And why I hid in an alley when a business partner walked by.
I crouched down, concealing myself and Esmeralda (my dog) behind a bush as the two tall figures and a vaguely familiar face marched forward. It couldn’t be…
I quickly pulled up LinkedIn on my phone, staring right into the unmistakable face of the woman approaching. It was her — and worse, the man she’d mentioned. At this point, in this position, I had only one option: I made a beeline for my hideaway while a dog — not mine — distracted the couple just long enough for me to duck behind the alleyway undetected.
Victory — and a close call. Yes, that’s the life of a CEO. Confused? Not to worry; I’ll explain exactly why hiding in alleyways can become one of the not-so-glamorous, yet necessary (and strategic) aspects of life as an entrepreneur and CEO.
I’ve been fairly strategic to keep myself (my likeness) at arms’ length of the businesses I’ve run; I never wanted to be the “face” of a business for many reasons, one of which is that I didn’t want to invite the added pressure of having to be “on” or “professional” at all times. Unfortunately, while hiding in that alley, I learned firsthand that it doesn’t matter if you’re the public “face” of the company; if you’re the CEO, you do have to be mindful of your presentation in the world at all times — and it kind of sucks.
If you’re a model or a celebrity, it makes sense that how you dress or present in public could be fodder for the paparazzi and tabloids, so you’re on your A-game when out and about. I, however, wasn’t exactly on my A-game when walking my dog in my own neighborhood in fluffy kids Forever 21 sweatpants (they’re comfy and run big!), my fiancé’s giant hoodie, a messy bun, and crocks with socks. It’s not like I showed up to an investor meeting or a press conference like that; I was right around my own block…
In this case, the familiar-faced woman was someone I’d struck up a partnership with a few years ago (when we’d lived counties apart), and her husband is very well-connected in the local business community.
When you’re the CEO and the one responsible for representing your company in deals and negotiations, the last thing you want is for an impromptu and unprofessional run-in with an important person to compromise a pending or prospective future opportunity. Trust me — I didn’t ever foresee myself hiding in alleyways when I envisioned the “life of a CEO”, but when I played out the options, it made the most sense:
- Get spotted but pretend I don’t know them, which could come back to bite me or get awkward if either of them recognizes me.
- Get spotted and introduce myself — in my far-from-ideal state — to her husband, and make a first impression that would likely discredit the professional perception he’s had of me through word-of-mouth and online accolades and possibly compromise future deals.
- Hide in the alley and avoid the whole thing.
If you ever see a crocks-with-socks-wearing dog walker hiding in an alley, it just may be a CEO saving face, avoiding a very unplanned encounter, and maintaining their professional reputation the best way possible.
Back before social media was around, people were far less worried about their personal opinions getting leaked to the public or their reputation decimated online. Fast forward a few years, and it almost seems like a requirement or even an advantage for businesspeople, founders, and CEOs to amass a large digital presence and make their viewpoints known to the public. The problem here is that doing so — particularly as a CEO — presents some very real and potentially irreversible risks.
In today’s unforgiving cancel culture era, it seems the safest move as a CEO is to keep your lips zipped and your raw, honest, potentially unpopular or controversial opinions to yourself — and that can feel incredibly stifling. I don’t know a single founder or CEO who enjoys having to over-censor themselves 24/7 and be too gun shy to have a social media presence, yet there are many of us out there.
Have you ever had a down week, month, or quarter and wanted to vent about it or share your innermost insecurities about the future and longevity of your company with a kind, listening ear? If so, you can shove that right back where it came from because as the leader of your business, your demeanor to some extent sets the tone — both internally and externally.
Does that mean all smiles all day long? Maybe…
Since part of your job is maintaining team morale and keeping up the public’s positive perception of your company, there isn’t a great benefit to airing out your company’s dirty laundry or your deepest, darkest concerns that could shatter your team’s and the public’s confidence in your business. Thus, you may have to suck up how you really feel, keep your fears under lock and key, and brave a smile to imply things have “never been better”, since indicating the opposite will only have a negative ripple effect.
Doing the above will give any brutally honest person a whopping dose of cognitive dissonance that feels insincere and manipulative, but it can simultaneously feel like the most responsible option available.
The caveat here would be for CEOs of public companies who are required to give recorded earnings calls to investors, in which case the curtain is pulled back and the skeletons revealed. Running a private company, conversely, puts what you do and don’t reveal in your court — for better or worse…
One commonality I’ve observed among entrepreneurs in my circle — myself included — is the insatiable itch to explore, probe, and pursue new ventures. In other words, I don’t know many entrepreneurs who are 100% satisfied staying in just one lane, working on one company or tackling one problem forever. Sadly, that entrepreneurial spirit that led us to start a business is the very thing that can lead us astray in the public’s eyes.
While it shouldn’t necessarily pose any conflict for a founder to spend their free time exploring a new industry, problem, or venture, doing so — even just as a “fun side hustle” — can send up red flags regarding the CEO’s dedication to their main company.
Simply put, any outside pursuits can pose the question of why that founder isn’t dedicating all that time, energy, and resources to the main business, even if they’re still fully dedicated, but in a season of delegation and diversification. Thus, if you’re a multi-passionate, insatiably curious entrepreneur (like most of us), you may feel pressured to keep your other pursuits on the down-low to avoid backlash that could harm your main company or professional reputation.
As the founder and CEO of a business, one of the hardest truths to confront is that at some point the B-word (burnout) may creep in, leaving you with the startling and unsettling realization that it may never go away.
If you get burnt out of a sport, hobby, or even job, you can opt to pause, take a week off — or a sabbatical — or even change lanes altogether. When it’s your company that’s instigating those feelings of burnout, the options are a bit bleaker. You could:
- Suck it up and hope it will pass
- Start looking for your replacement or successor and take on a more passive role
- Begin to pursue your exit options (sell the company, sell a portion, shut things down and liquidate — though that one comes with serious and far-reaching implications)
Point being, with the understanding that it can take years to get your company from a fledgling seed of an idea to legitimate cash-flowing and growing operation, it’s also important to consider how your dedication may wane in that time. You may tire of the industry, the struggle, the uncertainty, or just your company in general. Unfortunately, in your role as CEO, your burnout may affect far more people than you’d anticipate.
There’s one vexing question that will perplex you to no end, which will likely make you question your path on a daily, weekly, or monthly basis. That question: Are we there yet?
The problem with the “Are we there yet?” dilemma is that you’ll never know exactly where “there” is, and even if you do reach a glimmer of “there”, you won’t be assured that you’ll get to stay “there”. Why? Businesses fluctuate, trends and seasonality ebb and flow, and industries evolve. Therefore, you’ll have to wrestle with the constant uncertainty of wondering if the path you’re taking is still the best use of your time and resources both now and in the long-term future ahead.
If you’re fortunate enough to build a business into a cushy, largely automated, high cash-flowing place, you may get complacent believing you’ve reached the panacea of “there”, only to be blindsided by an abrupt and unexplainable dip in revenue. Alternatively, you may spend years making what feels like minimal progress, wondering every day if it’s time to call it quits, or if you just need one more iota of patience and persistence, as “there” lurks right around the corner.
As the CEO, it’s up to you to make that call, and sadly you may never know which was the right decision: To persevere or pack it in…
In recent years, the job of an “entrepreneur” has been more than glorified by the media, and from the outside looking in, it’d be easy to assume the option to “be your own boss”, work from anywhere, and do as you please for unlimited financial upside is a dream come true. To some degree, aspects of it can be a dream come true — when things are going well. However, in addition to the above lesser-known downsides are the more obvious ones that still deserve reiterating:
They say it’s lonely at the top, but it’s also lonely at the bottom, which is exactly where you may feel you belong when you’re in the early stages of building a business and isolated from the positive press, partnerships, and profit that encourage other founders to trudge forward.
Speaking of profit, let’s not forget that your every decision may make or break your company — or at least heavily impact its remaining runway. I’ve made multi-5 and 6-figure decisions that have been mired in risk, and sometimes they’ve resulted in an outstanding return, other times a great big goose egg and me scrambling to fill the hole. The risk and uncertainty may lessen or subside from time to time, but they never fully go away.
While we’re on the topic of risk and money, we might as well also throw in the shameful things we’ll do to save a buck. No CEO wants to admit they spend forty hours of their week on grunt work that could drive a brain to atrophy from boredom, yet it’s less expensive than paying another team to do tasks you could do yourself. When you’re an early-stage, bootstrapped or otherwise cash-constrained entrepreneur — or simply in a down season of your business, you may take on any and every job to stop the burn rate bleed, no matter how tedious, uninspiring, or unglamorous.
To clarify, I don’t mean to insinuate that entrepreneurs or CEOs deserve pity or want you to feel bad for them. This job is a choice, and a hard one to make day in and day out. I do, however, mean to remind you that if you’re an entrepreneur feeling beaten down in the trenches, wondering if it’s supposed to be easier, more fun, more glamorous, or more certain, take heed; many of us are in the same boat, right there with you, even if we can’t publicly portray it.
