Almost Reckless????????

Really? What if ….. not taking the risk is actually the risk?

I’m reposting this - with a few edits. I wrote this early in 2024 and wanted to reshare. Anything that is older here is placed under a paywall, so I wanted to pull this one out. For a reread or new read, as you wish.

Taking risks and making bold decisions I tend to find easy, I’ve always had a strong intuitive gut in that way. But sticking with them, not obsessively questioning them or worst, reverting course, that’s a different subject. It’s not as simple as arming yourself with data that your decisions were right. Even when the data is in your favor, is not easy. The urge to look around you and step in to line when your ideas and actions are wildly different can be incredibly tempting. It’s why you see many companies or individuals come on to the scene strong based on the naive rawness of their individuality - only to later conform to a common banality that can make them barely recognizable from their peers. It’s one thing to make mistakes and go back, understand how and why they happened. And it’s another to make them knowing you knew all along what the outcome would be, and that somehow along the way you hoped it would be different. The latter sucks full stop. We all know that uniqueness, a point of differentiation, is the holy grail and that the absence of it is the ordinary. so what gives here? Why do we start to doubt ourselves, even in the face of indisputable success? Is it because when the stakes get bigger there’s more to lose, so much more at risk?

The idea I’m exploring here is logically put:

First, if you don’t take risks you’ll stay stagnant. But this would require writ large our friends and the world to conspire to do the same, and this will not happen. You know this, right?

Second, let me state the obvious. And then a second obvious. Taking risks can be frightening as you can not be certain of the outcome. We can never be certain of any outcome.

Third, when risks are rooted in pragmatism or simply what you know to be right, the outcome will always sit right by you from the perspective of integrity. And since at the end of the day, truly all we have is our body and who we are as individuals, there is a sound argument that if both are healthy we will have security in this path.

“Man, then, when he comes to a decision, cannot ever be sufficiently prescient nor can he wait until logic affords him absolute certainty. If he waited for that, we would never come to a decision; he would remain in a state of inconclusiveness.”

- Josef Pieper

It may comfort you to know that I write with lots of experience as the founder of a small business that has stayed privately owned and self funded for over 27 years now. The last few years have been our most successful by any measure. Not because we hired a new lead designer to make better and more innovative designs (our designer has been with us for some 18+ years now), not because we brought in a new CEO or President (24 years and 12 years respectively) or because the global retail environment became more viable for smaller fashion brands (hardly). It was because we took what would be considered very bold risks, risks anyone in the business of fashion would have thought not just reckless but destructive.

Now here’s the thing, the idea to take such bold risks wasn’t part of the long term plan. Our hand was forced in March 2020 to make quick survival decisions - at the time we were a company generating around $60mm in annual revenue with just under 100 employees. In the span of 48 hours (on March 16 to be exact) we assessed our cash position and what we would have to do to cover expenses over the next 12 months when we felt we, the world, would be in a more normalized position (laughable to think of that now).

Teetering on the edge of the cliff made decisions much easier to make. First, take a fucking step back. Right? Then find the area that gives you stability. When you’re on the brink, you’re not thinking about where others are finding their solid ground, you’re focused on doing what is best and right for you and your company. Nothing will crystalize more in these moments how irrelevant all the comparisons can be, how what Net-a-Porter, a super funded DTC label, or a highly publicized nepo-baby brand is weathering the moment. This is about you, your people, your company. Taking stock of what you’ve got, determining what you have to have, and filling in the gaps to get there. Brutal pragmatism.

And this is where the interesting long term challenge revealed itself. It wasn’t as much about KNOWING what was right to do in the time of crisis as it was having the stomach to keep doing it. That’s crazy, right? Why is it that when we do something great, based on what we logically know to be true, that upon success we question it, look over our shoulders, waiver? And sometimes just step back in to line with everyone else.

This is where our heads and our perceptions can really fuck with us.

It’s no secret that Tibi’s always been the underdog. Was it because there were no headlines in trade publications about our success that I question our actions even in the face of great results? While this has been true sometimes for me, what I’ve come to realize is that this lack of attention fuels me, I’m someone who closely guards my upbringing, the public school I went to and my time bagging groceries, as where I derive my strength. For many, the lack of recognition alone is something that can really trigger self doubt. Understand this about yourself so you can address the real problem (your self esteem).

Do we waiver on sound decisions because of the beating drums of online pressure and current narratives? No one’s immune to this - forget being in the public eye, just simply being an average high school student can make you a target here. The summer of 2020 tested anyone’s resolve. I remember getting trolled demanding I post stats on the diversity in our company. I panicked, I got the numbers, and sat back and thought “wow. This is fucking impressive” Through no intent other than hiring the best people for the jobs, we look like the UN. I met with our team leaders to discuss what our “proof of diversity post” would look like to tell people who we our team leaders “are” - Chinese, Czech, Peurto Rican, Turkish, Black American, Vietnamese, South African, Indian, and a White American. And that’s when our President Elaine said “who are we? We are people who live our values every day and we show them through our actions. We are not people who post about it and defend ourselves to unknown accusers.”

I never made the post defending the diverse make up of our company. And later, when some came after me, I separated the trolls from those who were truly seeking affirmation that they were supporting a company they could get behind. The trolls I blocked; and those with positive intent I took the time to explain in a private dm how we believed walking the walk was better than talking the talk. Or posting the post, as it were.

This is when we knew that if we put our heads down, did what we knew to be right, that it would lead us in the right direction, always. When we can defend the decisions we make, when we understand why we do the things we do, the blueprint for the future will unfold naturally - irrespective of what anyone else around us is doing. This applies to decisions around the product we design, the quantities we make, the stores we choose to do business with, and the people we hire.

Here’s an apropos analogy. As told through a style story.

A close friend texted me before an important event. She knew what she was going to wear, but an hour before the event my phone lit up “help. I think I’m overdressed. I’m second guessing my long dress. I’m panicking.” This was followed a minute later with “nevermind. I just added an olive green sock to my sandal. I’m all good. Heading on to the stage now.”

No one in the audience could see her olive green sock way up on the stage. But somehow, going through the mental act of figuring out what would give her a little more chill, reminded her of why she had made all the decisions she had made for that night. It wasn’t about getting it right or wrong, as determined by others. But rather the security and resulting confidence you have when you know the solid rationale behind the choices you’ve made.

We’re going on four years here at Tibi where we’ve been aggressively forging our own path resolute in the knowledge that by doing what makes sense pragmatically and creatively for us as a company is the only way to create a universe for ourselves that is truly individual and authentic. It’s why I see us as a very young company, rather than one that 27 years old implies. In business, you’re never too old to change, and if you do, you may never get too old. See how that works?

No matter a company, or an individual, it holds true that taking risks in life is imperative. The risk to do the diligence to drill deep and understand what you believe in and why, continually question it in order to validate it, and then believe in the results regardless of where others are headed seems logical because it is. Doing it, however, not so easy. The sense of freedom you feel when you can do it with an almost recklessness but at the same time an odd sense of security in the knowledge that you won’t necessarily know the outcome is exhilarating, to me. It’s no different than skydiving with a parachute, no that I’ve ever done that, but it seems to me the sensation would be the same. Because the lens through which I view it is that not knowing the outcome is, in a way, knowing the outcome*. It’s just setting your expectations and buckling in for the ride.

*side note here. When you can say it, say you don’t know, or say what something is rather than what it is not, it expands your ability to communicate. It’s why I coined the term Creative Pragmatism to describe our personal style. Frustrated by the one dimensional words to describe style (you know the types: sexy, edgey, modernist), I was in search of something that would describe someone who has complex thoughts, is experimental, and has a life that requires a lot of funcitonal considerations. Someone who doesn’t reside in the extremes but at the same time is certain that the grey area in between does not indicate ambiguity but rather confidence and certainty. Giving the grey a name gave me the tools to better communicate, it turned out, not just about style but who I am as a person and as a business founder and entrprenuer.