What Does It Take to Emotionally Succeed as an Entrepreneur? Here’s What I’ve Learned, One Year After Quitting My Job and Taking the Leap of Faith

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Snowboarder in Tannheim, Austria. Source: http://commons.wikimedia.org/wiki/File:Snowboarder_in_flight_(Tannheim,_Austria).jpg

Snowboarder in Tannheim, Austria. Source: Wiki Commons

It’s been about one year since I took my leap of faith and entered the world of self employment and entrepreneurship, for the first time in my life. It really was a leap of faith, because everything was so uncertain back then — how would I chart out my course, and how would I survive without a steady source of income? I had prepared myself as best I could, but I had no idea what lay beyond the horizon.

One year later, I can truly say that taking the leap of faith was one of the best decisions that I’ve ever made in my life. Like many good things in life, it took time to nurture things and see them grow before I could really see the fruits of my labour. The first couple of months were quite tough, as I figuratively got punched in the stomach not long after taking the leap of faith, sending my remaining side income crashing to the floor. This was certainly the impetus I needed, as I soon started a new book project and doubled down on my entrepreneurial efforts.

Things got a little bit worse before they got better. I had some cash reserves to see me through thin spots, but I didn’t have a huge stash by any means, and past the middle of the year, I watched with increasing trepidation as my reserves headed toward $0. This was part of the risk that I took on and that I accepted, but it still hurts to see it happen. I worked steadily through this time, and in the second half of the year, I started to see the results pay off. By the beginning of the fall, I was climbing up the mountain, and I was able to surpass my old day job in terms of income.

Is it for everyone?

Since then, I have continued to see ups and downs, with large income swings and occasional burnout. I’ve also benefited from experiences I never would have had, had I not taken the leap of faith. It’s been an incredibly fulfilling journey, one that has been very rewarding and that I plan to continue, and one that I’m grateful to have had the privilege to undertake. I often get asked “what are the biggest challenges to entrepreneurship?”, and “is it for everyone?”

I definitely think it can be for everyone! I’ve already covered the financial aspects many times before, so in the rest of this post, I’ll focus on what it takes to survive emotionally and spiritually. Entrepreneurship can be tough, but no matter what happens, I believe that everyone is capable of it, and that the experiences can greatly enrich your life. Warning: this post gets personal! Don’t read on if you came here looking for stats or financials. :)

Build your success on past failures

This isn’t the first time that I’ve decided to undertake an entrepreneurial venture, though it is the first time I’ve taken a leap of faith and gone all-in. A couple of years back, I worked for several months with a fellow colleague on a project that we believed would be a great hit, and we even spent a lot of time analyzing the market and competition to cover our bases. We were actually fairly spot on with our analysis of the situation, but unfortunately, we just didn’t have the skills or experience to pull things off successfully.

I always had my share of regrets about failing, and I felt like I’d let my partner down. What if we had just worked a little harder? What if we had gone full-time? For a while, I felt like an abject failure as an entrepreneur, and I thought that I’d be better off just sticking to a day job.

In spite of the failure, I learned many valuable lessons, both about entrepreneurship and about myself. I was certainly better off for having taken the risk and having given things a shot, and I don’t regret having done that one bit.

Embrace each failure, figure out what went wrong and why, and learn what you can do better next time. You should never become results-oriented and regret having taken a shot, just because it didn’t work out one time. I eventually ended up taking a leap of faith, and one reason I have done a lot better is because of the lessons I learned during the time I took this previous shot. Look at how many times many of the greats have failed, whether in sports, business, or elsewhere. Success is as much about preparation, practice and perseverance as it is about luck and other factors.

I’ve missed over 9,000 shots in my career. I’ve lost almost 300 games. 26 times I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.

– Michael Jordan

Success doesn’t depend on your background

Some people think that to be an entrepreneur, you have to have a certain personality or a certain look. Maybe you need to be very extroverted or optimistic, or maybe you need to have a certain background. You might think that you don’t have what it takes because you don’t fit within that image, and I used to feel that way about myself, too. These days, I’m not sure that this stuff matters as much as some people think it does. I personally have neither the good background nor the highly extroverted personality that you’d typically associate with the image of an entrepreneur.

I didn’t have the right background growing up. I was born to a teenage mom, and my father abandoned us soon after. My mother regretted the pregnancy, and things were so unstable for a long time, switching schools in the middle of the grade and moving from place to place. Later on, she found another husband, started a new family, and I was slowly pushed out of their lives. These days, I always hear from 3rd parties about how great their daughter is doing, how big their last party was and what a great family they have, but that’s not the situation I was born in or grew up in. I often have nightmares where I am living with them again and things are well, but something always goes to hell and I can never figure out what went wrong.

I also don’t have the personality you’d typically associate with an entrepreneur. I sometimes get so anxious I feel like puking at the thought of meeting a stranger, and being born to a teenage mother who abused her body at the time which led to some complications, I’ve also always been a highly self-conscious person.

In spite of things, I was still able to graduate university, find work, find love, take a leap of faith and surpass my old day job income; I am certainly no billionaire nor even a millionaire at this point, but I really cannot complain, either! Don’t get me wrong — I’d much rather have had a “typical” childhood rather than the messed up situation I was born into, but it just goes to show you that things are less predetermined than many of us think. If you push hard enough, you’ll eventually break through, and achieving a measure of success is a very powerful motivator.

As Guy Kawasaki mentions in “The Art of the Start”, we can learn a lot from reading up on the lives of some of the great entrepreneurs of our time, including Bill Gates, Oprah Winfrey, Richard Branson, Sergey Brin, and Steve Jobs. Taking things at face value, would you have ever expected all of them to go as far as they did? Were they all “predestined” for it? Many of them have their own unique weaknesses and flaws, and many of them have gone through periods of self-doubt.

Just as a couple of examples, Richard Branson had quite a few problems in school as a dyslexic, Oprah Winfrey was a victim of sexual abuse, and Steve Jobs spent his last years battling with pancreatic cancer. I personally find this incredibly humbling, that these people that I look up to could have faced such adversity in their lives, and found a way to succeed in spite of it.

Never give up on yourself

In the end, I believe that what truly matters is how much good we can add to this world, and how we can improve the lives of others. If there’s something that defines us all as being human, I think it’s that no matter where we are in our lives, nobody really has it “perfect”, even if that’s how things seem on the outside. We can all benefit from being more empathetic and less judgmental toward others and ourselves and understanding our shared humanity, as I believe that is where we can find our strongest ability to overcome anything: our hope & faith in ourselves to succeed.

Never, ever, ever give up on yourself! You can give up on a project when it’s not working out and learn from your mistakes, but you’re still alive, so go out there and fight again another day! I do believe in Karma, in the sense that we can do good things and add to the total amount of goodness in the world. By taking the shots, failing some times, and reaching success in other times, I was able to find love and find my own success, and I can truly say that I am happier than I’ve ever been. I’d be lying if I said there weren’t days where something got me down, but I now have a flame of hope to help me forge on ahead.

Above all, you want to create something you are proud of. That’s always been my philosophy of business. I can honestly say that I have never gone into any business purely to make money. If that is the sole motive, then I believe you are better off doing nothing.

– Richard Branson

So long as we have the breath of life, we have the capability to improve this world for the better, and to me, this is what entrepreneurship is really about.

Dear reader, how do you define entrepreneurship? Is it like war, where it’s about cutthroat competition, a race to the bottom, and a fight to slice up the pie ever more finely? Or, is it more like love, where you can gain your greatest success by loving your customers, empathizing with them, and doing what it takes to improve their lives? 

It has taken me an incredibly long time to get over my own sense of shame for all of my failings, but in doing so, I have become a better lover and a better entrepreneur. Accepting failure has been a key to success, as well as maintaining undying hope and faith in the face of adversity. Will history judge where we came from, or where we ended up going?

Faith is taking the first step even when you can’t see the whole staircase.

Returning violence for violence multiplies violence, adding deeper darkness to a night already devoid of stars… Hate cannot drive out hate: only love can do that.

– Martin Luther King, Jr.

The real test of an entrepreneur is in the mind. Failure will wear you down, and behind every successful entrepreneur lies a long string of failures. These failures should be taken for what they are, with no regrets, for each gives invaluable experience toward future success. I did not give up, and in spite of previous failures, I have been able to surpass my day job in every single way, and I am happier than I’ve ever been. The biggest obstacles along the way were, in fact, my own fears and doubts. 

An entrepreneur doesn’t need a privileged background, nor does he or she need to have the stereotypical personality, as these factors are not really required for success. My customers don’t care about where I’m from or what wakes me up at night; what they care about is the value that I add to their lives. Some of the most admirable entrepreneurs have faced incredible challenges, but what matters is how they have changed the lives of millions for the better. So long as we never give up on ourselves, and always strive to make a difference, then we can never truly fail. 

Please let me know if you have any questions for me on any topic regarding my leap of faith, regarding finances, dealing with setbacks or negative feedback, or really, just let me know what you have on your mind, and I’d be glad to share my thoughts.

What Does It Take to Emotionally Succeed as an Entrepreneur? Here’s What I’ve Learned, One Year After Quitting My Job and Taking the Leap of Faith was included in the following carnivals:

Carnival of Financial Planning at Good Financial Cents
Carnival of MoneyPros at Drop That Debt
Carnival of Retirement at Making Sense of Cents
Finance Carn. for Young Adults at Femme Frugality
Y and T’s Weekend Ramblings at Young and Thrifty.ca
Yakezie Carnival at The Frugal Toad

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  1. says

    Sorry to hear that your entreprenership experience didn’t pan out as well as hoped. If its any consolation, a friend of my started two businesses. His first one failed and the company was insolvent. The second was sold to a division of an S&P 500 company.
    The learnings and experience from doing something once can be invaluable for a subsequent, more successful attempt

    • says

      The current time is doing much better. :) It did take me a while to get over the first time. Your friend’s experience seems common from a lot that I’ve heard, and it’s important to get back on that horse and try again!

  2. says

    I think you always need to try or you feel that you have lost without trying. Most if not all successful people have had failures, but they keep trying. When you reflect on your experience you will do things differently. I keep evolving with my blog because I have not quite found the right road yet.

    Just a suggestion, don’t dwell on all the negatives of how you grew up. I think you have accomplished a lot and you should be proud of what you have accomplished.

    • says

      I agree, I think it’s important to keep trying different things and evolve your direction, because each experience gives you knowledge that you can build upon to do things better the next time around. Some of these will seem like “mini failures” from one light, but each is also a learning opportunity, and by opening up risk taking a bit we can learn much faster.

      I used to find it really hard to not dwell on the negatives, but finding success does turn into a powerful antidote against that. Some people are naturally optimist, but too many are pessimist, especially the way I used to be once upon a time, and hopefully they can see that none of that stuff has to matter. I do believe that the walls that people perceive are more illusory than real, especially in today’s world, and if you want it you can definitely go for it!

  3. says

    I feel your pain I run a manufacturing business and I completely know what it’s like to be up one month and down the next. On top of that I face some really tough competition and very high overhead with some months over the $100K mark.

    I believe a businesses success breaks down to 2 things. Doing the right things long enough. Really that’s what a business is doing, a specific group of actions that when done for a long enough time will create a successful business.

    I’m sorry to hear your business hasn’t done so well, just take the time to learn from your mistakes and move on.

    • says

      Hi Chris,

      100K is quite a bit of overhead! There is a lot of competition in my sector, but one advantage is that overhead can be low since it mostly deals with bits and bytes rather than physical items. Also, I didn’t mean to confuse you or anyone else — I am doing quite well now! :) Let me know where the post might not be clear, we had to restore from a backup and I might need to fix things up a bit.

  4. Helen says

    I have read many inspiring post from you but, by far, this is my favorite. Probably because I had similar experiences and beliefs in life – like believing in Karma and adding to total amount of goodness in the world [wtihout sounding righteous or anything I hope].

    I hope this post will reach those that are in need of a emotional/intellectual/spiritual boost (come to think of it, don’t we all? hehe…)

    Thank you.

  5. says

    I agree with you. In every entrepreneurial pursuits we make there are always that risk of failure. It is very important to never give up on your dreams and yourself. Although, l think that every entrepreneurs should have an exit plan so as not to over-extend our finances when the. going gets really rough and tough.

    • says

      I definitely agree with the need for the exit plan. I think you can divide things into a “core” that shouldn’t be touched, and an “extension” that is safe to risk on an entrepreneurial venture of some sort. The core can include a base level of savings, as well as skills you know will be able to get you a job, should you need one. Even if you don’t make a penny, you can always fall back on the core.

  6. says

    Kevin, well done for going “all-in” and taking the plunge full-time. I see you had some reserves which is essential I think if you are doing this as many people seem to forget that it could be a while before you start to earn enough to even pay the bills so that could finish their dream off and discourage them before they got to the good bit!

    I have been an entrepreneur for 20 years and after a few bad decisions, have had to go back to part-time work whilst I get going on my current businesses – which I am totally committed to and can see will totally reach my financial goals given time. Working for someone else after all these years is very strange but I can see how people get sucked into the so-called security. Although really there is nothing secure about a job these days is there?

    Enjoyed your post and more power to your elbow for the future. May we all be truly successful in our various projects.

    • says

      I definitely believe a reserve is essential! I have a few other posts that go more into the financials, and it took a good six months before I started to see enough revenue that I could start replenishing the reserve. Even a job is not too secure these days, I agree — I like the feeling of being able to make the decisions, even if the future is even more uncertain.

    • says

      Thanks, I appreciate that! :)

      P.S. I wanted to leave this comment for you: “Good thoughts and tips to follow, Jan! There is a part of our minds that holds us back from the risk, perhaps because in the past we might have gotten eaten by a tiger or something. These days, the consequences are usually far less drastic, and a shot can be worth it.”

      I didn’t see a “guest login” feature and didn’t want to use another account; that might be something worth adding.


  1. […] What Does It Take to Emotionally Succeed as an Entrepreneur? – There’s a lot of us who would love to strike out on our own and become entrepreneurs, but are too fearful to do so.  (Unless we find ourselves unable to do anything else, of course.)  Kevin of Invest It Wisely shares some of his stories from doing just that, and making more from entrepreneurship than his previous job (congrats, by the way). […]