When working harder stops working: a founder’s perspective

I can’t pinpoint when working harder stopped helping in my first business. It was a long time ago.

What I remember is feeling overwhelmed and tired, and not understanding why the results weren’t coming. Looking back, I think I sold that business about three years too late.

I’d like to be able to describe the moment I recognised what was happening and changed how I worked. But I can’t honestly say there was one.

That’s part of the difficulty. When you’re inside a business, carrying the responsibility and trying to keep things moving, it can be hard to recognise when more effort is no longer helping.

Effort can become your answer to every problem

There are times when building a business requires a push. A customer needs attention, something breaks or an important deadline is approaching. You put in the hours because there is a specific job to finish.

The harder question is what happens when the push becomes your normal way of working.

You work longer, but the same problems keep returning. You get through the immediate demands, but the decisions that might change things remain untouched. You finish the week exhausted and struggle to say what has actually moved forward.

Working harder is an understandable response. It gives you something to do when the outcome feels uncertain. You might not know whether a new approach will work, but you know how to put in another hour.

Over time, though, effort can become a habit you stop questioning.

What is the extra work actually achieving?

Before deciding how to become more productive, it’s worth looking at what your work is doing.

Think about the last couple of weeks:

• Which activities moved the business towards something important?

• Which kept it operating but left the underlying problem unchanged?

• Which did you take on because it felt easier than explaining, delegating or saying no?

• What important decision did you keep postponing?

Keeping a business operating matters. There will always be routine work, and every hour doesn’t need to produce a breakthrough.

But if your involvement is repeatedly needed to resolve the same issue, that deserves attention. Perhaps responsibility is unclear. Perhaps the team needs support. Perhaps you’re continuing to offer something that takes more out of the business than it contributes.

Those possibilities call for different responses. More hours won’t tell you which one you’re dealing with.

Some decisions need attention before they feel urgent

Looking back at my first business, I believe I stayed in it too long. That is much easier to say now than it was to recognise then.

I don’t have a neat explanation for those three years. But the experience leaves me with a question I think is useful for founders:

What are you continuing with that you would hesitate to choose again today?

It might be a product, a customer relationship or a way of working. It could be the role you’ve created for yourself.

That question doesn’t mean you should immediately stop, sell or walk away. There may be good reasons to continue. It gives you permission to examine the decision instead of treating it as already settled.

You can also ask:

• What would need to change for me to want to keep doing this?

• What evidence supports continuing as we are?

• What would make me reconsider?

• When will I properly review this decision?

Without a review point, “I’ll give it a bit longer” can become a decision that keeps making itself.

Your state deserves a place in the conversation

When you’re tired and overwhelmed, it can be difficult to separate the demands of the business from how you’re experiencing them.

A problem may need urgent action. You may also need enough space to understand it before acting. Both can be true.

This is why I think questions about the founder belong alongside questions about the business.

How much capacity do you have? Are you able to think beyond the next demand? Do you have someone you can speak to without feeling you need to sound confident or have an answer ready?

Those questions won’t resolve a cash flow problem or repair a difficult customer relationship. They can help you recognise the conditions in which you’re trying to make those decisions.

Your energy and attention are part of how the business is being run. They deserve consideration.

Create enough structure to see what’s happening

When everything feels full, adding another system can sound like more work. Start with something small enough to use.

Set aside a regular time to step back from delivery and review three things:

What matters most now?Choose a small number of priorities that reflect what the business actually needs. Be clear about what can wait.

What keeps coming back to me?Look for repeated decisions, problems and requests. Is your involvement necessary, or has it simply become the usual route?

What needs a decision?Separate something you need to do from something you need to decide. “Work on sales” can stay on a list indefinitely. Deciding which customer group to focus on gives that work a direction.

Finish by choosing one change to test. It could be clarifying who owns a decision, stopping a low-value activity or having a conversation you’ve been avoiding.

Give yourself a date to review whether it helped. The point is to learn what changes the situation.

Find someone who can help you examine it

You may already have people offering advice. What can be harder to find is a conversation where you can admit that you don’t know what’s happening.

That might be with a trusted peer, a mentor or a coach. Depending on the issue, you may need a specialist who can help you understand a particular part of the business.

The useful starting point is being able to describe the situation honestly, including the parts that don’t fit the story you usually tell about how things are going.

Someone outside the daily demands may notice an assumption you’ve stopped questioning. They may ask why a responsibility still sits with you or help you distinguish a temporary difficult period from something that needs to change.

You still make the decisions. You have more room to examine them.

A question to start with

I wish I could offer a simple account of recognising this pattern in my own businesses and putting it right. My experience was less tidy than that.

What I can do now is encourage founders to look at the relationship between their effort and the results they’re getting before exhaustion becomes the only reason to stop.

If you’re working harder and still feeling stuck, ask yourself:

What am I expecting more effort to solve, and what else might this situation need?

You don’t need an immediate answer. It’s a useful question to make time for.

If this feels familiar, my founder coaching and mentoring offers space to think about your business, your role and what needs your attention. We can begin with a free introductory conversation.

Cheers,

Duncan