5 Things You Need to Delete to Acquire Startup Success (Even if You’ve Already Been Successful)

Success really is rented, not bought, and earned every day

There’s a six-word phrase I’ve probably repeated more than any other statement in my life, to which I often receive knee-jerk pushback. I’m sure I’ve likely uttered this phrase at the very beginning of my career, in the “lost” times in between ventures and failures, as would be expected. Ironically, however, I know I’ve stated this phrase on a weekly basis even at the height of my entrepreneurial and financial “success”, when I was first making more in a month than most people make in a year.

The phrase: “I just want to be successful.”

The instant (biased and expected) feedback from my closest friends and family was “You already are!”. While we all have different definitions of success, I certainly hadn’t (and arguably still haven’t) reached mine, or else I wouldn’t be so voraciously seeking something more — or something else.

Before you click away assuming I’m going to get all preachy and spiritual, telling you that the real definition of success has nothing to do with careers, business, or income, have no fear; I would never. Instead, I’m going to double down on why my feelings of underachievement were so valid — and why you may not be on the path to perpetual success at all.

This morning, I was listening to a podcast hosted by one of my neighbors (who also happens to be a mid-9-figure-net-worth CEO, best-selling author, and TV personality). The gem of knowledge didn’t actually come from him, but rather from the guest interviewee, who nearly stumped the host (and me) with an underrated statement that couldn’t ring truer.

He said: Despite having global acclaim, selling hundreds of millions of widgets (this guest is an impressive person in his own right), even he has found that success is rented, not bought, and needs to be re-earned every day.

This is the truth no one admits: Success isn’t a place you get to and ease up on the gas; in order to continually achieve (and maintain) it, you have to continually learn, grow, and humble yourself in new pursuits. That said, there are a few toxic ingredients we need to kick to get there in the first place, so here are five poisonous traits standing in the way of your success.

Ego

It’s easy to say we don’t value our self-worth based on our net worth, but actions can tell a different story. Have you ever stayed in a job or prolonged a business venture for the money alone? I know I have. It wasn’t always because I actually needed that money to pay the bills or stack my pile of riches. Instead, it was partly — largely — because that money was one of the few tangible, irrefutable validators that I had built something of note.

My subconscious attachment to that number — and the desperation to cling to it at all costs, even at the detriment of my other long-term goals — reveals that my ego had become tied up in those income sources.

If I didn’t run XYZ company, where would I get my respect?
Without this many $$,$$$,$$$ beside my name, who would take me seriously?
If I backed off the gas, changed paths, or pursued anything less impressive, wouldn’t it fundamentally undermine everything I’d worked to build?

Those are the questions I wrestled with every time I swapped one pursuit for another, one seemingly booming opportunity for a risky or unproven one, and every time I tried to stray from “good” in pursuit of great.

Unfortunately, I’m not alone here. These are the decisions you’ll likely wrestle with if you decide to buck the ego-affirming safer bet in pursuit of the wildcard that’s calling you. If you can’t delete your ego and accept that taking a temporary hit now (financially or otherwise) might be the key step to reallocate resources towards a more rewarding goal, you may never achieve that next level of success.

Fear

Do you know the “hot stove” analogy? It goes like this: The kid puts his hand on a burning stove, predictably gets burnt, and thus learns never to do that again (thanks to the painful and fear-inducing consequence). Here’s the problem with entrepreneurship: Long-term entrepreneurial success — and successive success across multiple diverse ventures — requires putting your hands on many hot stoves, getting burnt countless times, and returning fearlessly enough to one day find the switch to turn the stove off.

You can’t just get burnt once and avoid stoves forever; startups don’t work like that, despite the natural human inclination to allow fear to guide and protect us. However, the fear of getting burnt, failure, and clawing our way back to ground zero isn’t the only fear we need to delete for startup success.

Another fear few founders are willing to fess up to, though many of us inherently possess, is the fear of learning new things, from fetus-mode. By “fetus-mode”, I simply mean that accomplished founders who’ve come from prior successes often have a hard time humbling themselves to the point of newbie status. Sadly, that’s the type of humility required to fully embrace (and master) new technologies, industries, and opportunities, and it’s the number one reason some successful people play it a little too safe, stay in their lane, and one day get eaten by the next big thing on the block.

Luckily, this fear goes hand-in-hand with killing off that ego, so once you’ve disconnected your sense of self from your former accolades and achievements, it’s far easier to humble yourself before a new pursuit.

Shame

There have been a few times in my earlier entrepreneurial life when I would cringe at the prospect of sales. While my inexperience as a salesperson was perhaps partly to blame, this instinctual cringeworthiness was a crucial indicator of something far more telling: I was ashamed of what I was selling.

I believe one of the key indicators of whether a person will be successful in sales and entrepreneurship surrounds their shame — or inversely, passion and pride — around the widget (or project or industry) at hand. It is unspeakably difficult to successfully market, peddle, and represent a product or company around which you feel shame.

On the contrary, when you feel authentically passionate and proud to represent, peddle, and market a product or service, sales feels easy, almost natural, and even rejection doesn’t dampen that organic enthusiasm.

The moral of the story here is simple: If you have shame around what you’re learning, doing, or selling, you may want to reexamine whether this uphill battle is worth pursuing. If you don’t feel great about what you’re peddling, how can you expect anyone else to?

Complacency

No founder wants to admit that they’re complacent, but the truth is that for periods of time, many of us do arrive at this reality. Maybe we sold a company, bought a house, had a kid, or just got burnt out of the 24/7 ambition that got us here. It’s completely fine to acknowledge that reality, and in fact, I’d argue it’s better to admit it than deny it. However, it’s also important to assess whether we’re complacent for a reason, for a season, or for forever.

Sometimes, burnout takes an irreversible turn and we’re truly checked out of a venture that was once our bread and butter. That just may be the catalyst we need to shake things up, perhaps sell the company, and set our sights on a new pursuit that may be more exciting. I recently went to dinner with a couple of founder friends who wound up in this exact position, and they couldn’t be happier:

After five years, some success, and a few shifts in priorities (and some strategic financial rebalancing to cash in some chips and cover their downside), they decided to start shopping around their venture. While it may not be the 8-figure offer they once aspired to, it is a pretty sweet (still lucrative) deal that gives them each a good three years to explore their next opportunity, while cashing much-appreciated paychecks for peace of mind.

If you’re finding your venture boring, empty, or unfulfilling such that you know you aren’t bringing your A-game anymore, it may be time to let a new player step up to the plate. There is a such thing as a “win-win” change of ownership, and sometimes new blood is the missing puzzle piece.

A happy ending

Let me clarify: I’m not suggesting a happy ending or idyllic outcome can’t be in the cards for you and your entrepreneurial journey. I’m simply proposing that sometimes clinging to a defined expectation of exactly what that happy ending or idyllic outcome looks like — and doing everything in your power to stay that course — can preclude other (sometimes better) opportunities from taking shape.

Off the top of my head, I can name over a handful of close founder friends whose paths have taken unexpected turns that would have been impossible if they’d clung to the original plan.

My original path would have had me spend years pitching a venture in an industry that would soon collapse had I been too narrow-minded to cut the cord and course-correct.

A good friend of mine expected his first startup would be his lifelong pursuit. Flash forward five years, he ended up selling it prematurely (three years before it would have likely become obsolete), pivoting into another venture that gave him early access to a booming industry that kicked off his VC career. He’s since become one of the most successful venture capitalists his age, all because he was brave enough to stray from what he initially thought was his one shot at success.

Success in startups requires mastering the delicate balance of knowing when to overcome obstacles and push forward versus when to take that resistance as valid feedback to pivot or tweak your own product, service, plan, or strategy. To that end, we can all want and strive for (and hopefully achieve) a happy ending, but that may take letting go of the rigidity around what that looks like.

Why you aren’t successful (and won’t be)

At this point, you likely already know my answer — and it isn’t limited to the five toxic factors above, nor is it some trick question surrounding the different definitions of success for each person. It comes down to the fact that success, being rented, is not a static, perpetual endpoint like a finish line at a race. Instead, success is a perpetually moving target, and it’s one you’ll have to keep hunting down and chasing after for years on end if you want it to keep its luster upon arrival.

The good news: You may be at your highest high, but that doesn’t mean you’ve peaked and it’s all downhill from here. Similarly, you may be facing a challenge, a valley, or a lull that has you questioning if you’ll ever get there (or get there again, if you’ve been before). The good news is that so are we all, from those newbie founders hitting their first stride (before their first obstacle), as well as those career entrepreneurs with 9-figures in the bank, yet perpetually thirsty for more knowledge and hungry for their next great challenge.

The journey is constant, the destination dynamic, and the reinvention of your next A to Z pursuit as unpredictable as everyone else’s simultaneous, yet completely different paths to a perpetually moving, yet endlessly rewarding target.

5 Things You Need to Delete to Acquire Startup Success (Even if You’ve Already Been Successful) was originally published in Entrepreneur's Handbook on Medium, where people are continuing the conversation by highlighting and responding to this story.

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