5 Stages of Entrepreneurship That Can Wreak Havoc on Your Mental Health

From an entrepreneur who flushed her 6-figure savings and prestigious career down the drain at 24.

The scariest day of my professional life took place in a high-rise cubicle, with political riots burning down the city and bankers rushing home to take cover in their luxury condos. Despite the commotion all around me and the footage of flames, vandalism, and violent attacks right outside our building, the sent email in front of me was far more frightening. Within a split second, I was overcome with petrifying anxiety, paralyzed in my chair, too afraid to leave, yet equally afraid to stay.

That email was nearly three years in the making, yet it felt jarringly abrupt and catastrophically risky, as if I’d chosen to give up a coveted role with a 6-figure salary at a prestigious Wall Street firm on a whim. A strange thing happens when you blindside your manager with a “Two Weeks Notice” subject line in the middle of a political upheaval that has your firm on lockdown: Nothing.

Finally, he responded with something along the lines of: “Noted.” That was all. At that moment, the gravity of my decision came crashing down, and I feared I was entering deep, dark waters far more perilous than I’d imagined.

Spoiler Alert: It gets worse before it gets better. A lot worse. That day was merely the beginning of the downward spiral that was a first-time founder’s entrepreneurial journey. Before you step out on the ledge to embark on a similar journey, you may want to brace yourself for these five stages of entrepreneurship and the havoc they may wreak on your mental health.

1. These notifications will taunt you for months, if not years

Within weeks of embracing my newfound self-employed (let’s be real: unemployed) freedom, a flood of notifications started bombarding my inbox. The faces of former colleagues who remained chained to their desks by the golden handcuffs of a coveted Wall Street title started popping up with “Congrats” notifications, shoving their promotions unmistakeably front-and-center before my jealous eyes. There was no escaping their vertical corporate ascension, while my marketability plateaued as I sat in my lead and asbestos-plagued studio, attempting to make something out of nothing.

The first stage of entrepreneurship is regretful comparison. In these first few weeks, months, and sometimes even years, you’ll be taunted by the incessant reminders of the career you gave up. You’ll start to question whether your old job was really that bad.

You’ll block out the memory of the 6 am panic-fest as you rushed to deliver your director a last-minute request while he assaulted your competence through threatening emails and voicemails, causing your panic levels and cortisol to rise at an exponential rate. Sure, that job may have come with an elevated heart rate and medically diagnosed anxiety asthma, but maybe that 6-figure salary and 5-figure bonus precluded your right to complain…

In that early, desperate, money-strapped stage in your entrepreneurial career, you fail to see the intangible value of happiness and fulfillment. Money and titles aren’t everything, though we always want what we can’t have. And just like the laws of supply and demand, the more that stable, attractive salary and fancy, respectable title seem scarce assets just out of your reach, the greater value you arbitrarily assign to them.

2. Your concept of time will change drastically

When you work a salaried job with finite hours or a standard workweek, your concept of time is governed by the same clock that rules the rest of the world. That clock and calendar tell you to punch in on mornings, punch out at night, and hustle until Friday, when the reward of the weekend is no longer a hypothetical prize, dangled like a carrot in the distant future.

Once you dive into the world of entrepreneurship and self-employment, those constructs of time vanish entirely. Instead of counting down the days until Friday, you count down the days until “success”, a far more vague mythical destination that you may never pinpoint with any certainty.

Instead of counting workweeks, you’ll count down in phases:

1. Intangible progress: Before you make a dime, you plan and draft and pound the pavement. You’ll constantly question how long is too long to see the financial return? When should traction catch on?
2. Dwindling savings: Once you give up on counting down the intangibles — or perhaps you simply catch a frightening glimpse of your remaining savings — you pull out the calculator. It’s time to crunch some numbers and get real about your remaining runway. As you divide your dwindling savings by your monthly spending, you realize you’re down to a few final months before a job is no longer optional. Panic mode sets in big time.
3. Measurable results: Finally, with the concrete fear of your diminishing runway hanging a flashing timer over your head, you start getting serious about progress tracking. You create milestones for everything, and you start measuring your time in those goal-focused results.

As you sink deeper into the world of entrepreneurship, it’s easy to disconnect from the concept of time that governs employed society. However, a healthy (or unhealthy) dose of financial fear will accelerate your countdown and drive you to hustle harder, faster, and perhaps a bit more brazenly. When you arrive at stage three and start measuring time on tangible results, the days, weeks, and months start to bleed together, as your world spins at an alarming rate.

3. This question will haunt you with every dime you spend

It took me two full years to realize that one fatal flaw (and my personal dealbreaker) ruled all three of my businesses. That flaw was costing me between $5k and $8k per month, bleeding me dry with a sorry return to show for it. However, at the time, I was far too scared and timid to rock the boat.

It took another year for me to realize how much I dreaded one frustrating aspect of B2C sales. It wasn’t until I was up to my eyeballs in thousands of prospect inquiries and hundreds of customer support requests that I realized perhaps this wasn’t the dream business I’d always hoped for…

Whether you’re in the early stages of your first venture or five years in and running multiple companies, you may take stock of the life and businesses you’ve created. That moment might reveal that you’ve married yourself to a handful of ventures, tasks, or responsibilities that you truly can’t stand. If those businesses are total cash cows, you might be able to put up with a little annoyance here and there. However, if they’re barely paying your bills or worse, it may be time to make a drastic change.

The question “Is this the right business?” will burrow its way into your brain and haunt you with each dime you spend and each loss you take.

Some first-time entrepreneurs know themselves and the market well enough to land on the perfect-fit business the first time around. Most don’t. If you’re like the rest of us who have to endure years of downs, ups, more downs, and a whole lot of trial and error before determining our entrepreneurial sweet spot, don’t be afraid to give this question some real consideration. Knowing that your current business isn’t your forever dream job is a comforting step towards finding the future venture that is.

4. You’ll be plagued by this impossible decision, which will only exacerbate your confusion

The greatest misconception about entrepreneurship is that success is finite, binary, or easily identifiable. The problem with “success” is that it’s subjective. For some, success is profitability. For others, it’s 7 figures. For others, it isn’t financial at all, but rather touching a certain number of lives or meaningfully contributing to the world. With all these subjective barometers of success, it becomes incredibly difficult to determine at which point to call your venture a success or a failure.

You may consider things like:

• How much spending is too much spending in the aim for success?
• How much wasted, unemployed, salary-less time is too much?
• How much minor success do I need to feel confident the long-term success is still on its way?

Until or unless you hit it big or achieve an objective milestone deemed unequivocal “success”, you’ll likely be plagued by the difficult decision of when to call it quits versus promising. This conundrum will be further confused by the ebbs and flows of business, even long after you reach profitability or national renown. When you see your revenue drop from $60k/month to $6k/month (and your expenses hover closer to $10k/month), how long do you give yourself to potentially recover before pulling the plug and walking away?

This is one of the most vexing (and emotional) decisions with which you’ll wrestle, and the unfortunate truth is without a 100% accurate crystal ball, you’ll never know if your decision was the right one until it’s far too late.

5. Then, these thoughts will creep in and hit you like a ton of bricks

Back when I was 25, fresh off the toxic corporate grind of investment banking (and elated to exchange my 6-figure salary for comparative freedom), I knew exactly what I wanted out of my career. I’ll be honest: My standards were low.

All I desperately wanted was to build a business that could provide me the financial, time, and location freedom to work from the comfort of my home, without an abusive boss breathing down my neck. I remember thinking I’d do anything if I could just make $40k from that horrid, dilapidated studio apartment.

Then, things changed. As my businesses grew and evolved, so did the goal. As our revenue ticked up, my standards increased (along with my confidence), and my risk tolerance shifted. I started to give myself back the permission to dream about the loftier goals I’d wanted:

• Business was important, but it wasn’t everything to me anymore.
• My dogter entered my life and helped me reprioritize my heavily skewed money and success-obsessed mindset.
• I fell into new passions, new opportunities, and new higher-ROI activities.
• My partner assured me my identity was comprised of more than that first startup.

That brings me to today, when I’ve recently started to reassess my life and question my priorities. Once you put your entrepreneurial goals in perspective, you may start to question the goal that spawned this journey in the first place.

• Why did you choose this entrepreneurial path?
• Was it all worth it?
• What was the goal, anyway? Has that goal changed? Will it change?
• How much of a sacrifice is too much?
• Could this goal have been achieved through better, faster, safer means?
• Do you even want that outcome anymore?

While asking yourself this onslaught of questions may seem like throwing an unwelcome monkeywrench in your pre-planned path, it’s important to realize that just as businesses evolve, so do we. There’s nothing wrong with changing your mind or your goals, and there is no one right way to do entrepreneurship.

The psychological roller coaster doesn’t end

From the day you consider pursuing an entrepreneurial venture to the day you stop (if ever), the psychological roller coaster of building, running, and growing businesses doesn’t end. I’ve cried to my fiance when my first startup was losing thousands per month, and I’ve also arrived at similar hysterics when my later company’s 5-figure months were slashed to 4, without an iota of warning.

Entrepreneurship will not coddle you, comfort you, or give you an “A” for effort. Entrepreneurship is uncertain, trying, and not for the faint of heart or mind. However, for those seeking an exhilarating challenge and forced fast-paced self-improvement, entrepreneurship is the best experience out there.

Whether you sell a 7-figure business or fold a cashless company, entrepreneurship makes you a better, more resilient, more resourceful person with far more tools to excel in any future venture, business, or other pursuit. Yes, it’s a constant psychological roller coaster of relentless, unforgiving ups and downs; and yes, it’s worth it.