Are you self-sabotaging and yet feeling good about it?
It doesn't take much to work against your own goal and be delighted about it.
Dear Ambitious Reader,
Ambition is not enough. Nor is hard work. If anything, over the years, I have seen extremely ambitious and hard-working people failing time and time again. And frustratingly, they tend to do it as predictably as clockwork, despite putting in blood, sweat, and tears.
This Letter is here to unmask the root of all the surprising failures. To call out the silent saboteur and empower you to see through its ruses, and never again fall for its deception.
Seneca once said
If one does not know to which port one is sailing, no wind is favourable.
You may be more familiar with the more recent Lewis Carrol take on the message. When Alice meets the Chesire Cat in Wonderland and asks him for direction, he tells her that unless she knows where she is going, any path will do.
To go from A to B, one must know where B is. Being clear about your destination is a necessary condition. You wouldn’t set off in public transport or your car without knowing where you are going, yet, most of us are perfectly comfortable treating our lives and careers with a certain nonchalence about it.
If anything, you’d call me crazy if I’d challenged you to take the London Underground, at rush hour on a Friday afternoon in July, without a destination. Yet, this is how we treat our lives.
If you don’t have clarity on what you are working towards, then how do you know if you ever get there? How can you maximise your chances of success, if you don’t know what success spells for you?
The burden of lacking clarity is the first mistake many of my coaching clients carry around with them. If you are aware of it, that’s a very strong position to be in. Without clarity, there is no success.
Clarity is not enough
Albeit absolutely necessary and fundamental, clarity is only one part of the puzzle. I know many people who are very clear about where they want to go to, and still self-sabotage.
The remaining piece of the puzzle is the following axiom: no opportunity is objectively a good opportunity.
Whether an opportunity that comes knocking on your door is good or bad is absolutely and unquestionably subjective. What is a brilliant opportunity for you could be a waste of my time. Yet, society has conditioned us to value certain opportunities as if they were objectively great and encourage us to bypass our critical judgment.
Let me illustrate this with an example.
Let’s say that last year, a friend of mine was invited to attend Harvard Law School, with a relocation package, expenses paid, as well as a nice sign-on bonus, to get a degree in criminal law!
Isn’t that amazing?! That’s the kicker. There’s not enough information for us to assess whether it is amazing or not.
Is this a brilliant opportunity? Possibly, but not necessarily.
My friend is fortunately very clear about where they want to take their life and career. For one, they have a young family, with a strong support network around them, and are keen to lean on that network. They have strong roots and like where they live, they can see this as the right place for their kids to grow up. Career-wise, they have been working tirelessly in building a career in corporate finance, and are currently on the fast track to a promotion, which they estimate could land anytime in the next 6 to 12 months.
That context puts the offer from Harvard Law in a very different light. Even though it is a prestigious programme and an offer that many will envy, this actually is a terrible opportunity for them.
This is a terrible opportunity because
they’d need to relocate to a place where they have no support network to help care for the children
they’d step away from their finance career for at least a couple of years to learn a different skillset altogether which may or may not provide tangential value
taking this up now means giving up on a promotion which is within touching distance and they worked relentlessly for
There is no doubt many people would see that deal as a great opportunity, but it isn’t a great opportunity for them in particular. For them, it’s a distraction, a pull in the wrong direction. They’d be foolish to take it up!
Saying no’s hard, but it turns the tide
Oddly enough, were that story true, my friend would have had an excruciatingly hard time turning the opportunity down. It objectively is an attractive opportunity, it comes with a high degree of social proof and validation and conveys a strong message of potential to the outside world.
But none of this matters, because that opportunity would take them further away rather than towards their goal. Yet, in a weird twist, what should be a No Way! Not doing this! is often treated as a Could I somehow make this work?
This is a mistake many would be prone of making and thus perfectly illustrates my point. If my friend was to say yes to the offer, he’d be self-sabotaging himself and he’d be opening the bottle of champagne to celebrate it!
Saying yes to an opportunity that does not align with your clarity is self-sabotage. There’s no two ways about it. If it takes you further from your goal, the only correct answer is a resounding No!
No is one of the most powerful and underrated words in the English language. Saying No to anything keeps your bandwidth for you to say Yes to the right thing.
Every Yes reduces what you have time and resources to do. Every No protects them. We need to become more comfortable not taking opportunities up, even, and especially, the ones that look good.
The wind can only be favourable if it takes me in the direction of the port I want to reach. Life is hard enough as it is, without us adding opposing winds to the picture.
We need to actively flex that muscle, and instead of taking opportunities in isolation, assess them based on A) our clear picture for where we are going, and how this would aid or detract from it and B) what resources we still have available to take this up. Unless we use those lenses, we will find ourselves extremely busy doing work that doesn’t take us forward, I call this active procrastination
Active procrastination kills careers
What I call active procrastination is the mistaken illusion of being productive, of working intensely on the wrong things.
You are actively procrastinating when you are working on a project that is not aligned with where you want to go. It doesn’t matter if it is objectively productive, as in, you create value in some way, if it is not aligned to your clarity, it’s procrastination.
And unlike real procrastination, this version is rather insidious as you don’t realise you are procrastinating. You are procrastinating, but you feel good about yourself, because you are fooling yourself into thinking you are actually being productive.
And because you think you are being productive, you are chuffed about it, you feel good about yourself for putting in the reps and working on moving the needle. But when the needle doesn’t move, you feel lost. You can’t connect the dots on why you aren’t getting to your goal, so you start blaming yourself and your execution or you lose hope or you decide to double down and work twice as hard, because the only explanation was that you were either too lazy or not good enough. And here goes a vicious cycle that you will struggle to snap yourself out of.
I lost count of the number of coachees I worked with that would recognise this pattern. It’s an uncomfortable place to be in. Working tirelessly and not getting the result and not understanding why. But of course, if they don’t work on the right things, they won’t get the results.
Typically, the only way to snap out of it is to either get a big scare, or someone else pointing it out to you. It’s hard to figure it out by yourself, in the eye of the cyclone. And it’s very easy to fall back into it.
I spent years actively procrastinating on my ghostwriting practice. I let that side of my business continue for far too long, and it took me everything I had to decide to kill it off, in favour of my product career and my coaching practice.
Goes to show. Even as someone who specialises in helping people achieve crystal clarity on where they want to go, and how to get there, I still fall for it from time to time. It’s very easy, it’s too easy, to be tempted by the wrong opportunities.
It really doesn’t take much to work against your own interest and at the same time be delighted about it. I recognise it is rather counter-intuitive to think about it that way, but active procrastination is not a contradiction, it’s the dominant way people spend their time.
How can we protect ourselves?
There is no magical phrase to vaccinate yourself against active procrastination. You will fall for it. Several times. There’s no avoiding it.
There are however a few steps you could take to protect yourself.
Clearly spell out what your goal is
Which port are you sailing to, Captain, my Captain? What does success look like for you?
Now, write it down and keep it on your desk. Laminate it even if you have a laminator. Let it be your compass that you check in on periodically.
Check the compass frequently
My personal system demands that I check every Sunday whether I am spending my time in line with that compass. But because I am human and have a life, I’ll check it every two to three weeks more realistically.
As I plan the week ahead and what I want to achieve, I put key tasks to the test through this lens. If it looks like active procrastination, if it smells like active procrastination, and if it sounds like active procrastination, I kill it, and so should you.
There is no shame in killing something off (and even if there is, it may still be worth it)
We need to be ruthless here. There are commitments you may have and that have served you well but no longer do. There are commitments you kept on for years because you never felt enough discomfort to quit it. But maybe you should.
Review your commitments and your ongoing projects, and see which ones you a) shouldn’t have taken up in the first place, and b) no longer serve you.
I spent several years with Toastmasters International, where I learned to take my public speaking to the level it is at now. It served me incredibly well, and I kept the skills to this day, but I haven’t gone to any meeting in over 5 years.
Why? Because when I decided to cut away from it, I had realised it didn’t align with my compass. Sure, I was getting better and better at public speaking, but I no longer had the ambition to be flown around the world to speak. I also had reached enough the skill level I needed for it to be a competitive advantage in the corporate world and I was getting diminishing returns.
In this example, staying with Toastmasters would have been a very active way of procrastinating. I would be investing a lot of my time (to the rhythm of 10 hours a month) that I could redeploy elsewhere that would more directly impact on my goal, which I did.
Likewise, look at projects you have taken up. Should you abandon them? If you can’t, can you sprint it to completion and relieve yourself of the burden? And if you can’t, what’s the price to pay to just abandon it? It is sometimes often better to disappoint someone than be an obstacle to your own success.
The Formula
The antidote to self-sabotage and active procrastination can be summed up by:
Clarity: I know where I am going
Ambition: I am commited to it, and to ensure I am travelling that way
Hard work: Putting in the work
Saying No: Ensuring we direct our energy and resources on the right things
And lo, until you know to which port you are sailing, no boat will get you there, said the Brazilian coach from Yorkshire before complementing, after a short pause….
I would be aligned with my own clarity if I didn’t ask: if you were to share this article with two people? Who are they and why not share Transformative Letter with them?