You can only connect the dots looking backwards
My last article was about failure and fear, about how the only real failure is not trying. This week, I want to talk about what happens when we DO try, and it doesn't go according to plan.
Last week, I spoke to two intelligent, well-educated young women in their late 20s and early 30s. Both wondering what to do next, both afraid to make a mistake, and both wanting to figure out "the thing" - the right path, the right choice, the one that will make sense (for the rest of their lives).
We know the world and work have changed. Our lives are getting longer. The world is unpredictable. Yet somehow, somewhere, many of us still follow unconscious and deeply ingrained scripts - that we should figure it all out, ideally for life. That we should map it all out in advance. That making the "wrong choice" means defeat.
The fear is strong - fear of making a move, a change, and fear of it all not working out the way we thought it should. Fear of having to admit we chose wrong.
Steve Jobs summed it up perfectly in his Stanford commencement speech: "You can't connect the dots looking forward - you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future."
I understand that fear because I have been there too. I was a big planner and, at times, almost a control freak. At 23, I had the "perfect" career path mapped out… None of it went according to plan - not the job, not the city, not the career trajectory I imagined.
And I am sure you have your own examples as well, perhaps more challenging than the ones I faced.
Because that is life - it often does not go according to (our) plans. It is filled with ups and downs, the good and the less good, and sometimes with very bad. And it has this habit of throwing us a curveball when we least expect it!
At the moment of happening, it often makes zero sense. But looking backwards, we can see the patterns that are simply impossible to see when things are taking place.
Why does it make no sense at the time?
Why does it happen? Why to us? Why, when things were starting to take off, or were going so well, or seemed to get better?
This comes down to our human nature - disliking change and wanting things to stay the same when they are good. Or what we perceive as good for us at that very moment.
Over life and especially looking backwards - which is the title and the theme of this article - I have come to learn that things indeed do happen for a reason. Only a reason might not be immediately obvious to us, especially not at the moment it happens.
The job we were fired from
That job we were fired from? In most cases, if we are actually honest with ourselves - which is not easy in itself - we will admit that we were not particularly happy in that one workplace.
Yes, perhaps it was a mass redundancy (which unfortunately happens these days at an increasing rate). And maybe the entire thing caught us fully by surprise.
I will dare to say, though, that more often than not, this is not the case.
What seems bad at first might turn out to be the best thing in our lives. Because it pushes us further, to do what we thought about, and dreamed about - but did not dare to try because we chose to stay in our comfort zone. When someone or something else decided for us - a decision we might have even wished for but were not ready to admit, even to ourselves.
Maybe for you, it was a project that didn't get funded. A promotion that went to someone else. A partnership that ran its course. Whatever it was - can you see now, looking back, what it made space for? What new direction does it open?
The move that changed everything
Moving to Munich, where I knew no one, just to end up without a boyfriend two weeks before COVID hit. At the time, it felt like literally everything was falling apart.
But it sent me on my big self-discovery journey of understanding my own relationship patterns and choices. It allowed time (forced it, really) to figure out what I want and need, to admit to myself some hard truths. And only then was I ready to meet my husband.
Today, I am incredibly grateful for it all. For the lows and the downs, the tough times and disappointments, and for all the things that did not go as per my plan, because life really had a better one for me.
Telling me that at the time of happening would have just pissed me off. But we can only connect the dots looking backwards, can't we?
Maybe for you, it wasn't a breakup during lockdown. Maybe it was a relocation that didn't go as planned. A relationship that ended differently than you hoped. A chapter of life that closed before you felt ready for it. Whatever it was - what door did it open that you couldn't see at the time?
Life has ways of proving us wrong
As David Epstein writes in Range: the most successful people often have the most winding paths. What looks like failure or distraction from the outside is often exactly the experience that prepares them for what comes next.
Case in point: At 17, leaving Serbia for university, I swore I'd never touch the German language again. My least favorite subject - I was done with it.
Twenty years later? I live in Germany, married to a German, and speak that very language every single day. And I enjoy it!
Life indeed has its ways of proving us spectacularly wrong.
What second-time founders know
We have all heard that second-time founders do better than first-time founders. It makes sense - they have likely learned from mistakes the first time around and hopefully do not repeat them.
But here is what is interesting: most start their second companies in completely different industries and sectors. So it is not just about the specific learnings they carry forward.
What seems to happen is that they have more confidence after the first time. After having dared and "failed" to achieve the desired outcome. When we try, and it does not work out, especially as time goes by and the initial disappointment subsides, what stays is the fulfillment of having tried. For having dared, for our own courage. And for being a person who has the courage, which in turn informs our sense of self-worth and confidence.
This is what the two intelligent young women I spoke with are missing. Not a perfect plan. Not a certainty about the right path. But the confidence that comes from trying, from making moves, and from trusting they will figure it out as they go.
Questions to help you connect the dots
So how do we actually do this? How do we connect the dots when we are standing in the middle of uncertainty?
By looking backwards: What experience from your past seemed like a setback at the time but prepared you for where you are now? What did it teach you that you needed to know?
By looking around: What in your current situation feels difficult or unclear - and what might it be teaching you that you will need later?
By looking forward: Instead of asking "What is the right path?", ask "What is the next step I can take without needing to know the entire path?"
Herminia Ibarra's research on career transitions shows that we don't figure out our next move by thinking harder. We figure it out by trying things, by experimenting. The path reveals itself as we walk it - not before.
What I know now, and what I wish I could tell my 23-year-old self planning the "perfect" career path, is that the detours matter. Unexpected turns matter, and plans that don't work out matter too. Not in spite of being unplanned, but because they are unplanned.
They indeed teach us what we cannot learn any other way, take us places we would never have chosen, but turn out to be exactly where we need to be. And they prepare us for opportunities we cannot yet see.
Questions to ask yourself
So I want to leave you with a few questions:
What in your life right now feels like it is not going according to plan?
What past "detour" are you now grateful for?
If you looked at your current situation from 10 years in the future, what might you see differently?
What step could you take today - without having to know where it leads?
So if you are standing where those two young women are - trying to figure out the perfect path, afraid to make the wrong choice, wanting certainty before you move - let yourself off the hook. You cannot connect the dots looking forward. You can only do it looking backwards.
Take the next step. Trust that it will make sense later, even if it does not make sense now. Trust that the dots will connect, even if you cannot see how yet.
Because looking back, they always do.
I will finish with a beautiful quote by Lao Tzu: "A journey of a thousand miles begins with a single step."