What Happens After the Worst Happens
Before my husband and I started Wholesale In a Box, I ran a small coffee-related social enterprise called Liga Masiva — which led me to an exclusive 10-week startup incubator called The Unreasonable Institute. One of the first workshops was with a facilitator named Joy Anderson, and while she shared a lot of fascinating ideas, the moment I've never forgotten is when she asked if anyone had fears about their startup.
Diego, a dashing, confident guy from Latin America raised his hand and said quietly that he was afraid his company could get sued. The room got quiet from the rapt attention of a group that empathizes with the question. I think we were all waiting for the facilitator to reassure him (and us) that that was very unlikely.
But Joy looked straight at Diego and said: “You will. If you have any success in business at all, you will get sued, likely multiple times.” She went on to say that she had been sued several times and that it’s just the nature of having an entity that is so visible and interfaces with so many people with different expectations.
What Joy was really saying — and what took me a while to fully understand — is that most of us carry around a vague idea of "the worst that could happen." And because we never look at it directly, it has power over us, perhaps even guiding our decisions on an unconscious level. But the way past this isn’t hoping or reassuring ourselves that the worst is unlikely to happen. Rather, it’s to accept that it probably will… and that we’ll be fine regardless.
I’ve thought about this a lot over the years, especially because for me, the “worst” has happened in my work in many different ways, in different ventures:
A competitor completely replicated our software (in the original version of Wholesale In a Box), slapped a different name on it, and then marketed the crap out of it. (Eventually their business closed but it never mattered anyway.)
When I ran the coffee social enterprise, a local restaurant stole our logo and used it on a 6-foot awning on their building. When we confronted them, the owner said "Well what are you going to do about it?"
… And many small examples of customers or partners or random people being mad and basically saying words that flutter around our nightmares: I don't like you. You made a mistake. I'm going to tell everyone.
In fact, just the other day I emailed someone to ask for input about a potential project and she emailed back something to the effect of “I don’t like the idea and this reminds me – I didn’t like how you handled the last thing we worked on together.” The worst nightmare of an email response, right?
I feel I should say that the vast majority of my experience has been the opposite of this — full of meaningful relationships, people I'm still close to, work I'm proud of. If you could somehow quantify everything that has "gone terribly wrong" as a percentage of my total business experience, it would be .00001%.
Be that as it may, I still think it’s worth accepting that the worst will happen when you start a business. And the incredible reality is that it won’t matter nearly as much as you think it will. People will take your ideas. They’ll publicly shame you. They’ll correctly identify an idiotic mistake you made. They’ll be mad at you on a very personal level. You’ll make mistakes that you later realize were really dumb and never do again but won’t be able to erase the consequences of doing them in the first place. You’ll lose large amounts of money.
And… you’ll keep going. Meaning that even as the “worst” happens, you’re still pursuing your dreams and doing work you love and supporting your family and becoming stronger as you go.
Of course, we can reduce true risks, especially risks that would end our ability to run a business or threaten the health and wellbeing of our family. I'm not really talking about those. But when we imagine the horrifying scenarios, they're usually more emotional in nature — being shamed, stolen from, copied, ignored, hated. And the good news is that we can simply accept that those things will happen. And accept that they won't matter nearly as much as we think they will.
Because happiness and character and freedom aren't about having an unblemished record. They're not about never making a mistake or never experiencing pain. They're about being someone who can hold all of that and walk your path regardless. The Stoics had a practice called memento mori — contemplating your own death as a way of clarifying what actually matters to you. Accepting the worst in business works the same way. When you stop hoping the hard things won't happen, you stop living in fear of them. And that's when you're finally free to build and live in the way you want to.
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