3 min read

I thought I lost my WHY

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Over the last couple of months, I've had a hell of a time. In short: a trusted advisor and financial influence in my business turned out to be a scheming predator. I had to confront some ugly truths about the advice I'd been given and the situation I was in, and it was messy.

At pace, my dreams for the year fell apart. Stabilising my business took priority (while I neatly compartmentalised the assault that had blown the whole thing open into an emotional zone for future processing...) Not great. There's a long piece in that one, when I'm ready to share, but for now, let's look at the business stuff.

Almost overnight, I went from accelerating my little enterprise into a big booming business, set to take on the world, with staff and assets aplenty... to winding the whole thing into a different little shape as I picked up the pieces. Yikes.

Luckily, I'm good in a crisis. It's my number one skill. The fallout was bumpy, and I didn't manage it perfectly, but I did manage it. What I didn't see coming was the impact on my ambitions. When the initial adrenaline rush was over, I found myself floating aimlessly and unanchored, untethered to a concrete goal for the first time in my life.

Before things blew up, I had a tidy business plan for the next few years. Revenue targets, growth plans and client development. IP. Strategic projects. Everything was nicely mapped and I knew exactly what I was focusing on.

With that scaffolding gone, I became rattled. I was still doing all the things - workshops, meetings, training sessions, admin. But without the big goal to hook that activity to, I wasn't sure how to feel about it anymore.

After a few weeks of going through the motions, I spent long enough in-situ in my office, contemplating the physical reminder of the disarray, that I was forced to start thinking it all through.

Had I lost my why? Without my growth agenda and revenue targets, without a big team, had I lost all of my goals?

I spent a bit of time feeling sorry for myself and licking my wounds, before I ate my own dog food. The most useful framework I use with clients and students, by a country mile, is my Strategy 101 diagram - the Why, How and What of strategy. It applies in more contexts than I can shake a stick at, and I'm always drawing on it.

This situation is no exception. A big business is not a why. A revenue target is not a why. Those things are hows, at best. There are better questions that need examining here: why did I want that in the first place? What need was I trying to meet? What fear was I trying to quell? What values was I trying to animate with action?

It's those things I've been sitting in for the last little while. The truth is - my why hasn't changed, my how has. A business model is a how. A strategy is a how. A job is a how. And the how I'd chosen was wrong, for all kinds of reasons:

  • A lack of readiness (I moved too fast)
  • Misalignment with my broader values (By stepping back from delivery, I lost connection to my clients and the meaning of my work)
  • Capability mismatch (I hate managing a large team!)
  • Scope issues (I built the behemoth, not the MVP)
  • Gut check (It didn't pass, but I proceeded anyway)
  • External influence (I was too influenced by the advice of someone who had no skin in the game)

Along with the typical personal stuff that gets in the way at work - rush, greed, panic, ego et al.

But the main reason it was wrong, is because I wasn't walking the talk on the essence of strategy: I wasn't trying to work out how best to move toward the outcomes I care about most. I was retrofitting possible outcomes onto an exciting opportunity, like a square peg in a round hole. That's what we do, when we really want something - even when it isn't right. You might be able to think of a time you've done that too, and even a time where you've come to regret it later.

There's no tidy end to this story, not yet. Whys don't always pop up when you need them, especially if you've lost your way. Working out the essence of what you really care about, and being clear about how that will shape your life requires time, space and care.

I'm going on a journey over the next little while, where I try a few different prompts to reconnect to that why. I'm planning to answer a different question every day, for the next couple of weeks.

They'll include prompts like:

  • What's missing from my life?
  • What is the worst thing I could imagine?
  • When have I felt best about the work I'm doing, and what were the ingredients of those experiences?
  • What are my most important values?
  • What do other people seem to care about, that I don't?

The idea is that after some serious thinking, chatting, and jotting, I'll come to a clearer place. 

I'd love you to come on that journey with me.

If you're feeling a little like you've lost your way too, or you're just curious to see how it pans out, feel free to sign up to my Question A Day experiment.

For the next couple of weeks, I'll send you a new question or prompt to contemplate, every day. You can do what you like with them - journal, chat to your partner, or raise it with your team. You don't need to share it with me, or anyone else for that matter. I may share some of my answers as I go, or I may not. We'll see.

Update: the Find Your Why experiment has finished - but you can check out the progress, including all ten questions we answered here.


Watch the Strategy 101 Video here: