For most people the holidays are about family, escaping work, overindulging on food and drink, and generally checking out. Those with jobs as teachers, bankers, and mechanics put their work lives on hold for a few hours or days. But for entrepreneurs, that’s not possible. Depending on where they are along their entrepreneurial journey, this time of year can be any combination of suffocating, exhausting, or jubilant.
For the lucky entrepreneur, who has found some measure of success, the holidays become a personal victory lap where friends and family tell her how smart she is, how proud they are of her, and how they always knew that she would do something great. These are the good times. This is what we all strive for.
But that’s not how it goes for most entrepreneurs.
For the wantrepreneur or the still-toiling-away-at-the-drawing-board entrepreneur, time with family typically amounts to justifying her life and career choices, explaining the genius behind her billion dollar idea, and generally avoiding questions about “getting a real job.” These are stubborn times.
For the entrepreneur who has found that breakout idea, the holidays turn into a never-ending pitchfest for that oh so important friends and family (and fools) round of funding. Everyone with two nickels to rub together becomes a potential investor, and everyone who was once a mid-level executive becomes a potential advisory board member. These are optimistic times.
For the entrepreneur who raised that friends and family round in years past, the holidays are akin to a board meeting, “Groundhog Day”-style. Every family member who wrote a check needs an update. If things are going well, this is a labor of love. Our founder shares details on her current product roadmap, recent business development wins, new hires, fundraising status and valuations, and all the wonderful things the press has had to say about her company since the last update. These are hype-filled times.
And when things are not going well, this never-ending board meeting becomes death by a thousand paper cuts. Every “investor” (read aunt, uncle, grandfather, neighbor, t-ball coach, and mailman) who backed the company – most who presumably haven’t seen the entrepreneur in months, if not years – wants “an update.” What they really want to know is “What did you do with my thousands of dollars and how ‘gone’ is it, really?” Often, this will be the first time most of these investors hear the naked truth, or more accurately, see the painful reality of that truth in the entrepreneur’s eyes. These are crushing times.
Finally, for many entrepreneurs, the holidays are a lot like every other day. Rather than consisting of some long pilgrimage home and time spent with loved ones, the holidays are spent toiling away, probably in front of a computer screen, hoping to make a dent in the mounting list of to-dos, but surely nowhere near a fireplace, a turkey dinner, or any eggnog. These are lonely times.
There’s a reason investors and fellow entrepreneurs ask those starting out in this game whether they’re ready and willing to dedicate several years of their life to the all-consuming pursuit of a startup dream. It is the most relentless and unforgiving of quests.
So if you have an entrepreneur in your life, remind them this year to put work away this holiday season. And if you were part of a friends and family round, maybe leave that fact at the door, at least until your entrepreneur has gotten a few glasses of eggnog under their belt.
If you are an entrepreneur yourself, remember why you got into this game in the first place. Rediscover a bit of that sense of excitement and possibility from a time when failure seemed impossible.
And most importantly, put family before company. The hustling, disrupting, and non-stop selling can wait, at least for a little while.