What Should My Expectations Be?

Our happiness is directly proportional to our expectations. So what if we completely botch our expectations for how well our startup should do?

In over 30 years of helping Founders and most certainly in my own journey, I have never, ever heard a Founder give me a set of expectations that seemed perfectly reasonable.

For some reason, we all sprint into this abyss with the most insane expectations of how our startups are supposed to perform with almost zero grounding in either reality or reason.

While that may sound optimistic and exciting, it's also a giant recipe for failure and disappointment. Not because we're not awesome, but because what we assumed success would look like doesn't even remotely resemble reality.

The Snowflake Myth

Of course, it's fashionable to think big. It drives excitement and lures all of the resources that we need to make something incredible out of nothing. We go into this thinking, "This could be the next Uber or Shopify or Spanx" but the statistical reality of that is 0.003%. A fraction of a fraction of a fraction of 1%.

You see, that's where it starts.

At which point the dream becomes an expectation. Like right around the moment we take investor money or start handing out stock options, we begin setting ourselves up for disappointment. It'd be the equivalent of betting your entire paycheck on a Powerball lottery ticket. Yes, it could absolutely happen. But I wouldn't recommend getting your hopes up.

That doesn't mean we can't dream big; it means that we shouldn't expect it. We should align our expectations with milestones that are earned in succession. That might mean getting a product shipped this year or getting to break even by next year. Those are expectations that align with real work and reasonable outcomes.

The 3X Rule of Time

A key ingredient of expectations involves time frames. How long should it take for this product to get product/market fit? How long should it take to become profitable? How long until we can make Elon money?

Short answer — take whatever expectation you have, and multiply it by 3x... at least. If you think it'll take you a year to get to profitability, try 3 years. If you think it'll take you 3 years to scale to infinity, try a decade.

Expecting things to happen at a freakishly unnatural pace is dangerous.

Startups are like children — they take time to nurture and grow — and that's OK. Even the fastest-growing companies like Uber, Airbnb, and LinkedIn took a decade to get to the public market. And those are the all-time hall of famers.

The reason it's dangerous to set unreasonable expectations on time is that we're artificially forcing bad decisions. We cut product before it can mature. We abandon marketing channels before they can develop. We pivot our whole company before we know what we're building.

But when we expect things to take time, we align them with a more natural order of evolution. It's the same reason my 9-year-old son isn't going on to the NBA already. That, and he's 4 feet tall.

The Entitlement Trap

We're also not entitled to our expectations. It's like I tell my 9-year-old son, "Just because you want something doesn't mean you deserve it. You deserve it when you earn it." Then I plunder his Fortnite loot crate and run away in the game with his treasure.

We are all victims of our own entitlement. In the startup world, this has massive ramifications because we build expectations tied to our effort. We believe that all of the effort we've expended is entitled to a favorable outcome, but that's simply not how this business works (I wish it did!)

Simply put, we're entitled to nothing unless we've earned it.

Ideally, we're earning it every day. Every time we set up a successful landing page, recruit a stellar employee, or close a new customer of literally any size. Those are outcomes of merit.

Where it breaks is when we expect to be paid for effort. We bemoan "But I've invested 5 years into this thing!" as if that time owes us a return. If we've invested time or resources into something that has not paid back, we're not entitled to payback; we're accountable for our lack of performance.

The best way to avoid the entitlement trap is to reward outcomes, not expectations.

Setting Reasonable Expectations

Which brings us back to "what ARE reasonable expectations?"

It turns out, it's not a single expectation at all. It's a series of compounding expectations that evolve over time. Personally, I prefer to set my windows incredibly short and my outcomes to be aggressive, but achievable.

When I want to lose weight, I don't expect to lose 15 pounds. I expect to lose 1 pound, and until I achieve that goal, which isn't always a given, I don't even think about being entitled to the rest.

There's something magical about aligning realistic expectations, even as part of a bigger plan. We often actually hit them. This provides the reassurance and fuel to hit another, and another.

But when we set the expectation so far beyond reach, it's really hard to know whether we're even on the path, much less powered up for the next one.

Startups are all about big expectations, and that's great. But if we want to be around long enough to meet those big expectations, we need to re-align ourselves with actually surpassing the smaller ones along the way.

In Case You Missed It

Should Startups be a Family? Running a startup isn't a group hug. Keep the vibes real but the roles clear. Authority fades fast when everyone's "family."

Why I'm Either Working or Feeling Guilty How can we achieve a harmonious equilibrium that allows us to pursue our entrepreneurial dreams while also nurturing our mental and physical health and maintaining meaningful relationships?

Will the Payout be Worth the Sacrifice? An honest look at the allure of success and the even deeper question: is the payoff truly what you want?