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Entrepreneurial Overwhelm: What I Do When Everything Goes Wrong at Once

Entrepreneurial Overwhelm: What I Do When Everything Goes Wrong at Once

October 03, 2026•5 min read

Entrepreneurial overwhelm is not something I talk about often, but this week it caught me. Today is day 2081 of my daily run streak, and I have now covered 16,047.32km of the 40,075km I need for a lap of the world. That leaves 24,027.68km. The running goes on whatever else is happening. The business side of this week did not go to plan.

Last week ended well. It was productive, and I was on track to finish what I had set out to do. Then this week started and almost everything that could go wrong did. No single problem was fatal. The trouble was the speed and the volume. When issues arrive that fast, I struggle to treat each one on its own. My head starts telling me it is all a disaster, and I drift away from the plan.

If you run a business, you may know this feeling. I like clarity and visibility more than I like control. When I lose sight of the full picture, the noise takes over. That is what happened to me.

I am still working my way out of it, so I will not pretend I have this solved. What I can share is the process I am using today.

Step one is my problem-solving framework, which I call OCI. Treat the problem as an opportunity to solve and grow. Focus only on what you control. Make a plan for those controllable parts. Remove the emotion. Removing the emotion is the hardest part, but working through the other steps in order reduces it.

The framework works well for one problem at a time. It works less well when six arrive in a week, because you do not have the headspace to apply it to each one. So I add a step before it: capture everything.

I dictate every issue into a bullet list. Nothing gets filtered or judged at this stage. I just get it out of my head and onto paper, or the electronic version of paper. This alone brings the pressure down, because a list has an end and a worry in your head does not.

Next I sort the list. I use three levels. Project-based tasks drive me towards my goals. Urgent tasks need doing soon. Not urgent tasks can wait, and some may not need doing at all. I put each new issue against what is already in my workload, so I can see where it fits on a timeline.

Then I look at exposure. What does each issue cost, and what does that do to my cash flow? This part matters more than most business owners admit. Overwhelm often has a money problem underneath it. If you have the right reporting in place, you can see your cash position and place each cost where the cash allows. Some things can move further down the line. Cash flow is dynamic, so a payment that hurts this week may be comfortable in three. The aim is to stay solvent and cash flow positive while you deal with what has landed.

The last step is to bring these issues into my strategic project plan. I treat them as project tasks unless it is obvious they will not affect my goals. They are distractions, and solving them frees me to return to the work that moves the business forward. If I leave them outside the plan, they keep pulling at my attention.

Once this is done, something shifts. The visibility comes back. I stop panicking and stressing and return to what entrepreneurs get most value from, which is executing the plan.

I think about this in the context of the run. Over 2081 consecutive days, not every day has been good. Some runs have happened in poor weather, with tired legs, or with a head full of business problems. The streak has taught me that the next step does not need the whole situation solved. It needs one decision and one action. A rough week is the same. I do not need to fix everything today. I need to capture it, rank it, fund it and schedule it.

The streak also keeps me honest about consistency over intensity. A week like this one tempts me to go all out and try to fix everything at once. That is how mistakes get made. A steady process beats a frantic one, on the road and in the business.

This is why the mission matters to me. I run every day to attempt the ultimate ultra-marathon of run-vlogging, a lap of the world on consecutive days, and to raise £1M for children's causes including Great Ormond Street and BBC Children in Need. The more people who see this, the more support the children get. A bad week in business is a real problem, but it is a small one next to what those children and their families face. Keeping that perspective helps me stay calm and keep going.

If you are in the middle of your own overwhelming week, here is the short version: - Work through your problem-solving framework first. - Get every issue onto paper. - Sort them by project, urgent and not urgent. - Check the cost of each against your cash flow forecast. - Schedule what can wait. - Fold the rest into your plan.

If you are following the run, thank you. If you want to help the mission, subscribe, share, like or comment on the episodes, because every extra viewer helps the children's causes. I will be out again tomorrow for day 2082.

Watch the full episode: https://youtu.be/0Yf5_FRIaQE

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I am on a mission to raise £1,000,000 for children's causes by daily run-vlogging barefoot-style, covering the total distance of a lap around the world—40,075 km.

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