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Your Business is Failing. So, What’s Next? 7 Reflections

Apr 28, 2020 | Business & Enterprise, Short-form

Reading Time: 6 minutes

“Running a start-up is like chewing glass and staring into the abyss. After a while, you stop staring, but the glass chewing never ends.” 

Elon Musk

Currently, there are 30 million small businesses across the United States. Or at least there were that many at the start of 2020. But with COVID, it’s likely that more than a business owner or two is yanking their hair out because their business is failing. And literally before their eyes. Or it just failed. 

Mine is just such a business. 

However, when I searched for resources to make sense of what had just happened to me… all I found was articles on how to avoid business failure. Fat lot of good those did. 

But it’s really no surprise. The expectation is so often placed on entrepreneurs to hide their pain, to fight on until they can fight no more, and too often pretend that everything is okay even when it’s not. 

And that’s stupid. 

So, today, my business failure is your gain. What did it feel like when my business was failing, what came after, and what can you learn from my experience? 

Favor for Paper Entrepreneurs 

Let’s stop for a quick detour to better understand the context of today’s business environment.  

It isn’t conspiracy theory anymore… in contemporary America, the government and its corporate class most clearly choose which businesses will thrive. And which will not. Apple, Google, Tesla. These are all companies that benefited heavily from federal help in their early days. (Although to Musk’s credit, Zip2 and PayPal were built the good ol’ fashioned way: by putting your money where your mouth is).  

But crony-favored companies like Boeing literally can’t even make planes. Would you also be surprised to find out that Netflix doesn’t even turn a profit? 

But it gets worse. 

Unfortunately, for the far majority of small business owners help is not so forthcoming. As I write this piece, the PPP loan program as well as the disaster relief program are little more than a disaster themselves. A tiny percentage of small businesses even saw any money at all. As business owners across the US worry if their business is failing, they’re also forced to frantically compete at games with their banks. 

But quietly, on the sly, banks and corporations, entrepreneurs on paper only and businesses simply by decree, are getting untold sums shoveled to them overnight without any questions. And very few, if any, strings attached. So, today, it doesn’t matter if Netflix is a failure; they grow. 

Now imagine, how that must feel for a small business owner. You’ve put, in many cases, years of your life into your small company. Often, plenty of money has been reinvested back into that dream. And now you have to play cash grab for crumbs while the well-connected are lavishly provided for. 

Truly, this is the age of paper entrepreneurs and zombie businesses, not of real business owners.  

Why is All of This Important to Know? 

For you business owners, you probably already know that starting a company isn’t for the faint of heart. In every case, it’s also an individual journey with lessons learned and visions fought for. Those journeys can be deeply personal, so much so that many entrepreneurs struggle to separate their personalities from their business endeavors. 

Of course, I’m no different. Born from a desire to “do it better,” I set off on a road that I would never have guessed would take me to where I am today. After nearly a decade and considerable growth, I can count myself among the lucky minority that have owned a successful, growing small business. 

The operable words here, however, are “have owned.”   

What would have happened if the government hadn’t screwed up the financial system? Or locked-down the entire damn economy for what appears to have turned out as a nasty flu? And what if they didn’t shovel money to their friends?

Although it has never been easier to start a business in history, it’s also never been harder to make one successful. 

And we’ll never know the answers to these questions. Yet, what we will know is that after considerable small business success and a hefty amount of operational savings in reserve… I looked at myself and made a very difficult choice.  

It went something like this: “After close to a decade, my business is failing, and we likely won’t survive the shutdown or what comes after. Do we burn through our operational savings or do I close forever?” 

It is not an easy decision. And in most cases, you have no idea what will come after. 

What Comes Next: 10 Reflections if Your Business is Failing 

For those of you reading this who are fearful that your business is failing, and you’re concerned for what’s on the other side, I’m going to share a few reflections from across the divide. My business experience isn’t indicative of everyone’s. Still, at the very least, hopefully these can act as guideposts in your journey, however it goes. 

And to remind you that others are going through exactly what you’re going through. 

  1. You’ll be relieved that it’s finally over. 

If you’re like me, you might have come to terms long ago that there might be an expiration date on your business (and I suggest every business owner foster this mindset). And now that it’s done, the plate juggling can stop.

Entrepreneurs are often magnificently overwhelmed with an array of concerns so big it would make a corporate manager’s head spin. And when your business is failing, you suddenly realize that huge burden… is simply gone. You’ll feel slightly guilty that it is (since most business owners report feelings of guilt even when they’re in business). 

Yet, for now, you can take a deep breath and reflect. 

  1. You’ll feel better if you definitively make the decision. 

Now, nothing says your business entity can’t partially live on until new lands are in sight. However, you’ll gain far more clarity if you’re decisive about this being the end of the road, if your business is failing for real. Look at the numbers and make the call.

Too often as entrepreneurs we have to live with uncertainty, but at least this time, the decision to be done is within our power to decide. Don’t let this one linger, even if it is one of the biggest decisions you’ll ever make. Do yourself a favor, and when it’s time, let it go. 

  1. It will be difficult to share your experience. 

Let’s be frank for a moment. I’m friends with plenty of executives, middle managers, professionals, and politicians. And they most certainly don’t know the first God damn thing about owning a small business, no matter what nonsense they believe.

Zero. Zip. Nada

You, on the other hand, probably truly know what it means to grind your way forward. Or to wear every hat in the book. That comes with unique experiences (and unique skills). In my opinion, only other entrepreneurs can really appreciate what you’re going through. Seek them out; talk to them. 

  1. You’ll question your abilities, your experiences, and your confidence. 

You might laugh, but I’ve been described as a megalomaniac on par with Captain Ahab himself. Although I’m always surprised by it, I’m often asked how I got so incredibly confident or how I’m so comfortable with uncertainty. And I pride myself in my ability to not only bounce back but be a glutton for pain as I continue forward when no one else will.

Still, when your business is failing or has finished its run, you wonder if it was all worth it. And also, who you are now as a result of it all. Can you really bounce back from this? Of course, the answer is “yes,” and so much so, you’ll be able to do so better than most other people. 

  1. Everyone will want to know what you’re doing next. 

You can’t fault the “normies” for immediately wanting to know what’s next for you. After all, many of them hop jobs every couple years and act like owning a business is a fun hobby. Well, they’re definitely going to ask you, even the day you decide to wind down your small business, about your next step.

Most won’t be curious why you had to do it or what it was like… all they want to know is, will you be successful again? My advice is to make up something outrageous like how you plan to take up trekking the Amazon to find yourself again. 

  1. You’ll have sharp focus on who was on your journey with you. 

In our culture, entrepreneurs are given a somewhat mythic status. Research has even concluded this to be the case. You know what I mean: the respect that comes with being the master of your own destiny when you own a business. 

Still, when you discover your business is failing and soon after, you’ll be reminded of who was there alongside you and who wasn’t. Since I’m someone who likes to know a large diversity of people, I’ve been rather amused by how many people feign friendship but never asked anything about one of the biggest undertakings of my life. And we’ve seen how these are the people to distance yourself from

  1. You’ll review your options knowing you can do whatever you want. 

Even though I could probably serve up many more of these, I definitely want to end on a positive note. When a business is failing, it can be heartbreaking. As your entire world is changed in the blink of an eye, you can’t help but want some answers. Will corporate hiring managers understand my experience if I apply for jobs? Should I start another business? Do I have to start all over no matter what new direction I choose? What good was all this networking I did?

These questions are largely a distraction from the reality of your situation.  

Unlike someone who loses their job and sits around for the next six months feeling sorry for themselves, your business experience has made you a person of action and enterprise. And a person who knows what’s truly possible.

Even with the odds so completely stacked against us, we’ve built things, we’ve grown, and we’ve owned the day. There is a power in that that so few others can understand in this day and age… or who can put to work again.  


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