Go Start Something and Have No Regret!


I have never been very much fond of people writing about the continuous transcendental analysis of our human existence and spirituality. My needs to revisit my doubts and urges regarding the meaning of life, the universe and everything else where pretty much solved the day I found out the answer to all of them was 42.

I guess this apparent lack of depth or spiritual curiosity has a lot of different philosophical and psychological explanations and is probably the leading cause of why I decided to quit pursuing my childhood dream of becoming a songwriter when I was 17 to study International Business. However, not long ago a good friend of mine posted on Facebook a link to blog post analyzing a book that compiled the 5 most common regrets of people in their death bed, and suddenly something clicked in my mind.

The book that triggered this post (Amazon)

Now, hold your horses! Don’t worry, this is neither a cheesy life-changing realization piece nor is a metaphysical analysis about life and death. As dark as it might seem, while reading the post I suddenly realized how well these regrets summed up all the right reasons and the right mindset to consider getting into the entrepreneurial life.

As many have covered before this post, founding a startup has often very little to do with a rational decision and more with an urge. Being an entrepreneur is more a lifestyle than a career.

F. Trías de Bes (Trabalibros)

In 2007, Mr. Fernando Trías de Bes did a terrific job covering on “The Little Black Book of Entrepreneurship” all the reasons why people shouldn’t become entrepreneurs. Most of the reasons mentioned in this book accurately covered the dreadful perks and situations you will suffer as a startup founder that you wouldn’t have to suffer in the corporate world. However, few of them did focus on the real underlying factors common to all human beings that really matter in the end: The sentiment of personal failure in our pursuit of happiness and the unforgiving regret of the irreversible personal choices we make throughout our lives.

This is where these 5 most common regrets of the dying come into play. As I said before, being an entrepreneur is in most cases not a career choice but a lifestyle. Throughout the following analysis, my intention is not to trivialize the subject of death and regret but to leverage on these 5 sentences to help future wannabe entrepreneurs avoid the most painful personal frustrations by making an honest analysis of themselves and achieving the right mindset and motivations to start this journey.

Without further ado, let me introduce you to my personal take on how the 5 most common life regrets can prepare you for your entrepreneurial journey.



#1 “I wish I’d had the courage to live a life true to myself, not the life others expected of me”

One might think that by starting an entrepreneurial venture, you are already refusing to live the life others expected of you. However, this doesn’t necessarily mean you are living a life true to yourself. Are you starting the entrepreneurial venture you truly want to start? Or, in other words, are you solving a problem you really want to solve?

Most non-entrepreneurial people will probably assume entrepreneurs have a high tolerance for uncertainty, risk, and most of all, failure. It seems impossible for them to acknowledge the probability of other people having a different concept of failure. But, the true entrepreneur, the one that is in it for the long haul come what may, is someone whose only definition of failure is remaining inactive and not trying to solve the problem(s) they want to solve.

That is why the correct way to approach an entrepreneurial venture is to (1) figure out the world’s day-to-day problems that really get you all worked up, then (2) pick the ones that you are capable of solving and (3) narrow them down towards the ones that are big enough and painful enough for other people, that you might have a chance of making a living out of solving them. This is the correct flow for the procedure and it never works the other way around.

After all, keep in mind you are bound to spend at least 3 years of your life leaving on sub-par economical conditions compared to your equivalent corporate deskjob, so you better be passionate about it!

#2 “I wish I didn’t work so hard”

Now, this is a tricky one. Regardless how many times you can recite entire passages of wonderful books like “Rework”, “Maverick”, “The 4 hour work week” or “Delivering Happiness”, most likely your work-schedule has higher probability to resemble more Steve Jobs’ (hopefully with just a fraction of his success) than of Tim Ferriss’. However, regardless on the disparities between Steve Jobs life and the 4 books mentioned above, if you have seen Mr. Jobs’ famous 2005 commencement speech at Standford University, there is one thing that really tackles this potential regret: It shouldn’t feel like “working”.

Ask yourself if you are truly tackling a problem that really matters to you and a fair share of people in the world and there is a possibility of making a living out of it. Analyze if you have completely fallen in love with the idea of solving this problem for the rest of the world to the point of leaving behind a much more “secure” life in the corporate world because just can’t live with the regret of not having at least tried. If the answer to both is “yes”, then it doesn’t matter how much you manage to follow or not the doctrines of Ferriss, Hsieh, Semler or Fried: It is completely impossible that you end up feeling you have worked too hard, because you were just doing what you loved most.

#3 “I wish I’d had the courage to express my feelings”

Entrepreneurship is a tough and quite lonesome journey. A famous investor in Spain says that he normally likes to stare at the faces of the entrepreneurs he interviews to see how much they resemble to “a Berber capable of surviving a life of several years traveling through the desert”.

The temptations to quit and the frustrations that you are going to face are numerous, and it requires a very emotionally strong person to be able to put up with it. Hence, you will have to learn to say no to a lot of people, a lot of times, with complete utter sincerity and without any regret in order to avoid losing the course to meet your goal.

In other words, be humble, ask for help, share your joys as much as your sorrows, don’t bottle things up, speak up what’s in your heart from the top of your lungs and do what’s right for the project to get where it needs to go.

#4 “I wish I had stayed in touch with my friends”

As covered in the second point, building a startup is a lot of work and, in most cases, it might seem to give you almost no work-life balance to the naked eye. Of course, if you manage to build a project that almost always doesn’t feel like working, what the “Average Joe” might think of your lifestyle will not be something that concerns you.

However, it is important that you manage to step back, take breath, smell the roses, reboot your brain and/or find comfort and peace of mind. Sometimes, when you have manage to find the right project for you the line that divides “focus” and “obsession” might become blurry. Unfortunately, what might seem just a dysfunction on your personal life has a huge risk of becoming a huge potential threat to your professional life, relations and the project at large.

Although is inevitable that your social life might not be as active as before. Find the time to get away from yourself, vent your worries and enjoy the company of the people that you love the most. The people that will pick you up when you are down, the people that will tell you if you are wrong even if you don’t want to hear it, the people that somehow always manage to make you laugh; those are the ones you need around you.

After all, as I said in the third point, the entrepreneurial life is quite a lonesome journey. Find the time to fight that loneliness and avoid jumping from “focused” to “obsessed” or else prepare for a hard downfall.

#5 “I wish that I had let myself be happier”

Life is too short to be miserable and the entrepreneurial life is not made for the faint of heart. So don’t embark in a journey that doesn’t have your own personal happiness and sense of fulfillment as the ultimate goal.

Choose something that feels greater than yourself, that drives you, that gives you a purpose to wake up every day and smile. All in all, choose something that no matter what happens, come what may, whatever the final outcome is, makes every second of your life, a second worth living.



An entrepreneur capable of fulfilling successfully all these realizations and integrating them into their mindset is an entrepreneur that would eventually never lack a customer, an investor, a co-founder, and most importantly, a bright future awaiting for him or her at the end of the line. Nobody is perfect and of course there are no secret recipes to achieve it. Being happy is a lot of work, but it is a work worth doing.

The entrepreneurial life is all about resilience. Go start something you love and have no regret!

3 thoughts on “Go Start Something and Have No Regret!

  1. Agree! superb post. You’re a natural! maybe you didn’t end up song-writing… but just writing like you do is certainly not a bad second best!! :o)

    Just thinking: aren’t we picturing a kind of *Superman* for an entrepreneur? anyone who is not resilient like a bamboo, or so utterly passionate as to give up all relationships and even their own lives to do whatever it takes to follow it, or emotionally as strong as Nadal to never give up, to always-do-what-you-have-to-do-when-you-must-no-matter-what… wouldn’t this make them step back?

    Maybe we are picturing the PERFECT entrepreneur -thus someone who MUST be successfull- but many, though not perfect tens, would love to try and see for themselves what it takes. Many not perfect tens may not “feel” their entrepreneur ADN until they get to it.

    I certainly would never encourage it out of need or out of somebody else’s expectations (i.e. family business), but, if aware of what it will take, willing, and crazy enough to give it a try, I would certainly not discourage it… but just help them a little bit more! ;o)

    • Thanks! I agree with what you say too.

      The objective of this post was not to discourage but to help future entrepreneurs to aim high not only in their professional development but also in their personal development. I believe if you don’t take enough care of your personal psyche and morale, the entrepreneurial path can be unnecessarily mind-drilling.

      My intention actually was to encourage them, guiding towards what I believe is the right mindset to start. If you prioritize a cause you really believe in, that feeds in your personal happiness and those around you; just by that positive reinforcement you surprisingly can become twice as resilient without almost no effort.

      Sorry if the post can mislead people to discouragement. It was never my intention.

      • Just trying to rise the debate 🙂

        I personally didn’t find it discouraging and, trying to make my way in the *entrepreneurworld* myself, I must say it is exactly as you pictured it. That is: empowering and mind blowing. But tough – much more than one can imagine.

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