An Entrepreneur's Worst Nightmare

Don Draper: “Oh, you mean love. You mean the big lightning bolt to the heart where you can’t eat and you can’t work and you just run off and get married and make babies. The reason you haven’t felt it is because it doesn’t exist. What you call love was invented by guys like me to sell nylons. You’re born alone and you die alone and this world just drops a bunch of rules on top of you to make you forget those facts. But I never forget. I’m living like there’s no tomorrow, because there isn’t one.”

One of the biggest threats I see to the typical young entrepreneur is not one most would expect, because it doesn’t have anything to do with business.

The hardest task in going full time on your thing is commitment. There is a thousand and one easier things to do than make yourself work. You will have to learn a ton that you would never think of before you take the leap into doing what you love professionally. That can be overwhelming, so if you have someone willing to help you consider yourself one lucky SOB, because most are alone in their endeavor. Loving something is not enough motivation to get up and do it day in and day out till you can start taking weekends off. Compared to the couple of years of living an unpampered new freelancer or entrepreneur lifestyle just giving up is easy. You are stepping from the world of someone else taking the responsibilities and paying you to just do your tasks into a world where everything is 100% on your shoulders. Now the reward for that is massive, but it won’t happen overnight. When I originally wrote this, I truly believed that 99% of the time an entrepreneur’s worst nightmare was dating. First it takes your priorities off the matters that you need to take care of. (time and energy you need to dedicate to your craft) You start letting your partners, coworkers, and your dream come second, and that’s the saddest part. You start letting everyone down but your girlfriend/boyfriend. What’s worse is you won’t even be able to see that you are doing it, because it’s easy to forget when your blinded by a new fancy. The first part of a relationship lasts just long enough for you to forget why you wanted to pursue your own thing in the first place. Why do we do this? Well, for starters dopamine is a drug. Romance is the overdose. Partners want to make life easier for you, they want you to be content and comfortable. They don’t want you to ever be sad or down, and they will go to extremes to extend that moment as long as possible. This is why it’s a nightmare, being your own boss, taking the responsibility for your work ethic, and success is hard. Doing work will always be harder than spending time with someone you love, and most people can’t balance the two. Sadly, most will take more and more of the love drug until their dream dwindles and the fire for it goes dormant. When you’re pursuing something difficult it’s deeply rooted in fight or flight, and giving into the flight impulse even once is a choice most won’t ever come back from. You have to fight every day to get to your goals. This lesson was taught to me early, with my first girlfriend, and it stuck. I’m not going to claim that I never let the struggle convince me to try from time to time. I was lucky. I never made it more than a week or two before I couldn’t fight the conflicting feelings, and self-destruct the relationship. I would almost immediately start neglecting my work. I’d realise I was just hiding from the real issues, start to course correct, and get my priorities back in line with my heart. In full disclosure I’m not single. For months I told her she would never want to date me, she never listened and never left. Over time, she became someone who knew me better than even my closest friends. She saw the craziness that comes with being highly driven, she accepted that I couldn’t be with her 24/7, and she won my trust. What makes her unique in my experience is she has her own passion she is pursuing. For the first time I feel like I’m growing with someone not away from them. We have talked extensively that work and the big picture will always come first, but that doesn’t mean I don’t care for her. She is on a similar path, so I think she understands in a way most can’t. It took six years to find someone like this, and I don’t think most people put that much time into finding a good match. Thus, my feelings on the topic as a whole is unchanged.(Full disclosure over)

“Character cannot be developed in ease and quiet. Only through experience of trial and suffering can the soul be strengthened, ambition inspired, and success achieved.” Helen Keller

“Fearlessness is like a muscle. I know from my own life that the more I exercise it the more natural it becomes to not let my fears run me.” Arianna Huffington

“To be happy at home is the ultimate result of all ambition, the end to which every enterprise and labor tends, and of which every desire prompts the prosecution.” Samuel Johnson

The last quote holds the key to explaining why dating can be a young entrepreneur’s worst nightmare. Finding happiness in another person can feel very similar to true happiness, but happiness found in another is always temporary. It doesn’t fix any of the problems that made you unhappy to begin with. In essence, it’s only a bandaid. Eventually, you will realise the person you found happiness in is a real person with real flaws and dreams of their own, and you won’t be able to lose yourself in them completely anymore. Sadly, by the time that happens you may have neglected your responsibilities long enough that it’s easier to give up than start the struggle over again once you have fallen out of your network. In my opinion that’s how you die with regrets. In all honesty, isn’t that the last fear of our lives, that we will look back with regret? It’s a long game. If you stop playing early you’ll never be able to live without asking yourself “what if?”

The love game has taken many a friend. I know it will continue to happen in the future which to me is sad, because I truly believe giving up on your dream is one of the biggest disservices you can ever deal yourself. I have grown to love the game, the stress, the responsibility, the wins, and the losses. It’s fun once you start seeing that your choices have a real impact on the fabric of your life. It gets amazing when you take charge of your own destiny. It takes effort, strategy, and you have to build protections for yourself along the way. The road has many pitfalls, and many paths that seem easier at their start. There will be countless times when you get hit in the face, that’s life trying to knock you off your path. How you handle it will make or break you. In the pursuit you will find faith in yourself that you never believed possible.

If you have made it this far, and haven’t written me off as some butthurt dude that got burned and now hates love. I have one thing to ask. Please don’t give up on your dream because it’s easier to cuddle than hussle.

You can do this, you have the strength, you have the courage, and you have already made through the hardest part. It may never be easy, but in the end it will always be worth it.

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