The worst thing about being an entrepreneur and no one talks

Being an entrepreneur is not always as glamorous as the media portrays it to be. There are difficult situations and times and no one talks about them.

I crouched down, hiding myself and Esmeralda (my dog) behind a bush as the two tall figures and a vaguely familiar face advanced. It couldn’t be…

I quickly searched LinkedIn on my phone, staring at the unmistakable face of the approaching woman. It was her and, even worse, the man she had mentioned. At this point, in this position, I only had one option: I headed towards my hiding place while a dog – which was not mine – distracted the couple long enough for me to sneak behind the alley without being detected.

Victory on points. Yes, that’s the life of a CEO. Confused? Don’t worry; I’ll explain exactly why hiding in alleys can become one of the not-so-glamorous, but necessary (and strategic) aspects of life as an entrepreneur and CEO.

I never wanted to be the “face” of a company for many reasons, one of which was that I didn’t want to put myself under the added pressure of having to be “present” or “professional” at all times. Unfortunately, while hiding in that alley, I learned firsthand that it doesn’t matter if you are the public “face” of the company; If you’re the CEO, you have to be conscious of your presentation to the world at all times, and it sucks.

If you’re a model or celebrity, it’s only natural that the way you dress or present yourself in public is fodder for the paparazzi and the tabloid press, so you have to be very careful when you go out.

I, however, wasn’t exactly at my best when I was walking my dog ​​in my own neighborhood wearing Forever 21 kids’ sweatpants (they’re comfy and run big!), a giant hoodie from my fiancé, a messy bun, and socks. It’s not like I was showing up at an investor meeting or a press conference; I was on my own block…

In this case, the woman was someone I had associated with a few years ago (when we lived several counties away), and her husband is very well connected in the local business community.

When you’re the CEO and responsible for representing your company in deals and negotiations, the last thing you want is for an impromptu and unprofessional meeting with an important person to jeopardize a pending or future opportunity.

Believe me: I never imagined hiding in alleys when I imagined the “CEO life,” but when I looked at the options, it seemed like the most logical thing to do:

  1. Let them see me, but pretend I didn’t know them, which could turn against me or be awkward if one of them recognized me.
  2. Letting myself be seen and introduced – in a less than ideal state – to her husband, and making a first impression that would likely discredit his professional perception of me through word of mouth and online praise, and possibly jeopardize future deals.
  3. Hide in the alley and avoid everything.

If you ever see a dog walker in socks hiding in an alley, it may be a CEO saving face, avoiding a very unforeseen encounter, and maintaining his professional reputation in the best way possible.

Before social media existed, people were much less concerned about their personal opinions being leaked to the public or their reputation being decimated online. A few years later, it seems almost a requirement or even an advantage for entrepreneurs, founders, and CEOs to build up a large digital presence and make their views known to the public.

The problem is that doing so – especially as a CEO – presents some very real and potentially irreversible risks.

In today’s age of unforgiving cancel culture, it seems like the safest thing to do as a CEO is to keep your lips sealed and your raw, honest, potentially unpopular or controversial opinions to yourself — and that can feel incredibly stifling.

I don’t know any founder or CEO who enjoys having to censor themselves 24/7 and is too shy to have a social media presence.

Have you ever had a down week, month, or quarter and wanted to vent or share your innermost insecurities about the future and longevity of your company with a friendly, listening ear? If so, you can put it back where it came from, because as the leader of your company, your behavior sets the tone to some extent, both internally and externally.

Smile all day? Maybe…

Since part of your entrepreneurial job is to maintain team morale and the positive perception of your startup by the public, it is not very beneficial to air your company’s dirty laundry or your deepest, darkest concerns, which could undermine your team’s and the public’s trust in your company. Therefore, you may need to keep your true feelings to yourself, lock away your fears, and put on a smile to imply that things have “never been better,” since saying otherwise will only have a negative domino effect.

Doing the above will provoke a huge dose of cognitive dissonance in any brutally honest person, making them feel disingenuous and manipulative, but at the same time may seem like the most responsible option available.

The caveat here would be for CEOs of publicly traded companies who are required to make recorded earnings calls to investors, in which case the curtain is drawn and the skeletons are revealed. Running a private company, on the other hand, leaves it up to you what you do and what you don’t reveal, for better or worse…

A common trait that I have observed in every entrepreneur in my circle – myself included – is the insatiable desire to explore, explore, and launch new ventures. In other words, I don’t know many entrepreneurs who are 100 percent satisfied with staying in one lane, working on a company or tackling a problem forever.

Unfortunately, that entrepreneurial spirit that led us to create a company is precisely what can lead us astray in the eyes of the public.

While it shouldn’t necessarily be a conflict for a founder to spend their free time exploring a new industry, problem, or company, doing so—even if only as a “fun side hustle”—can raise red flags about a CEO’s dedication to their core company.

Simply put, any outside activity can raise the question of why the founder is not devoting all of his time, energy, and resources to the core business, even if he remains fully dedicated but in an age of delegation and diversification.

So if you’re a multi-passionate, insatiably curious entrepreneur (like most of us), you may feel pressured to keep your other activities on the back burner to avoid negative reactions that could hurt your main business or your professional reputation.

As an entrepreneurial founder and CEO of a company, one of the hardest truths to face is that at some point, the “B” word (Burnout) may appear, leaving you with the surprising and unsettling feeling that it may never go away. .

If you’re burnt out from a sport, hobby, or even a job, you might choose to take a break, take a sabbatical, or even change your activity. When it’s your company that’s causing you to feel burned out, the options are a little bleaker. You might

  • Hold on and hope it goes away
  • Start looking for a replacement or successor and assume a more passive role.
  • Start looking for exit options (selling the company, selling a part, closing and liquidating, although these have serious and far-reaching implications).

Considering that it can take years for your business to go from a fledgling seed of an idea to a legitimate, profitable, and growing operation, it’s also important to consider how your dedication may wane in that time. You may get tired of the sector, the struggle, the uncertainty or simply your company in general. Unfortunately, in your role as CEO, your burnout can affect many more people than you think.

There is a perplexing question that will stump you and probably 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 will never know exactly where “there” is, and even if you catch a glimpse of “there,” you will not be sure that you will ever stay “there.”


Businesses fluctuate, trends and seasonality flow, and industries evolve. Therefore, you will have to struggle with the constant uncertainty of wondering if the path you are taking is still the best use of your time and resources, both now and in the long-term future ahead of you.

If you’re lucky enough to build a comfortable, automated, cash-rich business, you can become complacent and believe you’ve arrived at the panacea of ​​“there,” only to be blindsided by a sharp, unexplained drop in revenue. Or you can spend years making what seems like minimal progress, wondering every day if it’s time to quit, or if you just need a little more patience and persistence because “there” is lurking just around the corner.

As CEO, it is up to you to make that decision, and unfortunately you may never know which was the right decision: to persevere or to give up…

In recent years, the job of “entrepreneur” has been more than glorified by the media and, from the outside, it would be easy to assume that the option of “being your own boss”, working from anywhere and doing whatever you want in exchange for unlimited economic benefit, it is a dream come true.

To some extent, some aspects can be a dream come true, when things are going well. However, in addition to the lesser-known drawbacks, there are more obvious ones that deserve reiteration:

They say it’s lonely at the top, but it’s also lonely at the bottom, which is exactly where you might feel like you belong when you’re in the early stages of building a company and isolated from the positive press, partnerships and perks that encourage other founders to keep going.

Speaking of benefits, we must not forget that each decision you make can make your company grow or fail, or at least greatly influence the path it has left.

I’ve made 5- and 6-figure decisions that have been involved in risk, and sometimes they’ve resulted in exceptional performance, other times a big goose egg, and me scrambling to fill the hole. Risk and uncertainty may decrease or subside from time to time, but they never completely disappear.

And while we’re talking about risk and money, we might as well talk about the embarrassing things we do to save a dollar. No CEO wants to admit that he spends forty hours of his week on tedious tasks that might atrophy a brain from boredom, but are less expensive than paying another team to do tasks that you could do yourself.

When you’re an early-stage entrepreneur, struggling to get started or cash-strapped, or simply in a slow season for your business, you’re likely to take any job to stop the bleeding, no matter how tedious, unstimulating, or unglamorous.

I clarify that I am not trying to imply that business owners or CEOs deserve pity or want you to feel bad for them.

Being an entrepreneur is a choice, and a difficult choice to make day after day. However, I want to remind you that if you are an entrepreneur feeling despondent in the trenches, wondering if it should be easier, more fun, more glamorous or safer, pay attention; many of us are in the same boat, right there with you, even if we can’t show it publicly.