5 Questions I Wish I Asked Myself Before Quitting My 6-Figure Job

And the one consideration 99% of “wantrepreneurs” get wrong when exiting the rat race.

When my manager called me into his office for an exit interview, he asked a question that at the time felt comically condescending: “Is there anything we could have done to keep you here?”

As his glassy blue eyes met mine, paternal empathy and genuine concern seeped out from below his furrowed brow. I searched his face for a tick, a smirk, or any other tell of his insincerity. Nothing. Maybe this was the Oscar-worthy performance that reeled him in an endless supply of 8-figure clients and 7-figure commissions.

Unfortunately, no amount of method acting could erase the truth I knew all too well. That truth? This manager — and probably most colleagues from my M&A group — were not going to miss me one bit. In fact, they were probably glad I was leaving. One less person to take part in the bonus pool, right?

I made the fatal flaw that no employee should ever make on my way out: I let my waning engagement show, and my performance all but screamed “I’m mentally 9 toes out the door…”

Luckily, I still left with three prestigious back-to-back finance jobs on my resume and a 6-figure savings account that was supposed to be my entrepreneurial safety net and all the startup capital I’d ever need. Unfortunately, I failed to ask myself 5 questions that would have changed my quitting timeline drastically. If I could go back, yes, I would do things very differently. I urge you to heed my warnings and ask yourself these questions before making an irreversible career decision yourself.

1. Will this unexpected wildcard throw a wrench in my plan?

Quitting a stable job to become a full-time entrepreneur is rarely a unilateral decision made by one person alone. Many aspiring digital nomads, future freelancers, and entrepreneurial hopefuls consult their friends, family, significant others, and career mentors before making the leap. However, sometimes the very people who offered you support and consolation end up being the wild cards that hurl a wrench in your plan when least expected.

I had been living with my now-fiancé (then boyfriend) for three years before I quit my job. He’d seen me wake up at 7 am and return home at 2 am, when I accidentally woke him as I crawled into bed after an 18-hour “shift”. He’d watched me panic on weekend trips when my Blackberry’s red flashing light would summon me to some time-sensitive non-emergency and ruin the plans we’d solidified weeks prior. He listened to me cry at 6 am when my office’s industrial printer broke and I needed his help lugging 70 pounds worth of pitch decks to a director’s house before his 8 am flight.

In other words, my fiancé was nearly in the trenches with me. The negative toll of investment banking impacted his life as well — for years. Thus, he was understandably supportive of the idea of a career change that would improve my, his, and our lives together.

Fast forward three years later, and the tables turned completely. He was the one in the demanding desk job, while I was the one with the career autonomy and scheduling freedom, pursuing multiple ventures and embarking on new enticing opportunities left and right. And yes, he got jealous.

He started to get that entrepreneurial itch he’d never had before. Unfortunately, the genius of our plan was a balancing of risk between a stable, 9 to 5 partner and a riskier entrepreneurial one (me). My partner quitting his high-paying accounting job had never been a part of the plan. Instead, it threw a big, compromising wrench into everything I’d been working towards. All of a sudden, my entrepreneurial journey — though three years in — started to look a whole lot riskier.

• In-progress acquisitions for new ventures I’d been eyeing? Not anymore.
• Attempting to have kids in the next two years? Don’t think so.
• Possibly buying a house in our gorgeous but overpriced neck of coastal Southern California? Ha. Ha. Jokes.

While this was the wildcard we never expected, I couldn’t really fault him. Why was it that I got to follow my risky entrepreneurial dreams and he didn’t? He’d put the years and tears into a trying career as well, had built up a nest egg of savings, and wanted to spread his wings outside of his cubicle. Who was I to tell him no?

These are the unexpected factors you shouldn’t shy away from when contemplating the decision to quit a full-time job for an entrepreneurial unknown. A family member might agree to step in as your safety net if needed, but their plans can change, too.

Ask yourself: Is my success predicated on another person’s artificially (or temporarily) limited risk? If so, play out the unexpected: What happens if that “safety net” or “support system” is no longer so safe or supportive?

2. What’s the difference between going all-in today versus 6 months from now?

I know a guy who left his job to run a mask-selling business online at the height of the pandemic. He did well for himself — to the tune of $1.5M in 12 months. Not too shabby. Today, he’s selling his business for just $250k — less than 50% of the profit he made last year. With the prevalence of vaccines and the mask-optional guidelines, it’s no surprise that he’s anticipating declining sales in the coming months and years, hence the lower purchase price.

Nonetheless, he took a leap on a potentially once-in-a-lifetime opportunity when he quit his full-time gig to pursue mask selling at just the right time, and it paid off. If he waited another 6 months? He probably would have missed his window and the bulk of his profits.

That said, most of us probably aren’t pursuing businesses or freelance opportunities that have a finite expiration date. In fact, most astute entrepreneurs seek out just the opposite: They strive to find an opportunity with significant longevity to ensure they aren’t quitting a stable career for a 12-month risky gig.

When you assess the opportunity that’s tempting you to quit your job ASAP, is it actually something that requires your round-the-clock involvement today? What would happen if you started it part-time, on nights or weekends, until it gained enough steam to seep into your 9 to 5? Would that six months of moonlighting sabotage the opportunity entirely, or are you just antsy to break free of your corporate chains and thus, allowing excitement and emotion to needlessly accelerate your timeline?

3. Will this particular endeavor increase or decrease my IMV and my FMV?

A few months back, I coined the term “IMV” or “Intellectual Market Value”. I proposed the idea that an entrepreneur is only as valuable as the knowledge, experiences, and unique niche-specific expertise gained through their startup journey. The less you stretch yourself to learn, grow, and overcome difficult challenges or master an underrepresented niche, the less value you possess.

Hence the danger of total delegation: If you’re the least valuable person in your venture, you may be in for a rude awakening…

Conversely, the greater your IMV, the greater of a transferrable, lucrative, and respected role you may play in future jobs, consulting gigs, partnerships, or entrepreneurial ventures.

In addition to considering whether your IMV will increase as you pursue the new venture, I believe it’s also important to assess how your FMV will fluctuate, assuming “FMV” stands for “Future Market Value”.

Are you honing a skill that will be of continued or greater value in the future? Or, alternatively, are you leaving a career that will quickly outpace you and prevent you from ever jumping back into the corporate grind as a last resort backup plan? If leaving your career today means saying goodbye to that industry forever, you’ll want to be sure you’re amassing a new valuable skill set so you aren’t left in the dust if things don’t pan out as you hope.

4. What’s the pivot plan or exit strategy?

When you pursue a new venture, the outcome is usually unknown. However, it’s reasonable to assume it can go one of three ways:

• Very good (you’re seeing monthly payments that exceed yearly salaries)
• Okay (self-sustaining and profitable, but no one’s buying an island)
• Very bad (ramen noodles are starting to sound like a gourmet luxury)

When we think of a venture doing exceptionally well, it’s no surprise for an owner to cash out with an IPO (go public) or sell the company to an investor, new operator, or strategic acquirer (M&A). However, selling your company isn’t always a sign of success — and it also doesn’t need to be the exit strategy reserved for startups that reach 8- and 9-figure valuations. Believe it or not, selling the venture you’ve created just may be a solid exit strategy for a “failed” or lackluster business endeavor, as well.

If you’ve done everything you can to attempt to grow your new venture, and you realize you’re lacking a critical factor required for success — be it funding, expertise, connections, or anything else — selling to a better-equipped owner may be the best option. Sites like Bizbuysell and Flippa allow you to sell even pre-revenue companies to eager, motivated future owners. “One man’s trash is another man’s treasure” rings very true in entrepreneurship — take it from someone who’s been sifting through thousands of failed startups, seeking a gem in the rough to acquire and turn around.

That said, if you aren’t quite ready to part with your fledgling venture, there is another option: a pivot plan. A pivot simply means a tweak that might prove your business more valuable under adjusted circumstances. I suggest testing out a few potential tweaks before throwing in the towel or calling up a restructuring broker:

• Tweak your audience: If your offer is solid but your audience is nonreceptive, perhaps you chose the wrong client avatar. Tweaking it doesn’t cost you a dime, but it could make a world of difference.

Case in point: I have a business that couldn’t reach a profit despite 5-figure ad spend. We tweaked the audience, cut the marketing costs, and reached profitability within a month. My only regret? That we didn’t do it sooner.

• Tweak your price point: Sometimes, your price is too high, but sometimes it’s too low. It’s possible your price is either out of sync with your audience’s budget or simply outside their expectations. Pricing your product or services too low can raise even more red flags than pricing them too high.

Case in point: A few years ago, my company tested out a brand-new offer at an introductory price. The offer included all the bells and whistles, but the price was to the floor. When we surveyed our audience in post-purchase market research, they let us know the ridiculously low price set off “scam” alarms in their heads. Two years later, and we sell that same product with far fewer bells and whistles for three times the price.

• Tweak your product: If you’ve already gone through the trouble of tweaking your marketing, A/B testing to the max, targeting different customer groups, and exploring various pricing options, your product or service may be the common denominator in need of tweaking. And that’s okay!

Case in point: When I launched my last company, we had a nationwide, seasonal plan to deliver and market our product. Unfortunately, after about 6 months of lackluster results, we decided to scrap the rigid plan we thought our audience wanted and do something completely different. We changed our product, our delivery, our timeline, and our marketing — and it worked, to the tune of multiple 6-figures within the year.

Now, it’s your turn to preemptively ask yourself: If things go downhill, what is the plan?

5. Is this actually what’s been suppressing my progress and success? (what 99% fail to consider)

There’s a common fallacy that invades the minds of employed wantrepreneurs who daydream of quitting for greener, more lucrative self-employed pastures. This fallacy is simply the idea that their job, alone, is the culprit for the stagnation of their entrepreneurial goals.

Thus, 99% of those aspiring future entrepreneurs, freelancers, and self-employed creatives fail to consider one very key possibility: What if their job wasn’t a hindrance to those goals after all, but rather a scapegoat of an excuse to delay, defer, and push the risk a few more weeks or months down the road?

Think of it this way: If you couldn’t build your venture into an early-stage proof-of-concept (at the least) when you had the stability and financial security of a full-time job with benefits, what makes you think you’ll suddenly be better-suited to do so successfully on your own once you do cut that cord?

While leaving the nest or burning the ships might seem like the perfect strategy to ignite a person’s fight or flight response and scare them into successful entrepreneurship, it doesn’t always turn out that way. Fight and flight aren’t really the only options; there are two others we often forget: Freeze and fail.

Some newly unemployed wantrepreneurs will buckle under the weight of continued bills, costly healthcare, and a limited amount of runway before their dwindling savings can no longer cover their future rent. Success isn’t the only outcome in response to self-inflicted unemployment.

Additionally, failure is a very real possibility too — and it doesn’t mean you weren’t prepared. Businesses fluctuate with seasonality, market changes, worldwide upsets* (*cough: pandemic), and industry disruption. Even the best-laid plans can’t guarantee a perpetually profitable venture, and in the early stages of your new endeavor, there’s no need to invoke the additional pressure of relinquishing your stable paycheck one moment too early.

The one caveat that changes everything

While I’d like to tell you the above 5 questions can guarantee your perfect timing as you leave the corporate grind to embark on full-time entrepreneurship, I’d be remiss to ignore one critical caveat.

Based on the above 5 questions, I left too early.

• My “safety net” changed his mind
• I didn’t foresee a time-sensitive market change in the next 6 months
• I delegated everything in my first venture and let my value wane
• My pivot plan and exit strategy were entirely nonexistent
• I believed once released from the corporate golden handcuffs, I’d sprout my wings and morph into some magical Zuckerberg-esque business genius

If you’ve read this far, you’d assume I messed up big-time, leaving way too early. However, here’s the one caveat that made my decision that much easier: Staying felt riskier than leaving.

The entire leveraged finance group in my office had been laid off a month or so prior, and in my few years working in finance, the attrition was high. I saw firings left and right — from Ivy League graduates who rubbed a VP the wrong way to 20-year managing director veterans who simply couldn’t pull their 7+ figure weight in a down year.

My job felt anything but secure, and I lived in constant fear of the day I got fired. Thus, I didn’t see leaving as the biggest career risk to consider. Instead, I saw staying as rolling the dice on whether I’d ever leave that firm on my own terms or theirs. In other words, quitting when I did was a preemptive move on my strategic timeline. And no, I don’t regret it.

That said, if I’d had a cushy, stable, secure job — even one paying half of what I made in finance — I probably would have stayed quite a bit longer while side-hustling my way to entrepreneurship. Truth be told, I might not have quit a job like that to this day — despite my insatiable passion for building, running, and growing multiple endeavors. There’s something about the unparalleled peace of mind a predictable, biweekly paycheck, 401k match, and health insurance bring that early-stage entrepreneurship simply can’t buy — and yes, I would hold onto those as long as I could.