What’s your why? Understanding what matters to you as a founder
Updated: Oct 7
Why did you start your business, and how much does that reason still influence the way you run it?
You may have wanted independence, spotted an opportunity or felt frustrated by a problem you knew you could solve. Perhaps you wanted to earn a better living or build something with people you respected.
Those reasons can change as the business grows.
The work becomes different. More people depend on you. A company that originally offered freedom can begin to fill every available part of your life.
Making time to understand what matters to you can help you make decisions about the business you want to lead and your place in it.
Start with what is true for you
The question “What’s your why?” can create pressure to produce an inspiring answer.
You do not need a grand statement. You need an honest understanding of what makes the work worthwhile to you.
Money, security, independence, curiosity and the satisfaction of doing something well can all be part of that answer. You may care deeply about solving a customer problem while also wanting more control over how you spend your time.
Allow for more than one motivation. Trying to compress everything into a single sentence too early can hide useful differences.
You might love building something new but enjoy managing an established organisation much less. That is worth understanding before assuming that every stage of growth will suit you equally well.
How I arrived at my own why
Working through Simon Sinek’s process for finding your why helped me put words to what matters most in my work.
Looking back at experiences that had been meaningful to me, I could see a recurring theme: connecting with someone and helping them make progress that mattered to them.
Earlier in my career, I associated that satisfaction with sales. I enjoyed understanding a customer’s problem and providing something useful. But the part that mattered most was seeing what our work together made possible for that person.
That thread runs through my coaching and mentoring today. The way I now express my why is:
To deeply connect with others to enable transformations they couldn’t achieve alone.
For me, that means building a relationship where a founder can speak openly, question their assumptions and work through decisions they find difficult to make on their own.
I bring attention, questions and relevant experience. The decisions remain theirs.
Arriving at this wording helped me recognise the connection between work I had enjoyed in the past and the contribution I want to make now. It also gives me something to return to when considering how I work and where I put my energy.
You can begin your own reflection by looking at specific experiences. When did your contribution feel most worthwhile? Who were you helping? What was it about that moment that mattered?
Consider experiences outside work too. You may find a similar theme running through different parts of your life.
Notice what frustrates you
Frustration can provide another starting point.
Think about situations that repeatedly leave you dissatisfied. Is it the work itself, the way decisions are made or the expectations surrounding it?
You might feel frustrated when you cannot do work to the standard you believe is right. You might resent having no say in your schedule or find it difficult when people avoid honest conversations.
Explore what sits behind that reaction.
For example, wanting independence could mean choosing which problems to work on, controlling your hours or having the final say. Those are different needs, with different implications for how you build a business.
Be specific enough that the insight can inform a decision.
Separate your priorities from other people’s expectations
Founders encounter plenty of views about what success should look like.
Raise investment. Grow faster. Build a larger team. Become a recognised name. Sell the business.
Any of those could fit your ambitions. They can also become goals you pursue without examining whether you want what comes with them.
Ask yourself:
Which ambitions feel like mine?
What am I pursuing because it is expected?
What would still matter if nobody else knew I had achieved it?
What am I willing to take on to reach this goal?
What am I unwilling to sacrifice?
Be honest about the trade-offs. Wanting growth and wanting more personal freedom are not necessarily incompatible, but achieving both may require deliberate choices about pace, ownership and your role.
Connect what matters with how you work
Your priorities become useful when they influence behaviour.
If developing people matters to you, where do you make time for it? If independence matters, which commitments are increasing or reducing it? If you value honesty, how do you respond when someone tells you something difficult?
Look at your calendar, recent decisions and the promises you have made. Do they reflect what you say matters?
A mismatch does not mean you have failed. It gives you something concrete to examine.
You may discover that your priorities need more attention, that circumstances require a temporary compromise or that your understanding of what you want has changed.
Make room for changing motivations
The reason you started does not have to remain your main reason for continuing.
You may have begun by wanting to prove something to yourself. Years later, you might care more about the team, the quality of the work or having time for other parts of your life.
Equally, work you once enjoyed may now feel repetitive, while a new challenge holds more interest.
Revisit these questions when the business changes or when you notice that familiar goals no longer feel satisfying.
Before making a major change, explore what has shifted. Are you tired and in need of support? Has your role become a poor fit? Or do you want a different direction?
Those possibilities deserve different responses.
Use your reasons to question persistence
Knowing why something matters can help you decide which difficulties you are willing to work through.
It should also leave room to question the approach.
Caring about your customers does not require you to keep offering a product they do not want. Valuing your team does not mean avoiding difficult decisions. Wanting to build a worthwhile business does not require you to continue in exactly the same role indefinitely.
Ask whether the current plan still serves the purpose behind it.
You may need to persist, change the method, reduce the scope or stop something. Your reasons for doing the work should help you examine those choices honestly.
Try a short reflection
Set aside some uninterrupted time and write a few lines in response to these questions:
When has my work felt most worthwhile?
What was I contributing in those moments?
What do I want the business to make possible for me and others?
What am I currently accepting that conflicts with that?
What is one decision I could make differently as a result?
These are starting questions for reflection, rather than a reproduction of Simon Sinek’s full process.
Look for patterns without forcing a neat answer.
You could discuss your reflections with someone who knows you well and is willing to challenge you. Ask what they recognise and where they see a difference between your words and your actions.
Keep your notes and return to them. Their value lies in helping you notice and decide.
Decide what this means for the next stage
You may finish this reflection with greater clarity about why you want to grow. You may realise that you need a different role, firmer boundaries or a conversation you have been putting off.
Choose one practical implication to explore.
Understanding what matters to you will not remove the demands of running a business. It can give you a clearer basis for deciding which demands to accept and how you want to respond.
If you would value space to explore your motivations, your role and what you want from the next stage of your business, explore working with me through founder coaching and mentoring.
Cheers,
Duncan
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