A year of wandering, and wondering — a year in career transition

Jimmy McLoughlin
8 min readOct 19, 2020

This post is a summary of what I have been up to since leaving №10 a year ago, how I am now going to try and help with the employment challenge coming up and a call to action for how you can help.

When I left Downing Street a year ago, having been a business advisor to the Prime Minister, I was embarking not just on career change. I was facing one of life’s biggest adventures, becoming a dad. We were expecting our first child in September 2019, and that was my main focus as I walked out of that famous black door for the last time.

Becoming a parent I knew would be a big challenge, but when it came to the next steps in my career, I just thought I needed a bit of headspace after a few high octane years. One of my responsibilities had been to advise the Prime Minister on entrepreneurship and technology, or the ‘future economy’. Therefore I thought, given time I’d be able to work my own next career steps out.

Boy, oh, boy did I call that spectacularly wrong.

Now admittedly, after returning from a few months studying in California, I had not predicted a global pandemic would intrude as dramatically as it has in all of our lives. My wife,returned to work in the NHS after just a few months of maternity leave as the country was plunged into lockdown, the phrase ‘left holding the baby’ took on a very literal meaning. While this wasn’t the original plan, it has been a wonderful experience, and gave me more time to think about the world our child is growing up into.

The process of figuring out what to do next

Working out what to do post №10 was and is hard. You have been at the centre of government and on occasion wielded significant levels of influence (at other times you feel about as influential as a man shouting into a hurricane — but perhaps I should not dispel the illusion of the all-powerful SpAd).

I wanted to do something which ideally:

  • had a social impact at a similar scale
  • was interesting
  • was enjoyable (they are different)
  • involved working with people that I could learn from and a team that i could develop
  • used my knowledge of politics and government — but not solely that
  • Gave me a chance to work with both start-ups and corporates
  • Flexibility to look after my daughter

I’d not be honest if I said money didn’t matter, you can have all the purpose and impact in the world, but only the privileged few can afford to do it for free.

Was all this really too much to ask?

You can tell that I started without a very clear plan. Jeff Bezos refers to this as ‘wandering’, a highly inefficient process, guided by gut, intuition, and a deep conviction that the prize at the end is worth the messy route to getting there.

The Last Year

Over the last 12 months, I have been fortunate to receive some wonderful, and candid, counsel and advice from business leaders. I thought when I moved on from Downing Street that people would be less interested: I was well aware that people were speaking to me as ‘Jimmy from №10’, not just in my own brilliant self.

I was too cynical. I have been surprised by the amount of people who have offered to help out. They have found time to dispense their counsel — their guidance has been superb and I have been lucky to have it.

The so called ‘lightbulb moment’

As I have been on this long search, I have had this nagging thought that, if I am finding this all so difficult, even with the benefit of the contacts I have accumulated, how would someone who doesn’t have that good fortune go about making a major career change?

So through this not-very-structured process, it became clear that helping people navigate this confusing territory was actually what I wanted to do. Mentoring exists, but what grabbed me was the question, could it be done at scale? And could do it be done in a light-hearted and approachable way?

That is when a lightbulb lit up in my head.

Well, in reality it was more like one of those old fluorescent ceiling lights that flickers several times before it actually turns on properly.

Could I effectively reproduce the briefings that I used for the Prime Minister on the future of business, but put it out there for more people to benefit from.

And that is where the idea for the podcast came from, which I’m calling ‘Jimmy’s Jobs of the Future’.

You can listen to online over at Buzzsprout

On Apple here

On Spotify here

Make sure you subscribe and then you won’t miss an episode.

The premise is simple:

I am going to sit down with entrepreneurs building businesses and ask them ‘where do you think the jobs of the future will come from? And how can people ready themselves for it?

The truth is no-one knows what the future holds, but speaking to entrepreneurs who in some cases are literally building the future, seems a good place to start.

Where does Hayden Wood from Bulb, which was founded five years ago, employs 900 people and is the fastest growing private company in the UK, think he is going to be hiring for in 3–5 years time? Where is he short of skills right now? What do the fabled green jobs of the future actually look like?

It was one of my responsibilities to sit with these business leaders when in Government and talk about everything from the apprenticeship levy, stock market listings and of course their concerns about the latest round of Brexit negotiations. This podcast will just focus on jobs though.

I hope it will be useful for those starting out on their careers, those transitioning and even those who are a bit longer in the tooth.

The Name — Jimmy’s Jobs of the Future

A word on the name, I had originally called the podcast ‘careers counsel’, but both Pip Jamieson and Kathryn Parsons said, ‘brilliant and timely idea, really boring name’.

Pip even went as far to say, ‘I’ve actually forgotten the name already and you only said it two minutes ago — that’s how forgettable it is’.

I told you they can be candid.

It feels slightly (ok, very) narcissistic to put one’s own name in the headline, but it needs to be easy for people to search and sound catchy — Jimmy’s Jobs of the future I hope will achieve that.

The pilot series of Jimmy’s jobs of the future

Some of the guests include Kathryn Parsons of Decoded, Pip Jamieson of the Dots, Hayden Wood from Bulb and Sarah Wood of Unruly.

It will be 8–10 episodes, with one released a week in the run up to Christmas. If it is a success, I will look into a second series in 2021. I am boot strapping it, I’ve just paid for a bit of editing, and an album artwork piece.

I am continuing to work on other projects in the skills and education space, such as FORTE Financing of Return to Employment, a company which is run by a brilliant entrepreneur, Nat Ware, which has an innovative way for how we can leverage more money into retraining people, allowing people to use their future tax receipts to fund upskilling programmes. Whilst also sitting on a few advisory boards at Zero Gravity and Foundervine.

How you can help Jimmy’s jobs of the future?

Starting any new venture is daunting and requires a certain awareness of the vulnerability you are putting yourself out there, I have not done broadcast interviewing before, so it will be a bit rough and ready in parts. It will be a success if I can get into peoples ears who might not expect it. They’re the people I really want to reach.

Therefore, please support us on social media, in particular on LinkedIn, as I think people looking for jobs will be spending time, so please post us there. Our LinkedIn page is here. But we will be on Insta and Twitter too — @jimmysjobs

If you want to stay updated, you can subscribe to the newsletter, which will include my summary notes, it won’t be more than once every couple of weeks as a new podcast drops. That is available here.

When it launches could you leave a review and give it a rating.

Any feedback on concept, style and guests is more than welcome.

The Oscars bit — a long list of thank yous

Thank you to the following for their counsel over the last year.

Bruce Mcfarlane, Roger Carr, Sarah Wood, Saul Klein, Brent Hoberman, Alex DePledge, Debbie Wosskow, Herman, Hayden Wood, Amit Gudka, Dan Korski, Alex de Carvalho, Steve Varley, Steve Wilkinson, Stan Bolland, Graeme Malcolm, Jayne-Anne Gadhia, Helena Morrissey, Nigel Wilson, William Vereker, Euan Blair, Sherry Coutu, James Wise, Tim Bunting, Nick Hungerford, Nick Owen, Andy Higginson, Priya Gupta, Karan Bilimoria, Oli Barrett, Nick Jenkins, Ben Francis, Simon Collins, Nick Owen, Sharan Parischa, James Timpson, Richard Walker, Simon Walker, Sophia Bendz, Ben Scott Robinson, Claudia Harris, Christine Hodgson, Duncan Cheatle, Neil Alexander, Henry De Zoete, Jonny Bourfarhat, Michael Hayman, Stuart Marks, Reshma Sohoni, Carlos Espinal, Emma Jones, Tom Brooks, Peter Dowds, Michael Hayman, Mike Perls, Ali Parsa, George Davies, Demis Hassabis, John Bishop, Cindy Rose, Al Lukies, Ronan Harris, Tom Blomfield, Eileen Burbidge, Matt Clifford, David Schwimmer, Gerry Grimstone, Tim Luke, Haakon Overli, Tom Hulme, Simon Meanshey, Andrew Bruff, Paul Kirby, Ella Goldner- to name a few, and I know I will have missed some.

Big thanks to Dan Murray Serter, who runs the Secret Leaders podcast, his excellent guide has been a huge crib to me, big thanks Dan. I owe you a drink when we finally meet IRL.

A few Stateside were very helpful when I was out at Stanford too Ellen Levy, Pete Flint, Andy McLoughlin, Matt Glickman, David Homick, Jonathan Levin, Joe White and of course my professor Yossi Feinberg. A big thanks to my Stanford team, Ryanne, Joe, Mahendar, Rob, Damira and Cassie and everyone on the course who pitched in with ideas and feedback, more often than not at the Nuthouse.

The artwork is by George Cleland Dick, he is a student that has had his design placement year thrown out, he is great and you can check his other work out here.

Eline and Filip at Particle6 have helped edit it all, and have been very understanding when dealing with a novice.

Lastly big thanks to my wife and family who have been very supportive throughout all of this. I know you are glad I have something to keep me occupied.

If you made it this far, you can sign up to receive emails every couple of weeks about the latest episodes here.

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Jimmy McLoughlin

Former Special Adviser to UK Prime Minister on business specifically technology & entrepreneurship currently studying at Stanford GSB. Derby County OBE