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Hello everyone, I am Dima, a self-made independent founder. pitching bob — Tools designed to help aspiring entrepreneurs turn their ideas into reality.
First I want to make a disclaimer: my entrepreneurial journey is not my first. I have extensive experience building businesses in the past, and my choice of PitchBob was well thought out. Whether you’re bootstrapping or going it alone, these are carefully considered decisions, not just accidental.
Yet despite this experience, I can’t count the number of times I’ve struggled with the urge to quit—whether it was freezing progress, rotate Or walk away completely. These thoughts come to me even though PitchBob has remained the central focus of my attention, time, and finances for the past two years.
By the end of the year, I find myself reflecting on deadlines—self-imposed checkpoints to evaluate whether PitchBob has “taken off,” or if it’s time to face the hard truth. The concept of success in a startup is often fluid, and this ambiguity can create room for internal negotiations: Should I stick with it, or should I move on?
Takeoff Metaphor: Assessing Progress
I often compare new ideas to being in a plane speeding down the runway. The engines roared, the plane accelerated, its wings twitched—but it hadn’t left the ground yet. In moments like this, the captain feels like he has everything under control…except for one thing: the runway is limited in length.
As a founder, your job is to assess the runway—the time, resources, and market opportunity available to you. Is there enough power to take off? Should you push forward, or brake and swerve?
This analogy can serve as one of the most important frameworks challenging questions Entrepreneurs face: When should you quit smoking and when should you try harder? It’s a common dilemma, epitomized by the famous image of a miner inches away from striking gold.
Is entrepreneurship an addiction?
there is a thin line between passion and obsession. Entrepreneurship can sometimes feel like an addiction—an insatiable drive to build, create, and succeed, even in the face of mounting evidence that things aren’t working. Blindly believing in your vision, ignoring tough market feedback, or stubbornly pushing ahead despite danger signals often leads to failure.
Worse, the emotional rollercoaster of running a startup may reflect a cycle of addiction. The excitement of launching a product, closing a deal, or securing funding can quickly take a downturn when things don’t go as planned.
So, how do you know when you’re pushing too hard?
How do you avoid falling into the trap of investing money, time, and energy after something bad happens?
To address this issue, let’s look at eight key signs that can help founders decide whether to persevere or give up. let go.
when to let go
1. Lack of progress despite efforts
If months (or even years) of concentrated effort produce little to no progress, consider whether the problem is market demand rather than execution.
2. Continuous negative feedback
If customers, partners, or investors continue to resist, it’s time to revisit your assumptions. Sometimes, the market is simply not ready or interested.
3. Personal happiness is declining
If your new startup is harming your health, finances, or relationships, that’s a red flag. No business idea is worth destroying personally.
4. The runway disappeared
If you have exhausted your financial, emotional, and time resources, it may be better to land the plane than risk a crash.
Related: 7 Signs It’s Time to Get Out of Your Business
When to persist
1. you see traction
Even the slightest sign of a customer or user engagement It shows that your idea has potential. Sometimes, a few tweaks can lead to significant growth.
2. There is a clear path forward
If you’ve identified actionable next steps that you can take action on, it’s worth following through.
3. external validation
Support from a trusted investor, partner, or advisor can reaffirm your confidence in your business and provide critical resources to continue operations.
4. Your passion still burns brightly
Passion can be the fuel for persistence. If you’re still excited about solving the problem, it might be worth sticking with it.
Balancing courage and realism
Entrepreneurship often celebrates courage—“never give up” is a mantra we’ve all heard. But the reality is more nuanced. While persistence is important, so is the ability to assess when a business has reached its natural conclusion.
The key is honesty self-reflection. By assessing your runway, understanding market feedback, and knowing your personal limits, you can make balanced decisions about when to double down and when to pivot.
Related: How to know when to give up, when to pivot, and when to persevere
road to success
Success is not linear. Sometimes, the best decision is to change direction, start over, or even leave entirely. Knowing when to give up is just as important as knowing when to persevere.
After all, failure is not the opposite of success—it is often a step toward success.
For founders facing this decision, remember that it can be helpful to seek an outside perspective. Whether it is a tutorother entrepreneurs, or trusted advisors who may provide you with the clarity you need to assess your runway and determine your next steps.
