The Entrepreneur's Dilemma
Although sometimes overly glamorized and under-understood, it is generally accepted that being an entrepreneur is hard.
But what is often less talked about is what exactly is meant by the term "hard" and exactly how one qualifies as an entrepreneur. Do you have to succeed? How big to you have to build something? Do you have to take funding? Do only certain types of business and experiences qualify?
Although these topics vaguely rattle around in my head every so often, I started considering their meaning and impact at a deeper and more focused level when I caught Andy Ellwood's compilation of Shakil Khan’s tweets on the subject of hard work and entrepreneurship.
As a result, I felt compelled to share more widely my thoughts below and hopefully more in the future (the goal being part personal catharsis, part to serve as support and counsel for those in a similar situation, or thinking of taking the plunge and sticking it out).
Shakil’s first two [1,2] tweets were particularly inspiring and serve as a great interlude to my post below:
“I actually think most folks are obsessed with the IDEA of being a startup founder/ceo, rather than wanting to do the ACTUAL hard work. I also think quite a few just want to be known as Entrepreneurs or talk about startups & how to build a business, rather than doing it.”
So Andy and Shakil, thank you. Also shout out to female founder powerhouse Ellie Cachette, whose writeup about her recent talk at Yale also pumped me up. And thank you to everyone else who has inspired, supported and contributed to what I am about to share.
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The Entrepreneur's Dilemma
Starting a company is hard. Keeping a company going is hard. Working a fulltime job at the same time you are running your own company is hard. Doing that for three years is hard. Quitting your fulltime job and just running your own company is hard. Doing that for three more years is hard.
Competing for business with companies that have 5x, 10x, 100x your staff, process / system efficiencies and resources is hard.
Competing with these same companies when your company, staff, processes and systems are still being built and stabilized is hard.
Adjusting to changing demands, landscapes and resources is hard. Self funding is hard. Cashflow is hard. Deciding to make sacrifices that take a toll on your health, your family, your loved ones, your sleep and your diet is hard.
Not quitting is hard. Staying after it for 70 months -- nearly six years -- like I have is hard.
Finding the right talent is hard. Keeping the talent is hard. Recruiting is hard. Training is hard. Firing is hard. Making the wrong hire is hard. Saying goodbye to talented team members is hard. Bringing in new people to replace them is hard.
Overcoming obstacles, haters and challenges is hard. Biting your tongue when all others are flapping theirs is hard. Keeping your head about you while all others are losing theirs and blaming it on you is hard. Saying “no” is hard. Executing once you’ve said “yes” is hard. Being in the trenches is hard. Leading is hard. Throttling between the two is hard. Doing everything yourself is hard. Delegating is hard.
Starting a company with your significant other is hard. Approaching things differently than your significant other is hard. Working through those differences is hard. Hiring and then being the boss of friends is hard. Learning to work with and trust complete strangers is hard.
Failing is hard. Learning from failing is hard. Doing good work is hard. Continuing to do good work is hard.
Traveling for days -- weeks even -- on end is hard. Sleeping in different hotels, napping on different planes, moving across the country and trying to stay on top of everyone’s demands on your time is hard. Being at the end of the line is hard. Being at the front of the line is hard. Being in the middle of the two is hard. Coming up with big, creative and successful ideas is hard. So is delivering on them. So is not delivering on them.
Trying to work on the road is hard. Trying to exercise and eat right on the road is hard. Trying to work at a long table with a bunch of people in one room is hard. Taking Skype calls with spotty wi-fi is hard. Taking conference calls from Starbucks is hard.
Working with team members in different offices and time zones is hard. Working with team members with different backgrounds and viewpoints is hard.
Working with older generations is hard. Working with people your own age is hard. Finding time to thoughtfully reflect, write and relax is hard. Finding time to give back and to stay informed is hard.
As I prepare to celebrate my sixth year with j3 in September, I’ve come to accept and embrace that there are very few things that are in fact easy about what I do at j3. But I guess that is why I love it. Each “hard” has taught me something, strengthened me in some way and prepared me for the next -- Lord help me -- even harder challenge.
And I guess there is a beauty in giving yourself so wholly to something. When you believe in it through the ups and the downs; when you believe in the people who have contributed just as much as the people who continue to contribute; when you believe in the vision of building something special, unique, somehow better than what existed before you entered the marketplace.
It is as much an act in fidelity, as it is an act in faith.
It is as much an act in perseverance, as it is an act in hope.
Stepping back for a minute, as I re-read my description of “hard” and the related challenges I’ve faced, long burns I’ve endured and extreme conditions I’ve survived you would think I was talking about being in a war or surviving some sort of traumatic thing. Thankfully, mine was a choice to experience extreme conditions -- and first world ones, at that. Most people in the world don’t have a choice and their “hard” is often life-threatening, inhumane and uncivil. My “hard” is in fact a choice and a gift and a drive that I’ve had since I was little.
Starting j3 was hard. Keeping j3 going is hard. But I was built for this. I was raised with a strong sense of self, work ethic and faith. As the Chinese Proverb says: Out of the hottest fire comes the strongest steel.
And so, to all of things that are hard, I say: Bring. It. On.
Author’s notes:
Originally posted on my Tumblr, The Entrepreneur's Dilemma [June 30, 2012]
Image source via Andy Ellwood’s Tumblr here.
Where I could in this particular post, I cleaned up the links to connect to the modern URLs where available [as of August 16, 2025].
I was so moved by my writing, that I am drafting it as a post over on Medium. Plan to publish it later in August 2025. (so if you are coming from there, welcome back to the future ;)
