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Entrepreneur Down Days: What I Do When Nothing Goes Right

Entrepreneur Down Days: What I Do When Nothing Goes Right

October 07, 2026•4 min read

Entrepreneur down days are the days when nothing goes right, you feel low and you wonder whether to carry on. Today was one of them. It is Day 2,094 of my daily barefoot-style running streak, and I will be honest: I felt flat before I took a single step.

I record these episodes while I run, and I notice something each time. Once the camera is on, I feel I owe the audience a more positive version of me. So thank you for that. Pressing record lifted my mood more than I expected.

What happened today

The property business is taking hits from several directions at once. Tenants are vacating. Major maintenance has landed. A boiler needs replacing. All of this arrives together, and all of it cuts into profit.

At the same time, I am in an optimisation phase. I am investing a significant amount to lift the standard of a number of properties, so we attract better tenants, achieve higher rents and improve returns. I know this is the right decision. Knowing does not make the costs arrive any more gently. Money goes out for the repairs and out again for the improvements, and the benefit comes later.

Then came the furniture. My builder, one of my business partners and I are converting two properties to serviced accommodation. Both need fully furnishing. We drove to a wholesaler in the Midlands, loaded the van and fitted in nearly everything. Two boxes would not go in. I delivered the first load, then drove back for the rest. That was a four-hour round trip for two boxes.

You might ask why I do not pay someone else. Normally I would agree. In this case I estimate outsourcing would cost around four times as much, and flat-pack furniture is not specialist work. We have done this before. Three of us blitz two properties over a couple of days and get a better return on our time than a third party would give us. We will work into the early hours to recover the lost time. Knowing the plan is sound did not stop the frustration.

Meanwhile, messages kept arriving through every inbound channel. A low day rarely has a single cause. Several small weights stack up.

What I take from it

First, I treat a down day as normal. The figure often quoted is that 90% of businesses fail. I have been an entrepreneur for over 20 years, and I have seen the highs, the lows and most of what sits between. If you run a business, expect more hard days than easy ones. Expecting them does not remove the feeling, but being realistic about it helps me handle it with less drama.

Second, I do not hide from the day. There were moments today when I wanted to bury my head and go to sleep. Sleep does not solve a boiler or a delivery. The problems are still there when I wake.

Third, I need a way to release stress, pressure and overwhelm. Mine is running and vlogging. Yours could be different. The point is to have a process in place before the bad day arrives, rather than inventing one in the middle of it.

Fourth, clarity follows release. When my head is clear, most of the problems in front of me turn out to be fairly straightforward. When I am overwhelmed, I freeze like a rabbit in headlights. Stepping back, even for a few kilometres, changes how the same list of problems looks.

A small moment from the run

Earlier in my streak I ran across fields near Burnley and ended up almost waist deep in mud. Today I saw a large mud bath ahead and went round. It is a minor detail, but the principle applies to bad days too. You learn from the last one, and you pick a better line.

Why I keep going

Today's run took me to 16,128.83km in total. That leaves 23,946.17km to complete a lap of the world at 40,075km. The distance is long, and I expect many more days like today along the way. Consistency means running on the good days and on the flat ones, because the streak does not pause for my mood.

The run is also part of a fundraiser. My aim is to raise £1M or more for children's causes, including Great Ormond Street and BBC Children in Need. The more people who watch, the more people hear about the mission, and the more support children's causes receive. My bad day sits small beside the reasons for the mission, and recording it reminds me of that.

If you are having a down day as you read this, I hope this helps. Know it is normal. Find your release. Get clear, then deal with the next problem in front of you. Tell me how you handle your own low days in the comments. I read them and respond to anything relevant.

If you want to support the mission, watch the vlog, subscribe and share it with someone who might need it. I will be back out tomorrow for Day 2,095.

Watch the full episode: https://youtu.be/5Khw4_PDM_M

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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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