You’ve seen the posts. A founder standing in front of a private jet or a minimalist office, captioning a photo with some variation of "we finally made it." It’s a nice sentiment. It sells courses. But in the world of actual business operations and scaling, the phrase when we make it is basically a mirage.
It doesn’t exist.
Most people think of "making it" as a fixed destination—a specific revenue target, an acquisition, or maybe just the moment the bank account has enough zeros to stop the late-night panic attacks. But if you talk to anyone who has actually scaled a company from a garage to a Series C or a stable mid-market firm, they’ll tell you the goalposts don't just move. They vanish.
The psychological trap of when we make it
There is a specific kind of mental fatigue that comes with chasing a finish line that isn't there. Psychologists call this the "arrival fallacy." It's the belief that once you reach a certain milestone, you'll experience lasting happiness or a sense of "completion." In business, this is dangerous. When we make it becomes a justification for burnout. You tell yourself you’ll sleep once the product launches. You tell your family you’ll be present once the funding round closes.
The problem? The launch leads to bugs. The funding leads to higher expectations and more aggressive hiring targets.
Take the case of Basecamp founders Jason Fried and David Heinemeier Hansson. They’ve been vocal for years about the "myth of the hustle." They argue that the obsession with a future state of success prevents business owners from building a sustainable "calm" company today. If your entire operational strategy is built around a future date when we make it, you are likely neglecting the infrastructure needed to survive the journey itself.
Real growth isn't a mountain
It's more like a treadmill that occasionally changes incline.
I remember talking to a SaaS founder who hit $10 million in Annual Recurring Revenue (ARR). That was his "make it" number. He thought the stress would evaporate. Instead, he realized that at $10 million, his customer support team was breaking, his legacy code was a mess, and his original employees were burnt out. He hadn't "made it." He had just unlocked a more difficult level of the game.
Why the market doesn't care about your finish line
Investors and customers don't care about your personal sense of arrival. They care about "what's next." The phrase when we make it implies a stop. But the market is a river. If you stop, you get pushed backward.
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Look at companies like Kodak or Nokia. They "made it" by every conceivable metric in the 90s. They owned their respective markets. But because they acted like they had reached the destination, they stopped innovating at the pace required to survive the digital shift.
The nuance of "The Messy Middle"
Scott Belsky, the Chief Product Officer at Adobe, wrote extensively about this in his book The Messy Middle. He points out that the beginning and end of a venture get all the press. The "make it" moments are what people put on LinkedIn. However, the actual value of a business is created in the volatile, boring, and often painful middle section.
If you're waiting for a moment when we make it to feel successful, you're going to miss the actual work that defines your legacy.
- Success is a lagging indicator.
- The "win" happened months ago in a boring meeting.
- Celebrate the process, not just the wire transfer.
Defining your own version of "making it"
If the traditional definition is a lie, how should you actually measure progress? You have to get granular. Instead of a vague idea of when we make it, look at specific, repeatable wins.
Is it when you have 90% customer retention?
Is it when your team can run the company for a month without you checking Slack?
Is it when you’ve hit a specific profit margin that allows for 20% R&D reinvestment?
These are tangible. They are also temporary.
I once worked with a retail brand that thought "making it" was getting into Target. They got the deal. It almost bankrupted them because their supply chain wasn't ready for the volume. They had focused on the trophy (the shelf space) rather than the engine (the logistics). Their when we make it moment turned into their biggest nightmare because they hadn't defined success by operational health, but by external validation.
The pivot from destination to durability
The most successful entrepreneurs I know have stopped using the phrase when we make it entirely. They’ve replaced it with "how we stay here."
This shift changes everything.
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- Hiring changes: You stop hiring "hustlers" who will burn out in six months and start hiring "builders" who want to create systems.
- Product changes: You stop shipping "minimum viable products" that are held together by duct tape and start focusing on technical debt and scalability.
- Personal life changes: You realize that if there is no finish line, you might as well take a weekend off now.
Honestly, the "making it" mindset is kinda like a drug. It gives you a high, but the crash is brutal. If you’re waiting for the world to tap you on the shoulder and say "You're done, you've won," you're going to be waiting forever.
Actionable steps for the "post-arrival" mindset
Stop looking for the horizon and start looking at the ground. If you want to build something that lasts, you need to abandon the idea of a final destination.
- Audit your "When" statements. Write down every time you say "I'll do X when we make it." If those things are essential for your health or the company's culture, do them now.
- Define "Operational Peace." Instead of a revenue goal, set a goal for how many hours a week you want to work or how many days a project should take to complete without overtime.
- Kill the "Trophy" metrics. Stop obsessing over Forbes 30 Under 30 or industry awards. They are vanity signals that have zero correlation with long-term profitability.
- Build for the "In-Between." Optimize your daily workflow so that the "messy middle" is actually enjoyable. If you hate the day-to-day, no amount of money at the end will make it worth it.
- Interview your "Heroes." Reach out to someone 10 years ahead of you. Ask them if they feel like they've "made it." Spoilers: They don't. They just have bigger problems and better tools to solve them.
The reality of when we make it is that it's a moving target. You hit one peak, and you just see a higher mountain behind it. That's not a bad thing—it's just the nature of growth. Embrace the climb, because the summit is just a place to catch your breath before the next leg of the journey.