should have explored new opportunities much earlier. I was in my mid-30s, and for the first time in my life, I was living outside of the south. I didn’t fully understand how limited my worldview was due to living in the same geographic region for most of my adult life. In retrospect, my decision to relocate came at the right time, but I still wished I’d moved sooner.

I now understand that I was fooled by an internal narrative designed to keep me safe. That narrative kept me in a holding pattern, living in the south. And I don’t think I’m an isolated case. I’m sure there are other Gen Xers with similar experiences. So, how do you shift your mindset from the false sense of security that waiting for the right time offers?

Shift your mindset to enjoy a more fulfilled life

When it comes to playing the waiting game in life, I’ve learned it’s critical to identify the specific thoughts and feelings causing you to wait for the right time. Maybe you feel like the benefits of waiting for the perfect moment outweigh the risks of deciding to enjoy the things you want in life sooner rather than later. Or maybe fear leaves you so much anxiety that you’re confused about how to make your decision and don’t know where to start.

Whatever the case, listen closely to the stories you tell yourself and see if you can connect the thoughts you’re having to the outcomes you’re achieving. If you understand how thinking impacts your results, you’ll get one step closer to making the desired changes. If you’re unsure about how to do this, don’t worry. I have several resources that teach you how to work through the process. Head to my website at and check out my blog post, What’s the Secret Ingredient for Making a Lifestyle Transition?

What’s next?

Again, I want to stress that there’s nothing wrong with waiting for the good stuff you want in life. But when you’re constantly waiting for the right moment, chances are you’re not focused on how to use the present to your advantage.

Remember to ask yourself my level-setting question: Are you gambling your present moment for an uncertain future? Explore the answer to my question and see if that helps you gain more clarity about your potential to enjoy the freedoms you crave in life now instead of waiting until retirement.

Let’s keep in touch on social media!

Want to connect on social media? Follow me on Facebook and Instagram

Need support with your lifestyle transition? Join the conversations in the Gen X-Unlatched Facebook group

Want to create a clear path to your lifestyle transition? Go to my website to reserve a complimentary strategy session


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Dr. Mario Jackson 
Lifestyle Transition Coach & Speaker

Office Hours with Dr. Mario 


Empowering Gen Xers to ditch the idea of waiting for retirement to enjoy the lifestyle they crave in life NOW!

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