Build a plan to Stay Ahead

Making sure you learn the New Tricks you need

Taking control of your learning journey, especially in a mid-career moment, can be overwhelming. But it can also be exhilarating.

We are used to putting our learning agenda in the hands of others.

Schools. Universities. Governments. Employers. Gurus.

All of these can be useful sources of learning, and momentum, but there’s simply no substitute for grabbing control of this process for yourself.

Over the last year, we’ve spoken to a galaxy of LookUP experts, who are doing some amazing things in all kinds of fields of business. The single attribute that most defines and unites them is that each puts deep energy into personal learning - and into reflecting on what learning they need to stay ahead of change.

So, this piece is all about helping you to define your Stay Ahead Plan.

It’s about starting to define a living, ever-evolving learning plan, that helps you to stay ahead of change through learning in multiple directions.

Not feeling ready? In that case, we’d recommend starting here.

Ready to learn? Then let’s do it!

(To access the full framework below, you’ll need to be a paid subscriber - but it will only cost £10 for this month)

Let’s get stuck in. Starting with a question…

Most people, most of the time, don’t have an answer to this question.

And that’s fine. It’s perfectly possible to have a healthy relationship with learning, without having a formal plan.

BUT like other things that happen organically, there is a danger that our plans to developing our own learning are…

Too one-dimensional. Because we get stuck in our head that we need to focus on one specific area of opportunity or weakness, rather than taking a step back.

Too non-committal. It’s extremely usual for learning to be a part of people’s list of priorities, but the least solid or prioritised element on that list!

Our aim here is first to help you explore four different dimensions of learning and staying ahead - and then to give you a framework to help you to maintain momentum.

Staying ahead on four dimensions

Staying ahead isn’t just a straight sprint! Here are four different dimensions of the mid-career journey to stay ahead of change.

1. Reconnect and Recombine

As human beings, often driven by furious neuroticism, we tend to obsess with what we can’t do, what we need to do better, what we think other people do better than us.

So, we’ve intentionally decided to start in the opposite place - because to build a plan to stay ahead, you probably need to start by falling back in love with learning itself.

Maybe that means not lurching directly into your areas of greatest discomfort, in the most judgemental environment you can find! Perhaps instead, let’s start with some of those skills and passions that we let slip somewhere back down the road.

Areas where we excelled at school, like art or drama, that never found their way into our short-term, professional path. Sports or activities that made us feel great, but where we never found the right time or the right context to get the most out of them. Things we nailed earlier in our careers, but seniority took us further away.

In these areas, we can find non-judgemental spaces to explore. Feel the instant gratification of being better than we expected, and rapidly improving. This reconnects us with the joy of learning - because it is fundamental about fun, not competition:

“Judgement is a fun killer. In order to judge something, we have to step out of an experience so that we can evaluate it, and when we are out of our present experience, we are obviously not in flow. Even everyday forms of evaluation, such as “liking” things on social media or editing the selfie we just took, count as judgement and encourage self-consciousness—another fun killer—and therefore will destroy that moment’s capacity to be fun. Comparing ourselves to other people is also a form of judgement and is toxic to fun—as the saying goes, “Comparison is the thief of joy.”

Catherine Price, The Power of Fun: How to Feel Alive Again

It can also be a brilliant reminder of how much more multi-dimensional we are as individuals than we may have felt. This can provide an interesting path towards our next stage. Which may not be about finding the new, so much as it is about recombination. This was brilliantly expressed by LookUP friend and expert Nadim Sadek, serial entrepreneur in fields from research, to whisky, to AI:

"If you've got a reasonable number of ingredients kicking around, you can collide them together in almost any format. The decision-making process about which specific collision to dedicate your next five or ten years to is crucial. It's about finding that specific chain reaction which has been unleashed in you and deciding that's the one to follow. This approach allows for creativity and innovation by recombining your interests and experiences in new ways"

2. Sharpen Up

An obvious next step is to look at some areas which are familiar, but where you know you need to raise your game.

These are often not areas that are totally unknown - rather that they are known discomfort zones.

They can become particularly evident if you find yourself in unexpected waters. Sudden, lateral career moves. Role redundancy situations. The ‘back to square one’ feeling of launching your own business.

For a lot of people, these are areas like strategic thinking, network building, personal storytelling (and a lot of these people are drawn to some of LookUP sessions, courses and content, like our work on Personal Brand.)

It can take a lot of courage to address these areas, but it is really inspiring to see people doing it. Because these are areas where there are few shortcuts.

"The world is full of people who are trying to purchase self-confidence, or manufacture it, or who simply posture it. But you can’t fake confidence, you have to earn it. If you ask me, the only way to do that is work. You have to do the work.”

Russ Harris - The Confidence Gap

Perhaps the key area here is to think about context, not just content. Our forthcoming interview with Philip Kingslan John, who runs immersive theatre company Four of Swords, explores this in-depth in the space of public speaking and public performance.

There's definitely a case that you can rehearse a script perfectly in your bedroom, but as soon as you get with other people, it all goes to pot. Finding supportive, non-judgmental forums where you can practice and have dry runs is really useful. When things go wrong, don’t rush it; have confidence in your material and know that you’re probably doing a better job than you think"​​.

3. Know the New

There are some areas where it’s easy to feel intimidated, because it feels like everyone else understands everything, but we don’t.

This is particularly true in areas which are new, or experience extremely rapid change. It’s fair to say the current poster-child here is Generative AI.

We talked in our first piece this month about this area, and that it is easy to be motivated by fear, where what we really need is knowledge, and a sense of control. As encapsulated brilliantly by Lianre Robinson, AI pioneer and LookUP Expert:

"I think it's really important to just remind ourselves that nothing is staying the same, nothing can stay the same. Even if we wanted to dig our heels in and close our eyes, everything is still moving around us. We have to focus on being ahead of that, and setting up the future that we want, rather than just being pushed in a direction because of the fast-paced changes in the world"​​.

Perhaps part of the reason why some of us recoil from better understanding, is that when we feel we are behind the game on something, we want to feel like that game is not important, or that we are not interested in playing it. The reality is that if we are totally honest, this is rarely the case.

“The story idealists sometimes tell of humanity says we're natural seekers of equality. This isn't true. Utopians talk of injustice whilst building new hierarchies and placing themselves at the top. We all do this. It's in our nature.The urge for rank is ineradicable. It's the secret goal of our lives, to win status for ourselves and our game - and gain as much of it over you and you and you as we can. It's how we make meaning. It's how we make identity. It's the worst of us, it's the best of us and it's the inescapable truth of us: for humans, equality will always be the impossible dream.”

― Will Storr, The Status Game: On Human Life and How to Play It: On Social Position and How We Use it

An area like AI does pose a new set of challenges and opportunities for all of us, and a new game we need to play. We can choose any role in that game that we like, but that game needs to be played from a position of strength, and strength comes from knowledge, and experience.

To reach that position, we need to read, to play, to follow, to get involved. And there are an infinite number of different ways to do that - but inactivity is not a strategy.

4. Burst My Bubble

One of the great challenges, perhaps paradoxes of learning, is that because we don’t know what we don’t know, we tend to learn more of what we knew already.

This is the zone of the ‘unknown unknowns’ - where we know there are reaches of understanding and wisdom and perspective that we intrinsically believe will add to our stock of wisdom and joy, but we don’t necessarily know where to find them.

These areas are particularly important, because if we ever find ourselves profoundly unable to stay ahead of change, this is where the change will have come from.

Perhaps, therefore, this is where we need to work hardest, both emotionally and practically, to push against the invisible constraints of our knowledge and understanding.

And in this we have two great weapons, if we choose to grasp them: the power of other people, and the power of randomness.

Kian Bakhtiari, Founder of The People and close friend of LookUP, is perhaps one of the least exposed people we know to the ‘unknown unknowns’ - and that is entirely to do with the communities he engages with.

Where I start with is what are people doing. Our community members, they're not what I would call like, mainstream audiences. They're people on the peripheries of society, doing cool things. But also in a weird way, they don't have much as much to lose. Because when you're in the centre, you have more to lose. And you don't want to risk doing that or starting a new track, or doing a side hustle or doing something that's embarrassing. And I think what's really interesting is by being able to see like what's happening in the community, in that sense, in the kind of social sense, it's not about reinventing or looking at what the trend is, it's actually being able to see what's happening, what's emerging, and where could things go.

Kian Bakhtiari, LookUP Expert

Growing your network in a way that begins to fill some of the unexplored areas of your map should always be a part of your plan to stay ahead, and you can’t just enter like a tourist…if you want to learn from communities, you have to work out what value you can add that will enable you to learn the things you want to learn.

There are other routes too, into the unknown - and sometimes there is nothing better we can do than entering the realm of the random.

By mid-career, we have all developed pretty strong ideas of who we are, what we like, and where our barriers lie. All of which is very reasonable, but makes it all the more important that we remove the fixed idea of ourself, as expressed here in the excellent Range, as David Epstein talks to Herminia Ibarra from London Business School:

“Who do I really want to become?,” their work indicated that it is better to be a scientist of yourself, asking smaller questions that can actually be tested—“Which among my various possible selves should I start to explore now? How can I do that?” Be a flirt with your possible selves. Rather than a grand plan, find experiments that can be undertaken quickly. “Test-and-learn,” Ibarra told me, “not plan-and-implement.”

― David Epstein, Range: Why Generalists Triumph in a Specialized World

Entering the realm of the random needs us to push quite hard, and to get some support. In a world designed to please us, bursting our own bubbles can be pretty difficult! Mechanics like Stack Magazines can be very effective, or you can follow your friends from one activity you love, to one you don’t know. Or, perhaps, the next time you see a TV show, or a book, or an event, that you really don’t fancy, you should just take the dive and do it!

Your Stay Ahead Plan

As we’ve explored these 4 dimensions, we’ve been building a framework for a plan.

Here is the template for you to follow - we’ll give you some prompts to work through it.

1. Defining the areas

The first stage is to look at each of the different areas, and to think through your priorities in each space (knowing that at any time, 1 or 2 things in each space is likely to be the realistic maximum.)

What do I want to Reconnect with?

Where do I need to Sharpen Up?

Where do I need to Know the New?

Where do I need to Burst my Bubble?

Here’s a worked example, from LookUP co-Founder Matthew Hook’s 2024 Stay Ahead Plan…

Reconnect & Recombine. “More and more of my work is creative now, but my creative first love was music and song-writing. Creating time and space to re-learn the guitar and to write songs will elevate my creativity across the board.”

Sharpen Up. “A lot of this year is going to be spend delivering virtual and remote learning sessions. I need to get to the cutting edge of virtual session leadership and facilitation in order to give people a great experience.”

Know the New. “I don’t need to be a world authority on AI, but I absolutely don’t want it to leave me behind. I need to get deeply invested in some practical use cases, and play with the tools so I’m in a position of strength.”

Burst my Bubble. “I want to do more work with charities, and that means both getting to know people who work in those organisations, and having greater empathy for marginalised communities. I need to change my project profile, and volunteer more.”

2. Find the right levers

There’s more than one good way to stay ahead. Any good learning plan is likely to include a mixture of:

• formal learning

• self-guided research and reading

• following relevant experts in the space

• mentorship and partnership

• in-path experimentation

• random or intentional experiences

Overall, you need to have a good and honest understanding of what works best for you, for example as Jo Royce, LookUP Expert, Consultant-Coach and learning expert (former capabilities and learning lead at Google and Unilever) describes here in our upcoming interview:

I think are, we become conditioned to only learn when we're told to do it, or when it's been marked by someone. Schools can be incredible experiences, but the nature of them is kind of sub-ideal for many people. Unfortunately, inadvertently, you lose some of that joy of free learning and kind of creative learning (with a small ‘c’) and self-led learning. So I think I have always sought out learning personally, because I find it hard to put structure to things and I find it hard to follow process. And it really helps me to be to follow a programme that someone else in that kind of context with deep learning has created. For me, that's a great privilege and a great joy to do that.

Jo Royce, LookUP Expert

But the right learning path for you may be different in the different dimensions - or it may be that there are easier places for you to start.

However you build your Stay Ahead Plan, where you want to end up is with a plan that thrills you, rather than intimidates you. It should look like an adventure playground of learning - testing, but joyful.

If you’d like a one-to-one session with us to work through it get in touch - this is a new service we are offering as of this month.

Otherwise, more to follow with our LookUP List next week - and please comment or get in touch with any thoughts.

Until then…LookUP, and Stay Ahead!

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