What if You Prepare for the Upside? 

A favorite comment an advisor once made to me: “Let’s hope everything goes better than you’re projecting… you know, things often do.” 

My whole goal in life is to plan and prepare as proactively, intentionally, and strategically as possible. My life’s work and my business’s Mission have mostly been about helping others do the same. 

But so much of our planning, strategizing, and preparing is done to avoid or guard against the downside. We buy insurance so we’re covered in a “loss”. We save a little extra in case we “lose money” or “don’t make as much”. We make plans for how we’ll handle things that “don’t work out as we expect”, or if someone goes on attack “against us”. 

All of this is critically important, both personally and professionally. But all of this has a negative bent. 

What if … everything goes well? What if it turns out to be better than expected? What if you achieve your goals faster than you planned? 

I ask these questions quite often. Why? Because often, good people doing hard work well will achieve far more than they anticipate on a much faster timeline. And so, so many of us are unprepared to handle unexpected fast success. 

Imagine you’re working in a successful senior-level sales role. For the last two years, you’ve earned your very nice base plus a $20,000 year-end bonus. This year is on track to be even better than the last two, and you’re already thinking about how you’re going to use that $20,000 bonus. But then you find out your bonus is $30,000! Congratulations! 

If you’re like most people, you don’t have a plan for an extra, unexpected $10,000… and you’re very likely to fritter it away on stupid stuff! 

Two minutes of planning, but in Stoic fashion not getting attached to the outcome, would allow you to say, “If my bonus is higher this year, I will save 20%, invest 20%, and spend the rest on either of A or B.” Now, the upside doesn’t surprise you, the benefits are not frivolously wasted, and you put your good results to good use with a little fun! 

What if you reach your five-year goal in only three? What if you get an unexpected extra bonus or a sudden windfall? What if your portfolio grows faster than anticipated and you can stop working sooner? 

If you don’t have a plan for what to do in the best-case outcome, you’re likely to make suboptimal choices. Take a few minutes today and ask yourself, “What if?”  

 

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