A Founder’s Compass: Questions to ask before you quit your startup

Sharing a straightforward framework called The Founder's Compass with you so you can check for yourself if you're still aligned with your startup's direction

TL;DR  
* I just pulled the plug on my startup, a sock brand called This Is Not Fashion
* This is Part 1 of a 2-part series: the key questions I used to decide whether to quit
* The framework is called The Founder’s Compass, built around alignment with your North Star
* I also share a mindset shift: Building conviction by placing intentional bets and knowing when you’ve run out of them

Why it matters

When should you walk away from your startup?

It’s an entrepreneur's perpetual question when things don’t seem to work out.

On the one hand, you and I both know it’s about grit. It’s about persistence. You don’t just give up after the first setback.

But on the other hand, maybe something is off? Maybe you’re no longer aligned with the vision. Or the product turned out differently from what you expected it to be. Then why continue working on it? Why suffer?

Then there’s also the opportunity cost. What if I were working on something else? Are my skills and efforts better suited elsewhere?

So, before calling it quits, understand this: Is it simply a matter of pushing through now, or is there insurmountable misalignment?

And what about timing? Can you walk away “too early”?

A Founder’s Compass

Before we go to the questions, I want to introduce a simple analogy that helped me make sense of them: A Founder’s Compass. You know, that internal tool you use to see if you’re still on track.

I won’t pretend I had this framework fully formed when I made my decision. But the questions were there - some I asked myself, others came from people in my sounding board.

The compass has just three elements:

The North Star - Objectively, the goal of the startup

The North Star

True North - The direction pointing to the North Star

The True North points to the North Star

Your Heading - The path you’re currently taking

Where you’re actually going

The Questions

With our Founder’s Compass in hand, we can now ask ourselves some reflective questions about the past, present, and future. Or put differently: They’ll force you to think about your journey seen from the Starting Point, your Current Location, and the position of the North Star.

The Starting Point, your Current Location, and the position of the North Star

The Starting Point (Past)

Go back to where you started and ask yourself these questions:

• Why did I even start in the first place?

  • This reminds you of what motivated you to embark on this journey

• Is that spark still here?

  • Do you still want to solve this problem, or do you just want it to succeed already?

The Current Location (Present)

Take time to reflect on the present through these questions:

Where am I now? Have I veered off-course too much?

• This is about understanding where you are now and if the Heading you were following was matching the True North

The Heading you were following versus True North

• Can I course-correct?

  • If you’re off-course, are there ways for you to realign Your Heading with the True North? If yes, go make that move

A New Heading: Course-correct your old Heading to the True North

• If not, what’s holding me back from continuing in the direction of the North Star?

  • What resistance are you feeling? What objections can you raise?

  • Can you overcome these objections?

The North Star (Future)

Think about the clarity and the validity of the startup’s goal:

• Where is the North Star?

  • Do I have a clear view of what it means to make this startup a success?

• Do I agree with the position of the North Star?

  • Do you still believe this is the right goal to pursue? Does it align with your values and long-term direction?

  • Or are you unconsciously playing to lose rather than win because, in the back of your mind, you really don't want to win?

• If not, is there a way I can pivot this into something else that’s meaningful?

  • Helpful questions for that are:

    • What excited you most about the journey so far?

    • What have you learned that could help you reposition your North Star?

Repositioning the North Star

Time to call it quits

When is the right time to reflect on when to quit? Is there a thing as giving up too early?

To stop guilt-tripping yourself, I think it’s helpful to look at these 2 questions through the concept of building conviction by placing bets.

When you embark on your journey, you may have an inkling of an idea of how to get to the North Star, but you aren’t sure how to get there. For that, you need to start building conviction.

You make a bet - you run an experiment - that the next step is leading you in the right direction. For every bet that is validated, you become more certain, and you start walking more confidently. But for every bet that is invalidated, you try to interpret what went wrong, and you try again.

When is the right time to reflect on when to quit?

So, after how many unsuccessful bets do you stop? I wish there’s a number I can give you, but I think this comes down to when you’ve run out of intentional bets you can place. What I mean is: Are there any hypotheses left around the problem statement or the solution that you haven’t tried yet? If the answer is “No”, taking the step to reflect on quitting isn’t failure. It’s about understanding if you’re still smart about using your limited time and energy.

Am I giving up too early?

In effect, that also means that the time you spent on your startup doesn't matter. The question is: Did you spend that time intentionally? As long as your bets were aimed at uncovering the True Heading, then there is no such thing as time wasted. And if you’re running out of hypotheses to prove, then you’re not giving up. You’re saying: “I’ve placed enough thoughtful bets to know this isn’t for me anymore.”

Will I regret walking away from this now?

You can also flip it around by asking yourself: Will I regret walking away from this now? If the answer is “No”, then you’ve probably tried all you could. But if something is still lingering there, you may want to figure out what that is.

Conclusion

I hope that by going through the Founder’s Compass and its questions, you’ve now come to learn about how you can check if you’re still aligned with your startup’s direction. I’ve also given you the concept of building conviction through placing bets (and running out of intentional ones) to get a feel for the timing of your introspection.

If you want to see how I’ve applied this myself, read Part 2 here or click below!