Monthnotes — June 2023 — Simon Wakeman

Simon Wakeman
3 min readJun 29, 2023

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June was very much a business as usual month after the disruption of my health scare and surgery last month.

I was properly back at work juggling two fractional roles alongside consultancy and coaching clients.

I’m taking a holiday break in a few weeks time, so this month has partly been about transitioning out of one fractional role and making good progress on a couple of consultancy projects which will need finishing up in July.

With the autumn in mind, I’ve been in full-on business development mode too.

Having a pretty open work schedule for mid-September onwards has been a good opportunity to reflect on the first six months as a freelance COO. I’ve worked with a really wide range of clients and on different types of engagements during this time.

That experience has helped me learn more about what I want to be doing later this year — and so I’ve used this to focus my new business pipeline development work much more tightly than I have done before.

Through feedback and reflection, I’ve seen that I offer the most value when I’m working with founders who need a practical, pragmatic and experienced senior leader to help make their visions a reality.

One client described me as “ the one who makes things work properly” and “ someone who gets shit done “. Both those are pretty good descriptions I think.

Another former colleague described me as a “ serious company builder “. I like that as it describes what I do well — do whatever it takes to build and scale organisations, teams and businesses.

Businesses that are at late seed stage or series A are probably where I offer greatest value. That’s the time when the foundations for longer term scaling are laid, where leadership teams need to evolve and when headcount rises rapidly, presenting new and previously unseen challenges.

I’m enjoying working across fractional and consultancy engagements. For the autumn I’m focussing more on interim or fractional opportunities, while still holding some capacity for one-off consultancy projects for the right clients.

Away from work it was good to get back to running and cycling too.

To prove my fitness post-op, I entered a 34 mile ultra in Kent — which happened to be one of the hottest days of the year so far. It was great to be back running and some new eating strategies meant there were no repeats of the digestive issues I experienced on my last ultra.

A friend’s 50th birthday party also provided a real treat mid-month…a last minute drop out from their booked DJ meant an opportunity to get behind the decks for a proper house, nu-disco and Ibiza mix set for 200 guests.

It’s been a long time since I’ve played out live and to that many people. Needless to say I absolutely loved it and the crowd were in a serious party mood so the dancefloor was rammed for the whole 4hr session.

Music this month…

Been loving the old school 90s house sounds this month. This mix was a particular favourite as it captured a lot of memories.

Podcasts this month…

Not been listening to many podcasts this month, but not sure why. Did catch up on a couple of episodes of Bruce Daisley’s Eat Sleep Work Repeat podcast, which always has some useful work-related nuggets.

Reading this month…

I read a book called Dopesick: Dealers, Doctors and the Drug Company that Addicted America this month. It’s a depressing but also very engaging read about drug consumption — both legal and illegal — has affected the US over the past 20 years. Thoroughly recommended.

Cycling this month…

119.1 miles.

Running this month…

70 miles.

Originally published at https://www.simonwakeman.com on June 30, 2023.

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Simon Wakeman

Consultant, fractional COO and non-executive director for scale-up businesses. NED @ National Support Network CIC. Trustee @ Caldecott Foundation.