Turning 'What Ifs' into 'Why Nots': Pursuing Dreams Later in Life

When you're young, you have both the courage and naivete to dream wildly. You dream about where you're going to live, who you're going to spend your life with, and how you're going to spend your time. So much time. It's as though the dreaming is its own chapter. Then you either pursue the dreams, or you don't. And if you don't, it's okay. You extend yourself some grace. You acknowledge both reality and pragmatism, and you work to find peace.

Throughout this period, you either allocated resources toward your dreams or you allocated them towards all the other things which sometimes made your dreams look silly or selfish. You got used to it. But you also know how humbling the entire process can be.

But what if something sparks your interest later in life, and it reignites the dreamer in you? Should you outright ignore it, or should you use what you've learned over the years to actually put resources toward those dreams and ride the wave of excitement?

The idea of this column becomes irrelevant if you choose the former. So let's enjoy some time considering the latter.

Before we get too far, I'm going to both slap down an idea and then tell you that I'm not slapping down that idea. This column isn't necessarily about your dream car or your dream house. Buying a car you've always wanted to own certainly is noteworthy, but I don't believe it requires the sort of healthy and significant resource and priority reallocation which I'm advocating for.

Have you ever walked into a small business and thought "I would want to own a place like this one day"? Or have you ever vacationed in a city and thought "I want to live here permanently"? If so, and that gut feeling grew into outright pangs of desire, let's explore how you can turn those dreams into reality.

It would be foolish to not start with the non-negotiables. However, the non-negotiables are often what we screw up. And when it comes to trying to make a later in life dream come true, we tend to make negotiable elements unnecessarily non-negotiable. We anchor to cliche expenses, irrelevant habits, and perceived obligations, which when combined make the possible feel impossible.

There's an easier way to see if a dream is fiscally possible. Find the delta. What's the monthly financial gap between your current life and the life you are aspiring to? This allows you to park the scary thoughts to the side, and instead make decisions based on real numbers.

Let's say you've always wanted to live in downtown Chicago, but to do so would mean a complete upheaval of your life. Start with the monthly housing cost difference. For example, let's say the cost of the proposed place is $3,000 more per month than what you are paying now. Assuming your core income won't change because of this location change, how can you shuffle the rest of your life to bridge this gap? Don't say it's impossible until you try. Some expenses will naturally go away, some you will have to force away, and in some instances you will have to account for new, ancillary expenses which come with making the dream a reality.

The difference between doing this at the beginning of your adult life and later in your adult life is that now you have experience, resources, and hopefully, some wisdom. What you're likely to have less of now is fearlessness, appetite for the unknown, and a willingness to step backward in regards to lifestyle and comfort. Of course when you flip the advantages and disadvantages around, you can see why trying to create these same dreams when you were in your 20s was both harder and easier at the same time.

Over time, you've justified your choices by pointing to the opportunity costs, and you've been correct in your assessment. However, I believe if you re-examine some of your current ongoing expenses and satisfaction with those expenses, you might discover there's opportunity in pursuing new dreams, and the cost to pursue those dreams aren't nearly as spicy as you've assumed them to be.

You really should pursue your later in life dreams more than you're wired to do. I know it's the math that scares you, but the craziest reality of all of this is the math doesn't necessarily make sense for the 20 somethings either.