The Neverending Entrepreneur's To-Do List

Most entrepreneurs can probably identify with this feeling. You know, that feeling of 'to-do list defeat' that sets in the moment your feet hit the bedside floor in the morning. No matter how hard you work, no matter how hard you burn the candle at both ends, you know that you will never get through your daily to-do list. There will always be unfinished business. Over time, that unfinished business gets carried over from one day to the next and sooner or later you start feeling like a mountain sherpa carrying the luggage of a growing crew and every time you look up at the peak it just never seems to get any closer, if anything, it slowly drifts further from view.

What I've just described is a mental battle, a war that plays out in the mind of many start-up entrepreneurs, and in most cases, it's a war that won't be won or lost. Just like that old adage 'it's not whether you win or lose, it's how you play the game' it rings just as true for us entrepreneurs. It's how you manage both physically and mentally the neverending to-do list and the stress that results that will probably determine whether you are able to continue on your path, or get derailed by burnout or diminished health.

Over a decade ago I had aspirations of being a professional actor. I won't go into the long and boring details about my trials and tribulations as a young thespian, but I did receive some precious advice along the way that to this day has stuck with me. While standing in an Oxford courtyard rehearsing Shakespeare on a cold rainy evening with a tutor, I began questioning why I was there, and would I ever 'make it' as an actor. Was I crazy for pursuing this in the first place? My tutor whose name shamefully escapes me thanks to father time (I think it was David Sterling), was an older man who had been 'around the block' and seen it all so to speak. He responded in a thick british drawl with words I'll never forget...

'You're insane. Just admit it, get over it and start accepting the fact that you're totally, absolutely insane. You're insane! Nobody in their right mind would embark on being a professional actor knowing the odds of being successful. Look at you! Your lips are turning blue, you can barely get this sonnet down, you speak in a Canadian accent. Ha! Either leave now and go home a normal person, or stay here and start getting used to the idea that you're completely nuts. But make no mistake about it, the sooner you admit your insanity the sooner you will put yourself in the right frame of mind to train to be a professional actor.'

A hard dose of reality indeed, but it was exactly what I needed to hear. While I certainly didn't 'make it' as a professional actor, that reality check helped me mentally unleash the emotional baggage of worry that I was carrying around and it really helped me go on to complete my training, receive my diploma, continue to work on my craft and go on to have some great experiences in the field of acting.

So what does this have to do with the neverending entrepreneur's to-do list? Everything. Much like admitting I was insane for pursuing acting, sometimes as an entrepreneur you have to accept the fact that your to-do list is not likely to change much, by that I mean, you will always have a full list. Stop operating under the illusion that it will get shorter. As things get crossed off, more items inevitably are added. At some point, it's just a good idea to accept that, and then find ways to manage the stress. Sure, that's easy to say, hard to do. But I think the to-do list in our minds is probably weighing us down more than the actual to-do list itself. As entrepreneurs we've got to find ways to free up our mental space, even though the physical to-do list will always be longer than the hours in the day provide us to get the items done no matter how good a GTD'er or organize freak you may be. Resources are what they are, and in many cases, especially for start-ups, that's not going to change in the immediate future. Sometimes it's just accepting that the timetable is what it is can help get your mind and body unstuck from the mud of stress, worry and to-do list overkill that can plague us at any twist or turn in business. I'm not suggesting you sit back in apathy and say 'it is what it is'. In fact, it's the complete opposite. It's all about being productive and being able to continue to work crazy hard and crazy long hours. Because ultimately, that's the most important thing. If burnout or poor health get the best of you, you lose and so does your venture. By accepting the fact that despite your best efforts, your to-do list will grow longer and some stuff may not get done exactly when you had planned, it can help you roll on and live to fight another day.

Thanks to my buddy David for inspiring me to pen this post.

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The Neverending Entrepreneur's To-Do List

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