Why your career is like a meatball sub. (Hint: it’s the messy bit in the middle).
Remember the first day of your career?
Of course you do.
It’s the weirdest day ever.
You’re still a child, basically, but suddenly you’re dressed like a grown-up and someone gives you a laptop and an ID badge and asks your opinion on stuff and you’re allowed to come and go as you please and it’s all just…a LOT.
(Sidebar - anyone remember the movie Big? It was one of my favourites growing up. Essentially gives you an insight to what it would actually be like if a kid was put in an office. Although some of us already know what that’s like from the experience of working with certain colleagues who shall remain nameless).
David Moscow as Josh Baskin in the 1988 movie Big
What emotions do you remember from that period? For me, if I think back (which is hard, as it was a long time ago) I can remember two things:
a constant unhinged fandango between feeling confidence and feeling like a fraud (“I’m about to get found out”)
being completely mind-blown by the fact that money kept magically appearing in my bank account even when I went on vacation (which, having very few responsibilities, I spent accordingly).
And of course, your skills and experience are scarce. You haven’t had time to build up any of the tricks you’ll need to navigate your boss, your company, your industry - it’s enough if you’re able to just get the printer to work without having to ask someone to help you. Again.
But what’s not scarce? What do you have in such abundance that it’s spilling out of your every move?
Motivation.
Early in your career, that’s just how it is. You get excited by stuff that, later on, will become humdrum, or even a thing you dread. Getting invited to that meeting with all the grown-ups. Being asked to send something directly to one of the big bosses. Someone important knowing your name. Nailing a presentation deck you were asked to put together. Getting a little “good job” email from someone you’re intimidated by.
As for the end of your career? Well, most of the time of course, that’s in the future. But in most people’s minds, it’s a tidy end. A destination. A level you want to reach, a location you want to work in. Or even just a vague idea of the assurance of continued evolution and development until you’re ready to call it quits.
So the beginning is easy. You’re just excited. The end (in theory) takes care of itself.
The middle on the other hand? Well that’s the messy bit. And that’s why your career is basically one big meatball sub. Well defined and under control at either extreme. Messy as heck in the middle.
A meatball sub. See that bit in the middle? That’s your career.
Yes, the middle is where things really get tricky. And it can feel like you’re in the fog. Except it’s weird supernatural fog where the compass you’ve been using up to that point suddenly stops working. And it’s all too easy to get lost.
Why?
Well, I think it can be broken down into three main areas:
Your position;
Your identity;
Your skillset.
Let me elaborate.
Your position
Up until the middle of your career, the stakes are, if not low, at least manageable. You have a lot of top cover. The consequences of any mistakes you may (/ will) make are containable by someone with more skill or knowledge than you. You’re still told to think of them as “learning opportunities”.
But as you approach the middle - you’re a few promotions in, the number of people you lead is increasing, your stakeholders are getting more senior - all that starts to change. The pressure to get things right increases. The consequences of mistakes become harder to contain. The stakes become existential (to your career at least) - a big enough slip, and you’ll be looking for a new job.
Your identity
This is typically also a time in your life when a few other things are going on. You may be starting a family. You probably have ageing parents. Your financial responsibilities are increasing. And on top of all these circumstantial factors, you may also be starting to ask yourself bigger questions. Who am I, really? What do I really want? What are my values and what is my purpose?
What felt true early on (“I’m the ambitious one”, “I’m good at fixing things”, “I’m a high achiever”) starts to feel…inadequate. Like an incomplete picture of who you are.
And all of this combines to create what can be a very difficult phase in your life. (These factors, by the way, are also what is very often referred to - reductively - as a “mid-life crisis”, which in my book is one of the most offensive terms out there and needs to be retired).
Your skillset
Here’s something that gets ignored way too often: the skills that got you where you are not the same as the skills that will get you where you want to go. Early on, hard work is essentially enough. Your superiors will notice your effort, and reward it. The further into your career you get, however, the more your impact is measured not by your effort, but by the outcomes you bring about.
This requires a much subtler approach in all areas - nowhere more than in how you lead and direct the resources (by which I mean people) within your particular part of the business. The skills you have to develop are more strategic. More long-term in their outlook. And, where before you could deal in absolutes, the parameters become greyer and greyer. And the thing these new skills have in common is - they can’t really be “trained”. You have to develop them in harmony with your existing skills and experience, which requires a highly personalised approach.
The effects of getting all this wrong can be very visible - losing the job, getting demoted, moved to another, less visible part of the business. But, more painfully, it is also the invisible effects which extract the highest cost:
An increase the amount of second-guessing you do
Amplifying whatever was already there (imposter syndrome, anxiety, stress, etc…)
…and ironically, making you more likely to make the mistakes you are trying to avoid.
Even more ironically, it’s when you reach the upper rungs of the ladder that more support starts being available. Greater flexibility. More agency. More scope for decision-making. And, in most organisations, it is only at the senior executive level that tailored personal and career development opportunities are made available.
My mission with Blazing Pine is to change that.
I believe that a lot of today’s leadership challenges derive from the fact that too many people are left alone to figure things out, right when they need the most support. That is, when they are navigating the messy middle.
Why do I think this? Well it’s a combination of my own personal experience, and that of the majority of my clients (and if anyone can explain to me why I have senior executives whose coaching is being funded by the employer, yet many of my early- and mid-career clients are funding it themselves, then I’d love to hear it).
I want more of the days in the middle to feel like those early days. The ones when you had all that motivation, all that excitement. When every day felt great no matter what, because you were learning something.
Because that’s the only way you get through the messy middle to the other side. The only way to turn that long-term ambition or goal into reality.
In fact, it’s the only way a career makes sense at all.