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How to plan the next chapter of your career story


DATE: 17 July, 2018

Almost everyone I spoke to in the run up to the end of the year told the same story: “So tired.” “Beyond exhausted.” “Can't wait for this year to be done.”

I was in the same boat, lashed to the mast and hoping the storm would blow itself out. To quote a popular philosopher from an era when the music was, quite simply, so much better (trust me on this, kids), I'd lost my ignorance and didn't know where to find it. I'd even lost my sense of humour. For those who know me, that's like having 90% of my personality deactivated.

In short, last year happened to me. In the few gloriously lazy, hammock-swinging days since then, I've made a decision to ensure this year doesn't do the same. And I think I know how to do it.

Your life is a story, great stories follow a plot

As some of you may know (What? You don't know? I thought I told everybody. At least twice), I fulfilled a long-held ambition in 2017 by publishing my debut novel – a fast, fun satire of startup culture and digital nomads.

ShelfLife' took a long time to write, mainly because I didn't plan, I thought I could just keep writing it and it would somehow ‘turn out'. That approach meant I wrote the manuscript maybe two and a half times before realising that I'm much more effective as a ‘structural writer'. Structural writers have a plan, but they have also something else.

Great writers start at the end

Deciding what your 2018 is going to be like is similar to writing a story – hard to know where to begin if you don't have a clear idea of how it's going to end.

And that's the ‘main takeout' of this piece.

If you want to be a bit more intentional about where the next chapter of your career is going to take you, here's my advice:

Forget the list: what do you want the end of the year to feel like?

Many people confuse a plan with a set of actions. It's also tempting to start listing things, as it feels more technical, more solid.

We've also been trained, by a bazillion blog posts just like this one, that lists are both important and efficient.

Moving away from the ‘To Do' list of activities instantly gives your goal more clarity and purpose. For example, saying you want to feel like a leader is better than saying you need to double your staff. Ditching the list also gives you way more freedom and flexibility to find your own ‘hero's journey' as 2018's antagonists throw obstacles and plot twists at you.

Plan to have a plan

It's a crucial first step, but one that's often missed. Set aside some time to make your plan. Book a meeting with yourself. Go for a lunch. Take a walk with a friend. Can't find a friend? Go for a walk with a voice recorder.

The point here is to recognise that having a shopping list is not the same thing as having a well-stocked fridge. Make sure you give yourself time to go to the shops.

Pick the first thing you can do and the first day you can do it by

While I admire the work ethic of people who complete NaNoWriMo, very few great books get slammed out in a single burst of frenetic activity. The gargantuan size of the task of planning your life (Oh. My. God.) often overwhelms people.

So how do you get started? Break the big thing (become a coder by the end of the year) down to a small step (investigate courses and make a shortlist) with a deadline (enrol by the end of the month). The next small thing will then become apparent. Go and do that thing. Rinse and repeat.

Plan on several fronts

This is essentially a career and creativity blog, so you're probably thinking more about that part of your life right now. Life, like the best stories, is way more interconnected than that. My recommendation is to keep going.

Plan for what you want to feel at work, home, when you travel, while you're relaxing, pursuing your passion project (are we still calling that a ‘side hustle' in 2018?) and, crucially, when you're with the people you love.

You may find some parts of these plans are similar, making them easier and more fulfilling to go after. Some plans might be diametrically opposed (crushing your startup while increasing your hammock time, for example). Press pause on the planning and make some decisions.

Practice what you blog

Me? I've got plans happening on several fronts right now. On the home front, we spent last year doing a financial plan, so this year we plan to feel like we're being decisive.

On the travel front, we've got some significant birthdays and anniversaries coming at us, so we're planning to feel excited and joyful.

On the work front, we've had a solid year of honing our team and crafting our reputation, so this year we plan to carve out a couple of unassailable niches.

And on the writing front, I've discovered that your first novel is just the start (if you really want to be a writer), so I'm planning the structure of my follow-up, tentatively titled ‘The Stacking Plan.'

And you? What's the plan for your career story?