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Hi, I’m Dima, solo founding father of bootstrapped PitchBob — a tool designed to help aspiring entrepreneurs bring their ideas to life.
I need to start with a disclaimer: my foray into entrepreneurship is not my first. I have had extensive experience building businesses in the past, and my decisions at PitchBob are well-informed. Whether bootstrap or solo, these were calculated decisions, not mere accidents.
Yet despite this experience, I am unable to let you know how many times I’ve struggled with the urge to quit, whether it was stopping progress, changing direction, or quitting altogether. These thoughts come to mind whilst PitchBob has remained the center of my attention, time and financial resources for the past two years.
As the yr comes to a close, I find myself reflecting on deadlines – self-imposed checkpoints to assess whether PitchBob has “taken off” or if it’s time to face the hard truth. The concept of startup success often stays fluid, and this ambiguity can create space for internal negotiation: Should I proceed, or is it time to move on?
Startup analogy: assessing progress
I often compare latest ideas to an airplane speeding down a runway. The engines are roaring, the plane is gaining speed, the wings are vibrating, but it has not yet lifted off the ground. In moments like these, the captain seems like he’s in control… except for one thing: the finite length of the runway.
As a founder, it’s your job to evaluate that runway – available time, resources, and market opportunities. Is there enough momentum to take off? Should you be pushing forward, or is it time to pull the brakes and pivot?
This analogy provides a framework for one of the most difficult questions entrepreneurs face: When must you quit and when must you redouble your efforts? This is a universal dilemma, epitomized by the famous image of a miner walking mere inches away from mining for gold.
Is entrepreneurship a type of addiction?
The line between passion and obsession is thin. Entrepreneurship can sometimes feel like an addiction – an insatiable desire to build, create, and succeed, even in the face of mounting evidence that something is not working. Blindly believing in your vision, ignoring harsh market feedback, or stubbornly pushing forward despite red flags often leads to failure.
Worse yet, the emotional ups and downs of running a startup can mirror the cycle of addiction. The excitement of bringing a product to market, closing a deal, or securing financing is quickly followed by a crushing downfall when things don’t go according to plan.
So how do you know if you are pushing too hard?
How to avoid the trap of throwing away good money, time and energy in exchange for bad?
To solve this problem, let’s examine eight key signs that help founders decide whether to persevere or let go.
When to let go
1. No progress despite effort
If months (or even years) of concentrated effort have produced little or no progress, consider whether the problem is market demand slightly than execution.
2. Constant negative feedback
If customers, partners or investors consistently resist, it’s time to re-examine your assumptions. Sometimes the market just is not ready and is not interested.
3. Personal well-being declines
If your startup is harming your health, funds, or relationships, that is a red flag. No business idea is value personally destroying.
4. The runway is gone
If you have exhausted your financial, emotional and worldly resources, it could be higher to land the plane slightly than risk disaster.
When to persevere
1. You see the grip
Even small signs of customer or user engagement can signal that your idea has potential. Sometimes a few tweaks can unlock significant growth.
2. There is a clear path forward
If you have identified actionable next steps that may move the needle, it’s value staying the course.
3. External validation
The support of reliable investors, partners or advisors can confirm your faith in the enterprise and provide the mandatory resources for its continuation.
4. Your passion still burns shiny
Passion will be the fuel that powers perseverance. It may be value pushing through if you are still excited about solving the problem.
Balance of grit and realism
Entrepreneurship often glorifies grit – “Never give up” is a mantra we have all heard. But the reality is more nuanced. While persistence is key, equally vital is the ability to judge when an endeavor has reached its natural end.
The key is honest self-reflection. By assessing your runway, understanding market feedback, and knowing your personal limits, you’ll be able to make balanced decisions about when to double down and when to switch.
The path to success
Success is not linear. Sometimes the best decision is to change direction, start over, or even leave altogether. Knowing when to quit will be just as vital as knowing when to persist.
After all, failure is not the opposite of success – it is often a step towards it.
Founders facing this decision should do not forget that in search of outside perspectives will be helpful. Whether it’s a mentor, a fellow entrepreneur, or a trusted advisor, they’ll provide the clarity you would like to assess your runway and determine your next steps.