The hitchhiker’s guide to entrepreneurship – parallels that matter


To be an ever-successful entrepreneur, one should, like a hitchhiker, stay obstinate about achieving the milestone and reaching the destination. Your guide to entrepreneurship. 

To me, the parallels between hitchhiking and entrepreneurship are extremely evident. Both involve an adaptable yet independent journey that is fuelled by passion and accompanied by freedom, risk, decision making, consequences, and ultimately, the reward of reaching the milestone. In both hitchhiking and entrepreneurship, progress relies on seizing an idea, taking the first step, having the persistence and resilience to keep trying, having a bit of luck by your side, and the ability to make the best of the relationships you form on your journey.

Having hitchhiked from the early age of 16 and being an entrepreneur at heart, my experience has helped uncover some similarities between the subjects. I have always felt that the learnings from hitchhiking can best be practised on the entrepreneurial journey, and so I’m going to try and share my experiences. So let’s put our hitchhiking shoes on and start this fascinating journey that will quench our thirst for wanderlust. Should you feel lost wandering, do not worry, for

“Not all those who wander are lost.” – JRR Tolkein

Being stubborn pays, as does being open-minded

“One of the best paradoxes of leadership is a leader's need to be both stubborn and open-minded. A leader must insist on sticking to the vision and stay on course to the destination. But he must be open-minded during the process.”
 – Simon Sinek, Best-selling author, motivational speaker, and marketing consultant

As I walked the winding road and hitchhiked my way across the rough and sometimes merciless roads of our country, I learnt one of the most important lessons: being stubborn.

Being stubborn has helped me achieve my milestones both on the road and away from it with my entrepreneurial ventures. A stubborn man is not the one that drinks from the well of bitter ego and stays inflexible in the journey, no matter what the situation. It is the man who is patient like a monk and yet, like a warrior, relentless in his efforts.

Back in 2015, I was hitchhiking from my hometown Indore to Dharamshala. It was a long, seemingly never-ending road, and it was a long time before I found someone who could give me a lift. The water that I keep carrying and refilling on the go had finished and as the road progressed, I saw no place where I could replenish it. I was exhausted and hungry, but all I could think of was the place I wanted to reach.

I kept myself motivated by the number of miles I had already travelled and focused on making plans about what to do when I reached my destination. These thoughts fuelled me and pushed me towards my destination.

There is no journey without hurdles, and at times, the body is tired and it is challenging to trick it into keep going further. I have to keep an eye out for something suspicious, be it an over-friendly person who offers me a lift or a suspicious group of hippies, so I have to plan escape routes as well.

At times, it is even the people who are either disinterested in giving me a lift or mock me for it (which truly baffles me). For every 20 vehicles that pass me by, 10 slow down, and it is ultimately one who agrees to help me and get me a little closer to wherever I am going. The probability of having a passerby stop and help me out is very low. But, even with such low probability, I always make a conscious effort to keep my mind and heart motivated to stay stubborn, not give up, and ultimately meet my objective of reaching my destination.

When it comes to business, one needs to be equal parts stubborn and headstrong.

When you start a business, everyone will have an opinion about who it should serve and how it should serve them. They will be skeptical about your plan and give opinions like “the market may not be right for you” or “there may not be a market at all.”

Stay stubborn and push through

It is easy to succumb to the peer pressure and give up. In such a situation, stubbornness will be your only ally. Stubbornness will keep you from giving up and will motivate you to pull yourself out of a critical situation. Steve Jobs was one such stubborn leader. But, if he hadn't been so unimaginably stubborn, the world would have been a meaningfully different place today. For instance, some "experts" believed Apple should ditch the Mac and start building fancy Windows PCs — a strategy that could have helped the company's financial position and bottom line in the short run but would have snuffed out the iPhone and iPad before they even existed. And thus, the world would have been a very different place right now. If you are reading this on your iPhone, iPad, or Mac, you have Steve Jobs’ stubbornness to thank for it.

Thus, an entrepreneur needs to pick, absorb, and implement this trait from a hitchhiker to pave his path of success and have his venture see the shining light of day. To be an ever-successful entrepreneur, one should, like a hitchhiker, stay obstinate about achieving the milestone and reaching the destination.

Taking things one day at a time, one mile at a time, one pitch at a time

For the uninitiated, the road to hitchhiking can be long and ever winding. With every step, the hitchhiker is one step closer to his destination but also one step away from where he began. This can be a scary notion on the road. To enjoy the journey he has begun, a hitchhiker needs to take the road one mile at a time. This helps him focus on the more important aspects of the journey. A budding entrepreneur too can feel overwhelmed when it comes to initiating the startup, be it making a pitch to an angel investor or making the first sales call. Thus, focusing and working towards smaller goals is crucial to the success an entrepreneur is looking for.

Have a 360-degree view

Assertiveness and awareness can help both a hitchhiker and an entrepreneur in ways they themselves cannot at times fathom.

It’s not always the best idea to keep looking forward and lose sight of the road left behind. An entrepreneur needs to be aware of what’s coming towards him, and what he has gone through. He should be assertive about both his competition and his own team. Thus, having a 360-degree view of the road and on the journey of entrepreneurship can help a competent leader turn into a great one.

Gratitude is the flame that lights up the darkest path

No one will ever truly know the importance of a man with four wheels better than a man with two legs looking for a lift. If it were not for every single person who gave me a lift, I probably wouldn’t have been where I am now. A true hitchhiker is thankful to every person who helps him in his journey and the gratitude helps him meet newer people with the same optimism. Similarly, an entrepreneur should value and be thankful to his peers, his team members, and even his competition.

Light of gratitude

A small venture is better than no venture; a small getaway is better than no getaway

If any hitchhiker is asked how he started his journey, he would give you the simplest and yet truest of answers: “one step at a time.” One needn’t have the fanciest of hitchhiking gear to start with their journey. A pair of rough shoes, a bag filled with utilities, and an unwavering determination is enough to start a journey. An entrepreneur needn’t have huge capital as he takes the first plunge. An idea, the will to execute it, and the patience to wait for the right opportunity to grow is enough. Rome was not built in a day, and neither was a great entrepreneur.

Hunger for calculated risks

Being safe is overrated. It is also a double-edged sword to both a hitchhiker and entrepreneur. You can never grow if you don’t get out of the comfort zone and take risks. Nothing beats the exhilarating feeling of touching the base point after taking the risk of choosing the road less travelled. It is crucial for an entrepreneur to trust his instincts and take a risk if he thinks it will help in the long run.

Take risks

Keep the paranoia at bay; trust yourselves and those around you

There is something that absolutely needs to be said and which every hitchhiker will confirm: there is unlimited niceness in this world, and it should be appreciated by trusting those around you. For an entrepreneur, trust is the key. He needs to trust people to do the right things for the right reasons.

Believe in yourselves and the world will follow

As a hitchhiker and as an entrepreneur, you should be driven by self-belief that will fuel you in getting to your destination and achieving your dream. Trusting yourself will help you sell your idea to a fellow hitchhiker or potential investor. A smile on your face and positive belief in your heart will do wonders in how people perceive you and also how you perceive yourself.

Pride is a liability and shamelessness an asset

We often forget that shame has a purpose, and if used the right way, can help us get closer to our set milestone. If a hitchhiker feels ashamed at asking for a lift, he can never reach where he intends to go. This also applies to entrepreneurs.

(Disclaimer: The views and opinions expressed in this article are those of the author and do not necessarily reflect the views of YourStory.)


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