Keep Calm and Keep on Truckin’

keep on truckin2If you believe everything that you read you would think that being an entrepreneur is all if not mostly one high after another; every idea being funded, every app getting built and every team jumping for joy every day. The reality is quite the opposite. But we do it because of the intense satisfaction we get from doing something meaningful. Something that we are passionate about.

Recently, I received an email from a friend and fellow entrepreneur and I thought I’d share with you what is to me a rare glimpse into just how hard the hard work of building a business can be.

Their comments to me are in gray and my responses are in blue.

Not sure if you are able to understand how I feel.

I am going between excitement and depression.

– Completely normal. As I like to say, having your own startup is like believing in God, your faith is always being tested.

Excitement, because I envision the outcome, because I think about all the good indications, that are telling me we will have a big success.

– Yes the early years are in some ways the most exciting as you’re fighting the early battles. As it gets older you’re fighting more traditional business battles of selling and making a profit.

Yes! And at the beginning you have a vision but later it is more about implementing things, which often means dealing with admin stuff, testing products, and seeking more funding.

Depression, because I think about the time I already spend on the project. I had always thought this would be a 4 months development task but I’ve been at it over 2 years now.

– It always takes much longer than you think. Like deciding to fix something in your house. You think you can do it in a few hours and three days later you’re still working on it. Having a startup is no different.


And then I participate in these mentoring sessions, with mentors that I feel are much less experienced than me, and with co-entrepreneurs that are much younger. So I often feel misplaced.

– I just listen, some young guys have no idea of what they are doing and yet one of the best most mature entrepreneurs I know is less than 30 years old. He’s just amazing. So, you never know. I just keep an open mind and see what people have to say. There’s always some wisdom you can pick up.


And then there is the lonesomeness, as I seem to be the only one who really cares. This is only increased by having to travel to many different places for the project.

– This is perhaps the greatest challenge. Your focus is 100% on the business and then you realize that you’ve neglected your personal life.. So yeah, entrepreneurialism is difficult for a personal/family life but that doesn’t mean it’s not impossible, it’s just a major hurdle.


– I think the best way to fight loneliness is to do things and be involved in something that is completely unrelated… a hobby or a sport or an activity you really like… I even find that blogging helps me. I just like sharing my experience and it’s one way to do so. But, nothing beats just getting out of the business routine whether it’s a sport (yoga’s my thing) or participating in cultural events (art, music, you name it).

I do try and recently tried dancing Salsa. It was nice and I got to know some people.

And then there is the fear that this might not work out. And what would I do then? Work at a job, where the boss is probably incompetent and much younger than me? And where my entrepreneurial experience is not valued at all.

– Even if it doesn’t work out as a business it will work out anyway ’cause you’ve gained so much experience. No one knows what we’ve had to endure to try and build a business and now if I was running a major company I’d want to hire people who truly understood what it took to build a company, not just some fancy degree. So, no matter the outcome, I think the outcome is positive and has incredible value.

But companies like [Big name “entrepreneurial” company goes here] think otherwise! I had a long talk with one of their recruiters. He really took the time to explain things to me: He thinks I am really smart and hard working, BUT they generally do not like to hire entrepreneurs. Instead they hire consultants and investment bankers. People that have no prior experience in startups but that are intelligent and supposedly good at execution.

Have you ever been in these situations?

– So yes, I’ve been in all of the above.

– Having said all of the above I think having a supportive environment is very important. In Startup Chile I felt really supported and I always had people I could speak to. Startup Brazil was similar but on a smaller scale. One really needs a strong supportive environment. Especially one where you can talk to other entrepreneurs. Maybe you need to go home for a few months and recharge or find a place where you can be around lots of good entrepreneurs.

I agree. I think it already helps that I have a co-founder.

– Call anytime and know that you are not alone and that what you’re going through is perfectly normal and natural.

Thanks for your advice. It is good to share with a fellow entrepreneur! 🙂

So, Keep Calm and Keep on Truckin’ – to mix two generational metaphors.

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