This year (annual planning, part I)

Are you someone who thinks detailed annual planning, whether entrepreneurial or life-related, is a waste of time? A lot of people would probably say 2020 proved you right. The jokes write themselves.

In December 2019, I was just wrapping up a three-months-turned-six project at Deliveroo. Afterwards, I was planning to travel for two months (India, Spain, skiing in France – I regret nothing) before then figuring out whether to take on another cool startup project, of which there would always be plenty, of course, or to launch something on my own.

So in January and February, I turned down every project opportunity that came my way: Thank you very much, I’d love to help, but I am currently travelling and not available before early March. Not a shade of worry about whether I’d be able to find work in March that could make my samosas taste any worse while watching the sunset in South Goa. A bit carefree, a bit naïve, a bit arrogant, a bit of all of the above. I miss feeling that way.

In March, I returned from the beaches and ski slopes to what was maybe a few days of normality. I was just starting to look around for what was next, when Covid brought every business I was talking to, and a large number I was a fan of, to their knees.

When the same recruiters who wouldn’t stop calling in January were being furloughed in April, I knew that nothing that I had planned for 2020 would be as I imagined it.

For a month, I was in a grip of a worry spiral that involved a lot of denial/cooking/crafting. In April, I finally found the courage to look at the numbers.

After a few hours of playing with different scenarios, a new plan emerged. The runway was extended. The expectations were lowered. It was much less optimistic, but it wasn’t a disaster. I’ve got this, I thought.

By June, I had a deal with FutureLearn to temporarily step in for their Head of Strategy; by July, I was also doing work for a private equity client, helping them to figure out which companies may be worth investing in. Feeling energised, I also launched Tiny CFO. I scrapped the worst-case scenario from my financial plan, grateful, of course, that the worst appeared to be over.

Or so I thought. In September, my boyfriend Toby and I both got Covid in Slovakia when visiting my family and friends who I hadn’t seen for over six months. When we recovered, my grandpa, who I loved very much, got very ill, very suddenly. In a few days, it became clear to me that I was not caring for an ill person, I was caring for a dying one. I’ve never experienced this before – the loss, yes, but not the process. Seeing him fade away before my eyes was the single most heart-breaking thing I’ve been through so far. (Which I’m fully aware is indicative of what a comfortable life I’ve been enjoying for the past 34 years.)

Work, let alone promoting some silly newsletter, was just about the last thing on my mind. I reduced the amount of work to the bare minimum while caretaking and grieving and picked it back up when I could. Not good for the numbers, but very good for my sanity, and being able to do that is another thing to be grateful for.

2020 objectively sucked, and for so many people it sucked a lot more than it sucked for me. If you had a bad one, I’m so sorry. You are strong, and you will get through this.

The irony of trying to plan 2021 after the year we’ve collectively just experienced is not lost on me but, as they say, the only way out is through. The good news is that 2021 is coming.

Let’s make it a good one to the extent possible; maybe even create jobs, re-invigorate decimated industries, give us something to get genuinely excited about.

Next week – 2021 annual planning for your business.

Love and cash flow,


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