The Five Stages of Entrepreneurial Grief

For twenty years, I’ve owned and operated a small business. That entire time, I’ve also been building a career as a novelist. Which means, basically, that I run two businesses, each with their own subset of associates, fellow professionals, clients and subcontractors.

Along the way, I’ve met a lot of fellow entrepreneurs from all kinds of industries. The environments they’ve chosen for their professional pursuits are as individual as they are. Some of them rent office space. Others work on-site at the companies for which they freelance. Think bullpens, tiny offices without windows, and twice, a lopsided desk facing the wall in the hallway. (Yes, that actually happens in real life and not just on predictive episodes of Mad Men).

Most entrepreneurs, however, stake out a portion of their homes as The Formal Place of Business. Complete, of course, with The Official Business Computer, which is never, ever used for video games or downloading porn. Not because clients or a spouse would object but because the IRS would eliminate those juicy tax deductions that help small businesses stay alive.

Since that official piece of equipment is so important, there must also be an Official Work Desk upon which it can perch, a matching (or at least functional) Official Work Chair (swivel and rocker abilities optional), and various Official Desktop Corrals for pens, paper clips, stamps, lucky trolls, lucky pennies, moneybags Buddha figurines, and that collection of thumb drives containing material that will forever remain mysterious because thumb drives are too small to mark with a Sharpie.

Ah, the envy home office spaces inspire. You get to work in your bunny slippers and nothing else, people think. You can be drunk at noon and no one cares, they murmur. You can take off and go shopping, mow the lawn, or simply drive around aimlessly in your splendiferous 1975 AMC Pacer, which was a subcompact before subcompacts became a thing without the pesky gas-saving elements of other subcompacts but hey, that’s all your self-employed income will support, and so what if it looks like a gigantic squashed jellybean. It runs, doesn’t it?

Or so everyone thinks. About the whole entrepreneurial thing, I mean.

But for those who actually are self-employed, reality sets in. Not once but over and over. This, I have realized, follows a rather consistent pattern. So, before you too are wooed by the siren’s call of working naked in bunny slippers (which is surely against a bunny slipper innocence protection ordinance), do yourself a favor and review the five stages of entrepreneurial grief.

With a nod to Elisabeth Kubler-Ross, I hereby acknowledge and affirm that If there is an entrepreneur, there is work; if there is work, there is an entrepreneur.

Link to the rest here. Originally published on The Rouse, a content website for small businesses.


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