5 Signs You’re Doing Something Very Wrong In Your Business

No, entrepreneurship isn’t supposed to be like this.

You don’t have to be breaking the law to be doing something incredibly wrong as an entrepreneur, and I’m not just talking about ethics and morals. I’m referring to the day-to-day indications that you’re kind of running a creaky, leaky, unstable ship that just might be headed for impending disaster. If you’d like to steer yourself back to fairer waters — or at least towards a fate slightly less tragic than the Titanic’s — these are five signs to look out for and nip in the bud like…yesterday.

And no, it doesn’t matter if you’re profitable or growing. I’ve grown a profitable ship to a massive degree, only to look reality in the face and swallow the harsh truth that in order to course-correct, I’d have to tear down years of progress. Don’t do as I did, do as I wish I did; as you know, hindsight’s 20/20, but you just may be early enough to save your ship.

1. The need to sneak around

I’m not talking about running away from the Feds or evading arrest (though those would be pretty good indicators you’re probably not running things above board and white hat). However, I’m specifically referring to those founders and startups tiptoeing furtively just below the gaze of the vendor or partner they fear. If you feel you have to skirt around nuanced guidelines and regulations to avoid rocking a boat that could permanently knock you out of entrepreneurial orbit, that’s a good indication your venture’s time running as is just may be limited.

Want examples? No problem, I’ve got plenty:

• Not-so-ad-friendly niches relying on ads for leads or sales
• Direct outbound marketing (physical mail, cold email, or cold calls) in a regulation-tightening industry
• Legally controversial products or services using conservative and guideline-increasing payment systems, banks, and platforms

Do you know what it’s like to see a high-volume business’s lucrative sales come to a screeching halt overnight, for no apparent fault of your own (the founder) or anyone on your team? I’ve both seen it (multiple times) and experienced it personally, and I can tell you it ain’t pretty. I can also tell you it rarely happens without warning whatsoever.

If you’ve gotten any indications that you may be treading on thin ice with any of your key vendors or partners, attempting to fly under the radar so they don’t remember you exist and thus allow your existence a bit longer, you’re playing a dangerous game (with a finite end).

Maybe your bank deems your industry, product, or service “unsavory” or otherwise too legally controversial to warrant the risk of your business. I’ve seen banks turn away businesses, freeze accounts, and leave founders high and dry with no sympathy nor opportunities for reinstatement or amendment. Likewise, I’ve seen entire businesses built on certain advertising platforms or social media channels go “poof” thanks to an unannounced guideline change.

I’ve seen and witnessed tightening regulations on certain marketing methods that are responsible for multi-billion-dollar revenue (yes, billion with a “B”), and I’ve watched the wisest founders start pivoting and plotting their escape plans and alternate solutions, while others dropped like flies.

Simply put, if any of the above rings true or feels familiar, I’m here to share some news that shouldn’t be so shocking: You don’t have to live — or operate your business — this way. In fact, you shouldn’t unless you want to perpetually remain in fear of a fate you can’t control, sometimes exacted by a vendor, partner, or platform to which you pay oodles of money.

If your business resembles any of the above, I’d argue it isn’t built on a firm foundation, and the time to pivot or problem-solve to a new solution (or vendor, platform, or partner) is now. Entrepreneurship doesn’t have to mean living in fear, especially not of the vendors whose rent you’re paying.

2. Relief at the losses

At the beginning of your business, it might be normal to “fear” success. For example, you may be shocked or afraid that you won’t be able to live up to your first customers’ hopes and expectations. However, that’s the rational newbie fear that propels you to overdeliver for those early users. A very different story can be told if you feel fear — or anger or annoyance — at incoming sales months or years (or decades) into your business. What’s even more telling is if you start to feel relief at the losses, whether that’s a customer cancelation, a prospect falling through, or a record-low sales month.

Does the idea of “relief at the losses” sound impossible or irrational to you? If so, great, but know that there really are some entrepreneurs out there who are secretly, silently celebrating their ventures’ lulls and losses — and it isn’t because they’re masochistic founders eager to watch a good failure drama or sabotage all they’ve built. There’s typically a much more rational, telling reason behind their seemingly irrational, unexpected reaction.

Founders who feel a tempting tinge of potential relief at the idea of shutting things down, selling them off, or disappearing and doing something else altogether — even the “dreaded” 9 to 5 so many fantasize escaping — may have grown weary of, burnt out from, and unenamored with their venture.

The truth here is that not every business is forever, and not every founder is meant to forever lead a business, even if that business is healthy enough to carry on. Sometimes it’s worth taking a step back and honestly assessing if you’ve lost that fire, and if perhaps someone else would be better suited to carry the torch and keep your startup’s light burning.

You aren’t a perpetual slave to your startup, and you’re allowed to hand over the reins, sell the whole kit and kaboodle, and explore your next new adventure. What you probably shouldn’t do, however, is allow your secret burnout and desire for change to seep in and poison a thriving startup that still has a beating heart and opportunity for growth.

3. Denying the bomb

You know what I’m talking about: When someone — or an industry or consumer behavior change — is coming to eat your lunch or take lunch off consumers’ menus altogether, it’s rarely a complete surprise. Nonetheless, so many founders hang on, denying, ignoring, or cowering below the fear of that inevitable ticking time bomb. Bluntly put, if you’re clenching your eyes shut to avoid the writing on the wall, you already know you’re just prolonging a game destined to fail.

That’s not to say your business is headed for sure extinction, but it is to say that the answer here is to innovate, reposition yourself, or target a new market (or industry) with your solution and expertise, rather than cling to a dying, aging one and praying for just one more day.

4. The temptation to cheat

No, I’m not referring to the temptation to cheat your customers out of their purchased products or Uncle Sam out of his “fair” share. I’m referring to the temptation to cheat on your business with another venture or opportunity that you’re stuffing in the back of your mind, while secretly resenting your own business. Sometimes the temptation to cheat isn’t so bold as a new career interest, but instead shows up in your own desire to take a less-than-respectable path. Are you reaching for the shortcuts? Are you shirking the obstacles that most strongly need addressing?

If you succumb to even a glimmer of the temptation to turn to “black hat”, shortcut, or not-100%-ethical choices because they feel like the faster, easier solution, you’ve already mentally checked out of where CEOs should sit. The best course of action requires an objective step back and a reassessment of why you’re seeking those shortcuts and acting as if your current role, venture, and reputation are worth risking. Perhaps it’s because you feel stuck, either at a certain revenue plateau or at a less-than-inspiring time in your entrepreneurial journey.

Remember: Your startup isn’t holding you hostage and tying your hands to the steering wheel. If you feel like it is, that may be the sign that your prime reign has run its course and a change in leadership and pursuits might be just what the doctor ordered for both you and your current venture. If your startup isn’t lighting you up, and is, in fact, bringing out the worst in you (and thus, you’re bringing the worst to it), those signs shouldn’t be ignored.

5. Awaiting the sign

Speaking of signs, I hope you aren’t sitting there wasting your time waiting for one. I hate to break it to you, but the sign to tell you “where to go next” with your venture just may be the one staring you in the mirror. Too many founders fall prey to fictional timelines that we believe “should” govern our journeys:

• Raise funding this month
• Reach profitability in that month
• Grow to this size by the end of year one
• 10x by year three
• Field incoming acquisition bids by year four or five the latest
• Sail into the sunset of an exit or ringing the bell at the NYSE, as our five-year victory is complete

Spoiler alert: Very few startups — even successful ones — follow the aforementioned journey to a “t”. In fact, few follow it at all, to an “x”, “y”, or “z”.

If you allow entrepreneurial platitudes, headlines, and random timelines relayed to you in business-building textbooks or case studies to guide your next step or provide the arbitrary “sign” you’ve been missing, you might find yourself waiting a long, long time for a savior that never comes.

There is no rule about how long of a period of stagnation is due to seasonality, a bad economy, or a sign of ultimate decline. Likewise, slowing growth, a bored team, a shrinking or shriveling (or dying) target market could all be temporary blips or fate-defining factors that hint at the end.

The vision for what your next 1, 3, and 5 years should be isn’t necessarily printed on a cookie-cutter map; instead, it’s up to you to decide, and you won’t always know if you’ve made the right decision until you’ve played the chosen card. Many startup lulls, pitfalls, and challenges are surmountable, but that doesn’t mean pushing forward will result in the end goal you had in mind. Some obstacles aren’t worth overcoming, and it takes deep introspection, honesty, and humility to admit that to yourself (and your team). Still, I’d rather be in control of my five-year plan than slay dragons just to survive another day closer to somewhere I may not want to go.

The sign you’re doing something right

While the entrepreneurial journey can be wrought with tough decisions and ongoing uncertainty regarding whether you’ve made the right one, there is one sign that’s never failed me in any career decision. This may be hard to come by, but if you can find the decision that results in a combination of both pride and peace, that just may be the path worth exploring.

When I say “pride”, I’m referring to the pride you feel from making the choice you deem best, no matter how hard or uncomfortable. With respect to “peace”, this is one of those hard-to-convey feelings that will reinforce that yes, no matter how unimpressive, unexpected, or even sometimes embarrassing a decision may be (and I’ve made all three), it was ultimately the right one for you.

You’re the one who has to walk your path, run your business (or choose not to), and live with the long-term effects of the decisions you make, so you certainly shouldn’t be an afterthought at any step along the way.