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Entrepreneurial Overwhelm: How a Plan Lifted the Weight

Entrepreneurial Overwhelm: How a Plan Lifted the Weight

October 02, 2026•5 min read

Yesterday I described a bad day. Several things went wrong in my businesses in a short space of time, and I felt entrepreneurial overwhelm in my body. I would not call it a panic attack. It was the feeling of my stomach eating itself, the sort you get when fear takes over. Today is day 2082 of my daily barefoot-style running streak, and I want to report what happened after I put a plan in place.

The short version is this. The workload did not shrink. The weight on me did.

What I did yesterday evening

I used three things. The first is my problem-solving framework, OCI. I frame the problem as an opportunity to solve and to grow, which changes how I approach it before I start. I then separate what I control from what I do not, and I spend my effort only on the first list. Next I build a plan for the controllable parts. Last, I remove emotion and look at evidence.

The second is my strategic project plan. It breaks the steps towards my quarterly goals into weekly, monthly and quarterly pieces. Each issue from the bad day went into that plan alongside the tasks already there.

The third is cashflow. For every issue I put a cost against it and a date by which it needed solving. Then I spread the work out so cashflow stayed protected.

At first glance, adding the issues to the plan looked like it doubled my workload. Once I attached money and urgency to each item, the picture changed. Some things needed action this week. Some needed action next month. Some cost less than they felt like they cost at 2am. I could see the sequence, and I could see the effect on capacity and cash.

The pressure lifted almost as soon as the plan was in front of me. I did not expect it to happen so quickly, and I found it invigorating.

Why the plan worked

Overwhelm is mostly a lack of information. When problems sit in your head, they have no size, no order and no deadline, so they all feel urgent and all feel large. A plan gives each one a size, an order and a date. The problem does not disappear, but your brain stops treating it as a threat.

I also think this is why consistency matters more than intensity. I have run every day for 2082 days. Most of those runs were ordinary. A few were hard. The streak does not rely on feeling good that day. It relies on a decision already made. My planning system works the same way. I did not need to feel calm to open the plan and start filling it in. I needed the system to exist already, so I could use it on a bad day.

The part about partners

I have struggled with business partnerships in the past. I have been through several over the years, and I still have one remaining partner. Yesterday that person was worth their weight in gold. A problem shared is often a problem halved, and it was in this case.

Entrepreneurship is lonely. If you have a partner you also give up a share of the business, so I am not saying everyone should take one on. As a business grows, though, there is a point where having someone to sit down with and work through the list is worth the split. If you do not have a partner, find someone you trust who will go through the plan with you. Saying the problems aloud and putting them in order helped me as much as the spreadsheet did.

What I would suggest if you feel the same

If you are dealing with entrepreneurial anxiety or overwhelm, these are the steps I followed:

First, write down every issue. Get them out of your head and onto one page.

Second, run each one through a problem-solving framework. Reframe it, list what you control, make a plan for those parts and remove the emotion.

Third, put the actions on a timeline with milestones, so you can see what happens this week and what waits.

Fourth, add the cost and the date to each item, and check the cashflow effect before you commit.

Fifth, move things around until the plan is realistic. A plan you cannot deliver adds to the pressure instead of removing it.

Sixth, speak to someone. A partner, a mentor, a friend who understands your business.

None of this removes the work. It gives the work a shape.

How this connects to the mission

I run every day as part of an attempt to cover 40,075km, a lap of the world, and to raise £1M for children's causes, including Great Ormond Street and BBC Children in Need. I have now covered 16,059.56km, which leaves 24,015.44km. I am building towards a 16.5 year streak, and that length of time means I will have many bad days in business as well as on the road. I will not avoid them. What I can do is have a method ready for them.

Children's causes are the reason the method matters. The mission needs me to keep going for years, which means protecting my health, my mental wellbeing and my businesses along the way. Overwhelm that goes unchecked puts all three at risk. A plan is one of the most practical ways I know to protect them.

Today's lesson for me is a simple one. When things pile up, I should not wait to feel ready. I should open the plan, put the problems on it, attach the money and the dates, and let the picture settle before I decide anything else.

If this episode is useful to you, the full vlog is on the channel. Subscribe, share or leave a comment. The more people the mission reaches, the more we can raise for children's causes. I will be back out running tomorrow.

Watch the full episode: https://youtu.be/IKlLMPhzO4U

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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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