A different form of meditation – For a day or two, I didn’t think about much. Frankly I couldn’t As Jesse said before the start, for a period of time, this was our job. No kids, no taxes, no work. I wasn’t concerned with much of anything other than what was in front of me. For me, meditation is about focusing on the breath and getting out of my head. But it’s also about just taking a break from all the things that can consume me day-to-day.
Just how much separation I got – It wasn’t until I dug back into my phone that I realized how much I’d separated from everything else. Just how little I’d thought about work. About social media. About some of the personal things I won’t share here but that keep me up at nights. I never expected to stop thinking about these things, and it wasn’t until I realized I’d taken a break that I realized they were out of mind. To be clear, areas of stress aren’t inherently bad. It’s just nice to take a break.
It’s harder at the top. Nearer the goal. – It’s easy to associate being better at something as making things easier. Or that when a business grows, it’s easier. Well, if the mountain reminded of something, it’s that you may be closer to the top, but it’s likely that headwinds are going to be blowing in your face. And so when you’re most tired, you have to dig even deeper.
Forced focus at night because you just can’t see much – We hiked at night with headlamps. Other than the light from the moon and lights at the aid station, the course was dark. That meant we had to focus on the steps immediately in front of us. And as much as we could look up a bit ahead of us, we couldn’t see the rest of what lay in front. And sometimes that’s a good thing. Knowing the goal is important but sometimes just how big it is can be more than daunting. It can be debilitating. It can be overwhelming. Rather than just focusing on the next step and you can take what’s coming as it comes.
“Mastery” comes thru repetition – Let’s be clear. I didn’t master the mountain. But I’ve been asked about the monotony of the climb. Having to do the same climb 13 times. But this climb was hugely reflective of how you get better at a skill, and certainly to master it. Learning something requires doing it over and over again. This is a valuable skill. Especially when each repetition was nothing remotely close to easy.
Repetitive doesn’t mean redundant nor identical – Each climb was similar and yet different. Of course it was the same basic route, but whether in the day or at night. Sunrise or sunset. It was always a bit different. The heat would change, the wind would change. The trail was worn in different places. Or perhaps I chose a slightly different route (even 3 feet to the left might feel very different). And then there are the mind games. Parts you thought were easier are harder on lap #11. And harder parts get manageable. But each climb brought a different challenge. So yes, it was repetitive. But in no way was each lap identical to one prior.
Get used to never feeling “normal” – anyone who’s done an endurance event knows one of the biggest balancing acts is the one with your stomach. Heat, altitude, emotions, adrenaline, big efforts. All of them change the biology and chemistry in your body as never before. And depending on what you’re able to get in, that affects fatigue and certainly is a cycle affecting your stomach. Getting sick on lap #6 helped me feel better. But that didn’t mean I felt good. Just better. And even at night, when I was able to get down more calories, I never felt like my stomach was settled. A day later and I was still feeling it. You can’t wait to feel good or normal. Sometimes that uneasy (in this case nauseous feeling at times) was just going to stay and you had to navigate thru it.
Hiccups suck – there’s no lesson here. Only my desire to say that I got them for 18 hours on and off. Never experienced that before. There’s no medical explanation. But suffice to say that my go-to solution is normally to hold my breath or turn my head upside down. Neither of which was an option on the mountain. Hiccups suck. Hopefully you don’t get them that often. And hopefully you don’t get them in the middle of a climb…
Sharing experiences adds such richness to them – I was only one of a few that had someone I knew at the event and who wasn’t participating nor event staff. Sarah was an unreal trooper. For someone who generally needs more sleep than the average person, the fact that she hung thru and was an absolute ball of energy until 630am when I finished was just awesome. Many others were solo. Most everyone made friends, whether in the FB group previously, on the mountain, at aid stations, or in the recovery area. For my part, having my wife see me race for the first time in our 10 year relationship, riding down the gondola with me each of my last 9 laps, taking video of me, cheering me on as I headed out, and most of all, being there with a smile and words of encouragement at the top each time. Well, let’s just say I’m getting teary-eyed as I type this. It’s something that has been forever added to our shared memory bank.
The lows will come. But they will also go – Not feeling “normal” is one thing. Feeling really down, tired and drained is another. When Sarah arrived, it was the worse I’ve felt at an event in ages. It sucks feeling this way. But you learn that some lows aren’t actually as low as you end up going. But most of the time, you get better. You just have to stay in the game and keep plodding along one step at a time if necessary.
Taking a break, even near the end, can be a good idea – With 2 laps to go I took a 15-minute nap. I could have decided to push thru. 2 laps out of 13 seems really late in the game to take a nap. But those 2 laps were another 4 hours. 2 out of 13 doesn’t seem like much. 4 hours does. Keeping some perspective about what’s left in the game, and when to recharge, can make the last part more manageable. It also meant I was semi-lucid when I finished. Which is a good thing…
It’s okay to compete when many others aren’t. And it’s to not care about competing no matter who else is – I trained for this event. Multiple weekend mornings, I was out early to do sets of stairs or to get biking on the road. For hours. That’s time away from my family. Time away from plenty of other things. And so I wanted to see what I was capable of. So yes, I paid attention to my times and wanted to see what I could do. That doesn’t mean I didn’t stop to say hi or to give words of encouragement to others. I also know that plenty of others out there weren’t competing. That’s cool. We all had our reasons and our own goals. It’s just important to know what those are going in.
Why I didn’t sleep – this one is a bit multi-faceted:
Like I said, I trained for this. My goal wasn’t just to finish. I didn’t disrespect the event, but I felt confident I could finish. But that wasn’t all it was for me. I could’ve slept more than I did and still finished. (Note, I say this very respectfully since some people finished at the cut-off. Some didn’t reach their goal, whether 13 summits or something shorter. I’ve been that person as well.) In this case, I wanted to see what all those hours of training, of countless sets of stairs, of hours on the bike, those hours away from my kids, the tradeoffs of skipping dessert (sometimes) – what those allowed me to do. Those were the prep. I wanted to see the outcome. Sometimes you know you can do something, but it’s crucial to do it.
The experience of going thru the nite is surreal. It’s so hard to explain. Whether as a participant, spectator, or crew. Sunrise. Thru the heat of the day. Sunset. Moonrise. Moonset. Dusk. Just an amazing life experience to do an event thru literally a full day cycle.
Doing what others aren’t. I like doing things others don’t. Or won’t. This event is one of those things. Even within the event, there are layers to that. And even though this is more of an event than a race, there was an important point I wanted to get across. To myself and in the story I knew I would tell. Sometimes you get outworked. Sometimes you consider something differently than others do. At this event I was one of those guys. Others were ahead of me at 10pm. But they no longer were at 3am. They had their goals. That’s fine. This isn’t about judgment or being “better” than someone else. It’s about remembering and knowing that sometimes you just have to sleep less than others. And sometimes, and this is the part that sucks, when you’re sleeping, someone else may be still climbing the mountain. In whatever context that fits. I think it’s important to remember both sides of this point. And to be intentional about which side you want to be on. Because there’s a place for both. You just have to be aware of it.
I wanted Sarah to see what I’m made of. Again, in 10 years of being together, she’s never seen me race. Racing had been a big part of my life. Tri’s, ultra-distance cycling, whatever. This has been an important part of my life. And I’ve been totally at peace not doing so since we’ve been together – building a life and family take plenty of work, none of which do I ever think twice about. But she got to see me doing an endurance event. And pushing like I did was something I wanted her to see in me.
Final point – Playing against my weakness. With this type of event, it’s hard to say things play to your strengths. So this was more about playing against my weakness. If that makes sense. I suffered in part because of the heat and altitude. When the sun finally set, my body started coming back to me. I had to take advantage of the cooler temps to get the miles in. Because of my sweat rate and stomach issues, it would’ve been a different level of suffering to be out there in the afternoon of day 2. So I had to play against that. Plus, 4 years each at MIT and investment banking, even though years ago, prepped me for all-nighters. Knowing that I would truly suffer and suck during the day, I had to stay out during the night. So sometimes, you have to know where you’re going to suck. And do whatever you can to avoid that…
One of the most miserable nights and then days of my life.
From a performance perspective, I didn’t have anything to worry about – I’ve always prided myself on overdelivering in whatever role I’ve been in. And I consistently got the highest ratings possible, max bonus number each year, and was promoted multiple times during my time at the company.
I was an 8-year employee and Senior Vice President in a billion-dollar company, and I just had this nagging feeling like I was going to be let go.
In general, I’m not a paranoid person. Sure, we all have our insecurities. And I have my version of Imposter Syndrome, but no one close to me would really ever describe me as a paranoid individual.
So why did I have such a strong feeling, what did I do during that crazy day, and where did it lead me?
The reality was that I was starting to think about doing my own thing. I had started a magazine a long time ago, a failed entrepreneurial venture, but it whet my appetite for doing my own thing.
Not to mention that over the past few years, an increasing number of my friends were entrepreneurs, I was reading more and more about people’s stories of going on their own, and I happened to be married to a woman who believes in entrepreneurship and whose dad owns several businesses.
It was getting close to “put up or shut up” time.
And then I became a father and our world changed (for the better). But now I was not only thinking about what I wanted for myself and my wife, but the legacy and lessons I wanted to leave and teach my son.
I had begun having conversations about what I might do next. Within my industry, I was fairly discreet and in fact told nobody internally what I was contemplating. The people I spoke to I generally trusted, but you never know how word might spread and who is friends with whom.
Once you start having these thoughts and conversations, as anyone who has been there can attest, they start to dominate your thoughts. But more than that, I started to feel like I was living a double life. I had my at-work persona and conversations, and then there were those that I had outside of work. Not to mention it takes an enormous of thought and stress to keep track of what you have told to whom.
Oh yea, and then wife was pregnant with our second son.
That’s some of the backdrop.
So yes, I was in an particular mindset and certainly under a bit of stress.
Again, I’m not a paranoid person by nature, but it just felt like the other senior executives around me were behaving weirdly. Very short conversations, limited eye contact in the halls, what almost felt like avoidance.
Having let go more than a few folks in my professional lifetime, I felt like I was seeing the behaviors that I had displayed towards those who I knew were on their last days at the company.
Why that one night in particular was the one where I was convinced I was being let go the next day (that’s a nicer way of saying “fired”)– I don’t have a great answer.
But my wife will be the first to remember the conversation we had where I told her I thought I was being fired the next day. And the reality is there is no way that feeling is going to do anything but suck. Regardless of what I had been contemplating (leaving) and where I thought I was headed (out on my own). One always wants to be in control, to be able to know that you were the one who made the choice, not someone else.
So yea, that night kinda sucked.
The Day Of
Years ago, I played blackjack with a team in Vegas – yes, the same type of stuff as in the movie “21” or the book “Bringing Down the House.”
I’ll never forget that feeling of walking thru a casino, heading to the tables, knowing that I wasn’t simply just walking thru the casino for kicks. I was there for business. And I knew that I had team members waiting for me. (To be clear, everything we did was legal. Against house rules, yes, but there is a huge difference between against house rules and against the law. One gets you kicked out of a casino. The other can get you arrested. We were always very clear about doing things legally.)
As a member of the team, we were up to something and others didn’t know about it. Unless you’ve been there or been in an analogous situation, it’s hard to explain. But there’s this sense of feeling like you know more or are in on something that most everyone else isn’t.
That emotion is the best way to describe how I came into the office that day. Except I wasn’t trying to win money at the blackjack tables. I was convinced I was no longer going to have a job by day’s end.
On my way up from the parking, I stopped by a colleague’s office to tell her that today was likely my last day. Not by my choice.
Not unexpectedly, she didn’t believe it, but soon realized that I was serious, and ultimately, if I in fact did know it was coming, it was just a matter of wait-and-see.
Near my office, the awkward behaviors continued, at least by those that were around. It was odd that a good number of folks weren’t around. Had other senior execs been told to keep their distance? (Now this is starting to sound like paranoia, I’ll admit…)
Over the course of the day, I had several conversations with my wife, my colleague, and one of my best friends. All were supportive. And most importantly, all were caring and compassionate. If you indeed are going to be fired and “know” it’s coming, the least your friends can do is be compassionate. It’s never a pleasant thing.
Lunchtime came and went. I have no recollection of whether I ate lunch.
And then all of a sudden, I lost access to one of the company systems. To this day, it must have been a weird glitch, but it did happen and I could not login to a tool I used all day every day. But again, having done a number of terms (our short-hand for “terminations”), I knew that concurrent with pulling someone in to a departure conversation, the IT department began their process of removing access to pretty much everything company related. It’s standard practice and honestly is a good risk management tool.
5 minutes went by.
Then 10 minutes had passed.
A painfully long 30 minutes later, and I was still sitting in my office and no one had stopped by or entered.
So I called my good friend who told me enough is enough. She told me that rather than continue to wait in misery, to go do the proactive thing. But in a way that wasn’t explicit.
It turned out that we were beginning performance reviews and setting objectives for the coming year. So my friend suggested that I go to my boss, the company president, to ask if there was anything he felt I had been lacking in during the prior year. In particular, the question was framed in the context of wanting to build my current year’s objectives as appropriately as possible.
In so doing I was partly forcing his hand. At the least, I was trying to get any information, any indication of whether my sense of gloom for the day had any merit. (Call it my version of charging the torpedo like they did in “The Hunt for Red October.” How’s that for pushing analogies?…)
I got a pretty plain-vanilla answer, but it erred on the side of the fence of “you’ve been doing a great job” much more than “er, ah, um, why are you asking, and can we talk about this later.” Nothing of that sort.
It did help me feel better. And at least made me feel better that I was taking some action, as opposed to sitting around, waiting for someone else to take theirs. Because as bad as being let go is, the sitting and waiting is truly miserable. (When we let go a bunch of people the year prior, my teams were the last ones to be notified – I knew that it sucked for everyone, but let’s just say I have more empathy for them than I did before.)
And I also felt that if my boss couldn’t address the issue on the spot, well, at least I had done my part. And was proud for taking that step.
As you might have already figured out, I wasn’t let go that day. Nor the following day or week.
But it truly was a miserable day. And I still don’t know if something I did on that day changed people’s minds (quite unlikely) or why I completely misread several people’s behaviors. I never did address it with the folks I thought were acting strange.
I felt what I felt. Was certain of it. And of how I thought the day would end for me.
Needless to say, it was one of the situations where I was clearly happy to be wrong.
What I learned and What I Did With That Learning
No matter who you are, there is always someone to answer to. For many people, it’s their boss. But even for entrepreneurs who have no “boss”, whether they are answering to customers, investors, or their spouses (!), it is not like they have zero accountability. And should those folks be displeased, the entrepreneur may not be fired (unless the investors of course have that ability), but they can lose their business (or go out of business) if they fail to address customer issues.
Talk to any business owner who has previously had a job, and they will all say that it’s just different. Yes, you will always answer to somebody. But being your own boss and answering to your customers is fundamentally different than answering to your boss. It’s a different level of control that you have being your own boss. And in fact, being in much more direct control of their future is a common theme for why many people become/became entrepreneurs.
The same with me.
I realized I hated the idea that things like my bonus were ultimately someone else’s decision. At least a someone else who was titled “my boss.” I hated the fear I felt that someone else could fire me. And then frankly, I hated that I couldn’t impact my future, my financial status, and my freedom, to the degree and in a way that I wanted.
And so that was a big part of what I learned from that horrid day.
Looking back, it was also clear that it was just time for me to move on. There are a host of things that built to that point, meaning that I could have seen scenarios where I stayed in this role and was truly happy. But all those little things, both personally and professionally, that came together in my life changed how I looked at what I wanted (and needed).
It was the proverbial nail in the coffin for my future at the company. I had been leaning towards going out on my own anyways, but this did it for me. There was definitely no turning back. No way that I wanted to nor even that I could turn back. I had taken the red pill and could no longer see things the way they had been.
And yet, I didn’t walk out the door the next week either. I have a mortgage, a wife, and at the time, our second son was on his way as I mentioned earlier. And while I had some money saved, it would have been irresponsible on so many levels to walk out or even to give 30 days’ notice that next week.
While there was urgency, there was no rush to make a move. If that makes sense.
And even my “risk-tolerant” entrepreneur friends would all say the same thing. (By the way, the idea that entrepreneurs are pure risk-takers and don’t consider risk is foolish. Truly something they don’t get credit for. Managing risk is very different than being oblivious to it and being foolhardy.)
Making the decision to go out on one’s own does not mean one has to leave a job immediately. It means, and in particular what it meant for me, was that I needed to ensure that I was taking steps to be out on my own.
The conversations started ramping up. More thought and research occurred.
Most importantly, each day and each week I took an honest assessment of the prior period to make sure I could answer the question, “Am I steps closer to moving on?” Sure, there were days and weeks where that wasn’t the case. There were moments where I felt like I was moving backwards. And then there were times where I thought I was making progress and was getting closer to a move only to have it fall apart for one reason or another.
Ultimately, I left to start something with a few folks I knew. I felt great about the team and the opportunity we had discussed. I felt good about my financial situation – enough that it wouldn’t be a massive point of stress for a period of time. (Having been in massive financial stress during my prior venture, I knew just how detrimental it was to my ability to execute, not to mention to my mental, physical and emotional well-being.) And I had the support of those around me.
This isn’t to say that I’ll never work for someone ever again. I think that’s a silly statement to make. Whether that prevents me from being a “true” entrepreneur is something I’ll tolerate. We each have our levels and boundaries. And frankly, we can never foresee all the life events that can happen.
At the same time, this isn’t some judgment against people who work for others or some “call to arms” for people to leave their jobs. I think that would be pretty arrogant to believe that my values, choices and decisions are the best ones for others. But these needs are much more than urges for me. They are driven from within and have to be addressed. And even served.
Whether or not they sustain the rest of my life is a question I don’t consider. For now, this is what I need to do.
And this here is about my experience and my choices. And I was excited to make my way on this new venture and certainly felt good about my decision.
Not surprisingly, the story doesn’t end there, nor did things progress the way I thought they might.
Within 10 days of my last day, our founding team had been reduced from 4 to 3 founders. 2 months later, my 2 remaining business partners told me they wanted out.
Literally within moments of hearing this news – which I wasn’t expecting but also wasn’t surprised to hear, if that makes sense – my head moved on to considering what’s next. (Not sure that now re-qualifies me to be a “true” entrepreneur…)
After an already-planned family vacation to stay with some friends in the Hamptons, I decided to see if I could get some consulting clients. Honestly, having done consulting before, I was not that excited by this prospect, but a good friend spent an hour on the phone with me and convinced me to give it a strong push. That the value I could provide was significant. That the income I could generate would be attractive. (By the way, you usually don’t get the latter without doing the former.) And that I could have the life and lifestyle that I wanted at this time.
And so I began putting my name out there. After a month, I read the book “The 10X Rule” by Grant Cardone, and I realized I need to up my game a good amount. I had gotten a couple clients on board, but knew I wasn’t pushing as hard as I could.
Which gets us and me to today. I’ve got 6 clients, with several more in advanced conversations.
I’ve said no to a number of folks where I didn’t feel like there was a great fit, usually where I didn’t feel like I could add significant value and pretty quick ROI. I’ve said no to consideration for a full-time opportunity. Which interestingly enough, and certainly not planned so by me, has turned into a consulting project.
I’m doing work I really love. Yes, I answer to my clients, but I’m my own boss. I work most of the week from my house and am in a formal office a couple days per week. I get to see my wife and kids multiple times per day typically. I’m pleased – actually surprised – with where my business has gotten to both by client count and income after 10 weeks of pushing, I am certainly not done and am continuing to push hard on growth. But I’ve learned to acknowledge the wins as they come.
And while any (or all) of my clients could turn around tomorrow and say they don’t want to work with me anymore, a) I doubt that’s going to happen; and b) I know that even if they did, I’ve lived through the day where I thought I was getting fired from my only source of income and that I’l be okay.
Honestly, I would’ve been fine. I would’ve bounced back (kinda have no choice when you have responsibilities). Maybe how I responded when my partners told me they wanted out is my proof of that.
But I also feel like, as much as control is this myth people dream about, I am able to affect my future in a way that I have much more influence on than when I was in this most recent job.
Now, when I go to bed, while I do somewhat dread our 6-month old waking us up in the middle of the night, the reality is that I am ending each day exhausted but proud of what I’ve been a part of that day. Which has been doing my best to provide massive value to my clients. But more importantly, I’m spending time with my family, which is really what this whole thing is about for me.
And then before my head hits the pillow, there is this excitement and almost giddiness of what I can help create the next day.
Which sure beats freaking out about getting my ass fired…