Life

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 Feeling

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.

Mini-Epilogue

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…