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Month: February 2021

Crippled CEO Blog #071: Why I Imagine My Brother Dying

Crippled CEO Blog #071:

“What is quite unlooked for is more crushing in its effect, and unexpectedness adds to the weight of a disaster. The fact that it was unforeseen has never failed to intensify a person’s grief. This is a reason for ensuring that nothing ever takes us by surprise. We should project our thoughts ahead of us at every turn and have in mind every possible eventuality instead of only the usual course of events.”

– Seneca, Letters from a Stoic

A few times per week, I convince myself that my brother has just died. I imagine it thoroughly. I make myself really upset.

The reason for this is counterintuitive. I do it because I want to be happier.

And you are right, this doesn’t seem like a happy thing to do. In fact, it seems like it would make you quite sad. And it does, temporarily. But that’s the point.

However, there are three things that this exercise does that end up making me happier overall.


After I’m done, I obviously remember that my brother really isn’t dead. Focusing on something terrible that hasn’t happened makes me better appreciate many of the good things that I might take for granted. Also, if I get myself to really feel like something legitimately tragic has happened, I get some of the same benefit people get from an actual tragedy: your perspective shifts to realize what’s really important, how great life is, and what trivial BS most of my “problems” actually are. 

Last week, it looked like we might lose our largest customer in the worst way possible. Not only were they going to cancel the $1 million+ worth of orders that they had placed for the next couple of months, but they were also going to send back the hundreds of thousands of dollars worth of inventory they had already purchased this year. This is not the way I wanted to start the year after the pandemic.

And while I did treat this with the gravitas it deserved and made it a top priority to resolve — lots of people’s livelihoods (including mine) depend on my ability to successfully navigate these kinds of existential threats — I don’t think any of the people who were working on this closely with me would say that I panicked or was otherwise freaking out. I was focused on it when I could make progress, and I thought about it often, but I wasn’t completely consumed by it. We got lots of other things done last week. And eventually, we got everything squared away. Crisis averted. I think one reason why I was able to keep my cool was because this “emergency“ was nothing in comparison to the visualization that I forced myself to have that my brother had died the day before. Next to that, this is no big deal. It’s just revenue that we can get back later. I was able to put something legitimately serious into the proper perspective in order to stay calm and address it thoughtfully and rationally. 


Making yourself feel these emotions gets you used to experiencing them. It’s training. And like most training, it sucks and it’s painful, but the more you do it, the better you are at processing those feelings. 


Not only are you training for the emotional impact, you are also training yourself to handle events like the one you imagine. If you think through everything you would do if you lost your job, if that were ever to happen, you would be more prepared. Not only would it be less of a shock emotionally, but pragmatically, you would already have some ideas of what steps to take — steps you decided on at a time when you had more clarity, not suddenly thrust into this surprise emergency. 

Avoiding negative feelings, hopping from one happy moment to another, seems like a happier way to live, but it is building a foundation made of sand. You need to visualize the worst thing that could possibly happen, really put yourself in the situation, to create a more solid foundation for happiness, and to give you the tools to move forward with things when they go wrong, as they always do. 

(Did you like that? Your mom liked it. And it’s not the only thing she liked. I text her every week, normally late at night, and I could also send you a text every time I post the newest blog. Send a message to 484848 with the word CRIP as the message and you’ll get a text from me as soon as the latest one is up. Also, tell your mom I’ll see her later.)

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Crippled CEO Blog #070: When I Panhandled for Change

Crippled CEO Blog #070:

When I was in seventh grade, my electric wheelchair was dying.

Growing up, my chairs would last around five years before they were just breaking down all of the time and too unreliable to keep using.

This chair was on its last legs (or wheels) with a gang of quirks and idiosyncrasies I had to navigate to make it through the day. 

Unfortunately, power wheelchairs are expensive. The price tag on the chair I was going to get next was about $12,000. Insurance doesn’t help. There is no government support. We were responsible for the entire thing out of pocket.

And my parents didn’t have anywhere close to that much money to spare.

So, in the weeks leading up to Christmas, I took a Folgers coffee can with a hole cut in the lid, taped a label to the front of it that read “Eric Lupton’s Wheelchair Fund,” and parked myself outside of Walgreens. Even at 12 years old, my extroverted, salesman nature was already developing (a trait that has receded over the last decade or so, I think), and I engaged every single person that walked outside of that Walgreens. I didn’t ask them for anything. I just said hello, smiled, and asked them how they were doing. And over and over again, people put money into my can. I did this every day after school, a few hours a day, and all day Saturday and Sunday. After a week, I figured out that I was making about $20 per hour, which was pretty incredible. Even at $20/hour, though, it was going to take me 600 hours to reach my goal. We were only a couple weeks away from Christmas, and we expected the donations to evaporate once the holiday spirit expired. I wasn’t going to make it. 

My dad had a mailing list of all of his pool fence customers, and he sent out a letter to each of them — telling my story, explaining how I was trying to raise money for this wheelchair. The response was great, but we were still a long way off from our goal. 

I kept doing the Walgreens thing. Day in, day out. People gave change, or $1 — some gave a couple dollars. And some truly generous people would me give a $5 bill. 

Then one day, this dude, in a hurry, slides a $10 bill into my can. I’m stunned, and before I can thank him, he’s gone. I kick myself for not responding faster, and the guilt ate at me for the rest of my shift. When my mom came to pick me up, I told her the story, wishing I had been able to tell him how much I appreciated this outlier donation.

My parents took me to Longhorn that night so I could get what is still one of my all-time favorite meals: a loaded baked potato. I used to literally live on just baked potatoes. 

While enjoying my conduit for sour cream, bacon, and cheese, I looked up and realized that, at the table next to us, was the guy who had given me the ten dollar bill. This was the guy I hadn’t been able to properly thank. My mom was concerned that it would look like we were using his money to go out to dinner, but I was adamant about going up to talk to him, and she eventually relented and allowed me. 

I rode over to his table and reminded him who I was, and how grateful I was for the biggest donation I had received in all of my hours sitting outside of Walgreens. He was very humble about it, but then his wife started telling me that she worked for the Palm Beach Post, and she thought she might be able to get my story into the paper. I told her that would be great, and she took down my information.

While I thought the lady was very nice, I didn’t have high hopes for the publicity. I didn’t know what she did at the paper, and even at 12 years old, I had already figured out that those kinds of promises rarely came to fruition. I kept chugging along outside Walgreens, and checks from the mailing list kept dripping in. At this point, we were hoping that we could get close enough that my parents could bridge the gap. But it still wasn’t looking too great. And my dad was repairing my current chair almost every night, keeping it going so I could make it through the school day. 

But then, sure enough, we got a call from the Palm Beach Post. They wanted to do a story on my attempt at fundraising for a new wheelchair. They came out, took pictures, and put it to print. The headline read something like: “All boy with cerebral palsy wants for Christmas is an electric blue power wheelchair”. 

The story hit a nerve with people, and the donations started rolling in. We were pretty excited. It was going to be close, but it seemed like we might hit our goal. But then everything changed when we received an anonymous donation, who absolutely refused to identify herself (we just knew she was an elderly lady), for $5,000. I couldn’t believe it. My parents couldn’t believe it. Not only did we have enough for the chair, but we were able to set some aside for future repairs and maintenance. It was unbelievable.

There was no way we could have known when we started this what the path towards success would look like. We just started trying. And that’s usually how these things go. In the words of Conor McGregor, “God loves a trier.” There was definitely some luck that happened here, but luck is what happens when you are doing everything you can to get something done. There have been many times in my life when I have started on a path, not knowing how I could make it successful, or what good could come of it. And just like this, things happen. This is the rationale behind going to every industry conference I’ve ever attended. I never know why I’m going specifically, but I do know that making the effort to go allows for unexpected, spontaneous things to occur. You just need to take the initial steps and do everything in your power. And then use the results of that work to pull yourself up to the next level.

The other lesson here is to allow people the opportunity to step up and be generous. Create the opportunity for generosity. People want to help. Let them. It is a win for everybody involved.

(Wasn’t that touching? Your mom thought so. Speaking of me touching your mom, maybe be like her and get me to text you every Sunday by sending a text to the number 484848 with the word CRIP in the message. Also, share this with somebody who needs to take the first step, even if the rest of the plan isn’t clear.)

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Crippled CEO Blog #069: Solving Impossible Problems

Crippled CEO Blog #069 (hehe):

“When you see a good move, look for a better one.” – Emanuel Lasker, World Chess Champion from 1894-1921

Y’all know that I play chess. I have a 90 minute lesson with my coach, International Master Vitaly Neimer in about two hours. 

There is an unexpected benefit to playing chess. It’s also a benefit you get from playing video games. It is also a benefit I get from having cerebral palsy and being in a wheelchair.

It’s problem-solving. But not what you’re thinking.

It seems pretty obvious that practicing chess improves your problem-solving skills, and it does. That’s not the surprising part.

The piece that I have picked up from chess, and also from video games, and also just living my life as a cripple isn’t just an enhanced ability to solve problem, but perhaps more importantly, the understanding that problems which at first seem absolutely impossible, if worked on long enough, if tried again and again, if toiled over even when they seem hopeless, can eventually have a solution. It’s the idea that impossible problems aren’t impossible. Because being good at solving problems is awesome, but you won’t even bother trying if you don’t think there’s a chance. Doing these exercises that teach you, by example, that tough problems start out looking unsolvable gives you the motivation necessary to find the answer and not just give up. 

Like I said, I have started out with a healthy dose of this just by being lucky enough to be born with CP. At this level of disability, everything is a problem solving exercise, most of which initially seem impossible, and almost all of them are entirely unique to me. When all of your parts work like everybody else’s, someone else who moves like you can show you how to ride a bike or type on a keyboard. Nobody else is quite like me, so I’ve had to come up with my own ways of doing literally everything, from using a pen to typing to eating to using the bathroom.  Once you do this enough times, you start to assume solutions exist in every area of your life, and every area of your business. You find ways to upgrade your pool fence with options that weren’t supposed to be possible. You break the number one rule of mixing business with friends and family by ONLY working with friends and family. You have a record-breaking year during a global pandemic.

It is important to get better at solving problems, but it is even more important to train yourself to know that impossible problems can be solved. If you weren’t fortunate enough to be born with cerebral palsy, I recommend games. Chess is great. Video games are great. Puzzles are awesome. Do low stakes tasks that initially seem totally impossible. And then do them anyways. Doing the impossible takes practice, but it is a good skill to have.

(Why don’t you just share this with somebody? Do it for me. Also, guarantee you get next week’s post by sending a text message to 484848 with the word CRIP in the message. Your mom will be proud. She told me last night.)

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Join the fam and make sure you never miss a post. Send a text with the word CRIP to 484848. I'll send you the link each week to the newest blog as soon as it's released.

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