One thing that helped me through the years, is a specific mindset I’ve always naturally had without being aware of it, until I took the time to dissect it and analyze it.

Since young, whenever I had a strong desire, I would actively start working towards it. I usually read books and information about my goal and take action based on that, adjusting and trying different things, while learning from the feedback.

Inevitably I faced a lot of failure, rejection, fruitless attempts. But here is what I’ve realized I was doing, looking back.

Every time I failed my goal, I always created an even more ambitious and seducing vision. At that time, I hadn’t researched much about goal setting and vision yet, so the primary reason for doing so was that I didn’t want to live with regret.

My logic was simple. If I’ve failed at securing that job, that partner, that car, that trip, or that opportunity, then I must work towards a better one which will trump the missed opportunity.

If I get to a better scenario, then it will make the missed one look small in comparison and I won’t even bother thinking about it.

But on the contrary if I adjust my goal downwards, I’ll always have to live with regret and that annoying thought: what if. What if I got that job? What if I got that partner? What if I moved to that country, etc.

Life as an adaptive game

While this for me was a subconscious habit, I have now learned it was a crucial one and unfortunately this is not the way most people usually operate. The good news is that it can be consciously reprogrammed.

In fact, what most of us do when facing failure is quite the opposite: we lower our standards. We take failure as a sign that the goal was not attainable or that we don’t have the right skills yet and we aim for something lower, more ‘realistic’.

But this only creates a downward spiral making failure a more likely outcome and programs our subconscious mind to accept it can fail and that failure will be even rewarded with easier tasks!

To use an analogy, this reminds me of when I took the GMAT test for my admission to MBA programs.

GMAT is an adaptive test, it means that it doesn’t count the absolute number of questions you get right or wrong, but rather it gauges your aptitude by giving you progressively harder (or easier) questions until it can zero in to your limit. Your limit is when you hit a 50% rate on a certain difficulty-tier of questions without moving upward anymore. That’s when test has you figured out.

A friend who had done very poorly at the test, recognized it and pressed the quit button without seeing the score, (so it wouldn’t’ appear on his record since he planned to re-take it), because, in his words: “the last questions were super easy. That means I had reached very low”.

Part of the reason why I managed to score a 94thpercentile on the GMAT was because I enjoyed this process so much. As challenging as it was, preparing for the test was fun for me because of this structure and the way I framed goals and challenge, among other things.

Why small goals are harder than big goals?

One concept if often reiterate is how life is counterintuitive.

And so is goal setting. You see, in many cases small goals become harder to achieve than big goals.

And that’s primarily because big goals (or rather big visions) are so appealing, so important, so seducing, so compelling, that they have the power to pull you through all the challenges, the efforts, the failure and frustration, as they shine so bright ahead.

Small goals on the other hand, tend to feel mundane and not life-altering, so it’s easier in a sense for your brain to cop out and reason that if you have to put in all that effort, then it’s better to stay where you are.

Big goals also give you the feeling that there’s a lot to gain and little to lose, since they’re so big that if you miss them you’ve missed something that’s far from your current reality anyway.

Small goals have a little to gain but a lot to lose, because you know they’re only a few steps away from your current reality.

You can think in these terms: imagine you set the goal of running 200km, or you set the realistic goal of running 40km. If you fail the 200km run and retire at one third of the race, that’s still 70km, almost twice as much as what you’d run by succeeding at the smaller goal.

But if you go for the smaller goal, your mind and body will adjust to that expectation, making you feel tired earlier or look at the watch around kilometer 35 with that feeling of exhaustion typical of when you’re about to reach the finishing line.

Big goals give you more time

The beauty of big goals is also that they aren’t dependent on the time.

Big goals can be delayed by months, years, or even a decade and still be worth it.

If you set the goal to have a best-selling book, would it matter if it happens in one, two, five or even ten years? No, it’s still worth it.

What about buying your dream house, would it matter if it takes one, two, five or six years longer if you can live there for the rest of your life? What about your dream partner?

You see, big goals keep you hooked for the long run. Because when something is so meaningful, so life-changing and all encompassing, then it doesn’t matter if it takes one, two, five or even ten more years.

But small goals such as getting a small raise at your current job don’t have that timeline. You don’t get it for one year or two and you get frustrated and maybe want to quit your job already. And even if you get it, it doesn’t make that much difference in your life.

How to raise your bar?

Once you set bigger goals, small goals become just stepping stones. You almost achieve them without even noticing it, and much more easily than if you had set them as goals!

Back to my original example, this is what I did every time I faced failure. At first, I was comprehensively upset and felt like giving up. Often I thought I would never get an opportunity as good.

But I refused to settle. And that’s the absolute key of this whole process.

Even if an opportunity seems the best possible thing out there and you’re sure you can’t get any better than that, remember that this is only so from your current limited perspective.

Trust that the world, and the universe, are much bigger and more abundant places than you can imagine and they can manufacture opportunities 100X the size of the one you’ve just missed or failed at.

With that trust, I usually would rejoice and thank my failure or missed opportunity for showing me what’s possible and allow me to raise my bar above it.

Always raise your bar above it, never below!

Imagine that what you’ve just seen and missed, is only there to show you that it’s too realistic for being a dream, so it’s time to dream bigger. You’re destined to get something bigger and better.

No regrets

This is a crucial mindset to have and the more I studied goal setting and how the mind operates, the more I realized that falling prey to the downward feedback mechanism is one of the most dangerous traps we all subconsciously fall into.

But now, even after so many years and more studies in the field, I still love the first version of my internal dialogue, a simple but profound question to ask yourself for whenever you miss your goal.

Would I want to go for something easier and regret that big goal all my life, or go for something even bigger and make this failure or missed chance laughable whenever I look back?


Also published on Medium.

Riccardo Caselli

Riccardo Caselli is a psychologist with MSc in Industrial Psychology and an MBA from NYU. He is a published author and has worked for 13 years in senior HR roles in large corporations, living in Europe, North America and Asia, training and coaching thousands of professionals. He has practiced meditation, and different styles of yoga and Qi Gong for over 15 years. His biggest passion is personal development and he has created Zen @ Wall Street to share his thoughts and inspire more people to live a balanced and fulfilling life.

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