My Tactical Getting Unstuck Kit

Here's what helps me get going when I'm stuck.
My Tactical Getting Unstuck Kit

Note: this article isn't quite finished yet. Give me a few days, haha!

Another note from 8 months later: I never truly finished it! Oh well.

When was the last time you felt overwhelmed by the task at hand to the point of quitting it altogether?

Perhaps you keep thinking about starting something, but never doing it?


Happens to the best of us.

Sometimes I struggle with my writing. Leveling up my product management skills gets complicated at times. Swimming drills with a coach are often a pain. And don't get me started on my entrepreneurial experience!

It's easy to get stuck overthinking, overanalyzing, worrying about the consequences, or simply not knowing how to resolve a particular challenge.

That's when my Tactical Getting Unstuck Kit comes to the rescue. It's a set of helpful questions and assertions I use to get myself unstuck and moving.

Here they are:

  • You're overthinking it.
  • It's good enough.
  • No one cares.
  • What's the worst thing that can happen if I do it? What if I don't?
  • So what?
  • What's the smallest next (first) step I can take?
  • Just do it.

Here's how I think about them:

You're overthinking it

This is one of my most powerful and most helpful assertions.

It's also the one that's very often true. When I'm stuck on a particular task, it's usually because I'm overthinking it.

There are a few different reasons I can be overthinking:

  • The task at hand is too vague, and I'm trying to clear it up.
  • There are multiple ways I can proceed, and I'm trying to calculate the best possible one.
  • I'm trying to protect my downside by minimizing the risk.

All of these are valid issues. Our brains don't like working on unclear projects, vague goals, and ambiguous tasks with multiple possible implementation options. And rushing to do something without considering the consequences isn't a great idea even if what you're doing doesn't involve the risk of death. Doing without thinking is the opposite of being strategic, and being strategic is how you succeed in the long run.

However, overthinking isn't the same as thinking. It's worrying about the same things repeatedly to the point where you become paralyzed and unable to make a decision or take action. Overthinking makes projects and tasks more vague, not less. It mentally magnifies the severity of consequences. And instead of minimizing risk by picking the best possible move you end up not making the move at all, forgetting that not taking action is a risk in itself. Failure to act.

Here are just a few recent examples of me overthinking:

  • Abandoning the essay I'm writing because it's not good enough and I'm a fraud.
  • Failing to apply for a job because my CV isn't quite perfect yet.
  • Taking a week to record a simple video testimonial because I'm self-conscious on camera.

These are all trivial examples, but that doesn't fend off overthinking. When you're working on something that isn't quite clear-cut, it's easy to lose perspective. And losing perspective is the fastest way towards overthinking.

In my case, simply becoming aware of me overthinking is often enough to stop it. "You're overthinking it, man" is one of my best friends when it comes to battling perfectionism and procrastination.

It's good enough

I'm not normally a perfectionist, but perfectionism often strikes me when I'm deep in the weeds of working on a particular task.

This is often the case with more creative work, such as writing, recording videos, or things like devising a strategy, which I consider a creative process. When I'm genuinely engaged in something, I tend to look at the results with a more critical eye than I usually do, without considering the bigger picture and the law of diminishing returns:

  • "I can make this essay better if only I do another editing pass (or five)."
  • "I don't really like the way I said this word toward the end of my video, let me re-record it."
  • "This email I'm writing could use a little more personal touch, I think I'll send it later."

Again, trivial examples.

Two common consequences of this perfectionist mindset in my case are:

  • It takes me more time to finish the task with little difference in result.
  • I keep postponing work on the task, which makes it sit at the back of my mind, worrying about it, and sometimes abandoning it altogether.

This is how I almost abandoned the idea of starting this blog because I didn't like what my first essay looked like. It's also something product creators and solopreneurs struggle with, working towards the product launch, but never actually launching.

If overthinking mostly wastes your mental energy (not great), perfectionism also wastes your physical energy.

And just like with overthinking, it's often enough to simply become aware of that fact that I'm perfectionizing to snap out of it. Not a very scientific approach, but "It's good enough, man" has many a time saved me from wasting my time trying to perfect the things that are in fact good enough already.

No one cares

Worrying about what other people think of you can easily mess up your life.

In the worst case scenario, you develop a crippling social anxiety and shut yourself out of the world altogether. But it doesn't have to be that bad to have a detrimental effect on your life. You might be tempted not to speak out. Not to write in public. Or just not be yourself in public, and go about your life wearing a mask that hides the real you.

I went through all of this. Getting bullied in school made me clam up for years and avoid interacting with people altogether. Starting and shutting down a business and going through two identity crises helped me overcome the worst aspects of this, but I'm still occasionally self-conscious when it comes to putting myself out there.

And if there's anything I learned from this whole experience it's that putting myself out there is what really makes magic happen. It's how you meet new people, visit new places, encounter new opportunities. It's how you create serendipity.

The other thing I learned? People don't really care about you, in most cases. You're an extra in someone else's movie. Everyone has their own lives to live and their own challenges to overcome. Not doing something because of what others might think of you is essentially not doing something for no valid reason.

When I have to put myself out there, I that's what I like to remind myself of.

What's the worst thing that can happen if I do it? What if I don't?

But what if someone does care? What if they don't like me? What if something goes wrong? What if everything goes wrong?

You can't not think about the possible risks at all. But just like thinking is different from overthinking, assessing risks is different from catastrophizing. That's when you assume the worst will happen without having the reasons to do so.

I used to do that a lot in my 20s:

If I fail that job interview, I'll never get invited to another one again and will die penniless. If I ask my question during this meeting, everyone will think I'm stupid, and I'll get fired. If I share my thoughts online, people will disagree, and they'll hate me. If I send this cold email, I'll get called out in front of everyone for being annoying.

In practice, none of this usually ends up being true. I've failed more interviews than I can count, and I still ended up getting that job. I've never gotten fired over a question, even if it wasn't the best one. I'm sharing my thoughts online right now, and while not everyone agrees with me, it's not the end of the world.

In fact, just like with overthinking, not acting due to the irrational fear of something bad happening will often (usually?) result in a worse outcome. Not asking questions prevents you from learning and improving, which may get you fired. Not sharing your thoughts with those around you robs you of opportunities.

It may even get you killed. I remember that one day early into my skydiving hobby when I forgot how to arm the automatic activation device, and was reluctant to ask the people around me because I was afraid they'll think I'm dumb. I did ask eventually some 10 minutes before departure. Super embarrassing, but what's the worst thing that could have happened if I hadn't?

So when you're reluctant to act due to the fear of something bad happening, ask yourself: "What's the worst thing that can happen?". I guarantee that in most cases, the answer to this question won't be too far from "nothing, really".

So what?

If the objectively worst possible outcome isn't "nothing",  I use "So what?" question to assess the severity of the possible consequences.

A few examples:

  • TBD

What's the smallest next (first) step I can take?

This is a good one that helps me turn vague tasks into more specific ones.

When I struggle to start or continue doing something, it's often because I don't have a clear next step. Asking myself this question is an easy way to clear this up.

I've found that quite often a good next (first) step is "do the initial research". I like to use checklists in Evernote to break things up a bit, and many of my larger projects start with "do the initial research" and "outline the next steps". These aren't the most specific steps, but they're often enough to get me going in the right direction. And once I get going and researching, the next steps are a lot more clear.

There are a few different ways I use to define my next steps:

  • Task-based ("do X task")
  • Time-based ("do X for Y minutes")
  • Volume-based ("do X for Y reps/words/whatever")

Sometimes I use James Clear's 2-minute rule and do something for a very brief period of time just to get started. This makes it easier to keep going.

What's the simplest way to get this done?

I usually ask this question after I catch myself overthinking or perfectionizing repeatedly. It helps me get to "good enough" ASAP, and move on.

If you're in the startup or product world, this is not unlike building the minimum viable product and getting it to market. It's also what many first-time solopreneurs struggle with. The first time I decided to start a software marketplace business I spent a few months just thinking about the architecture and the technology, then a few more building it. It flopped. I could've saved myself months of time and embarrassment using a ready-made solution to quickly disprove my assumptions.

Remembering this and some other personal experiences, I made sure not to spend more than a few days setting up this blog. And I could've done it faster, but I wanted to tweak the template to simplify the UX even further. I look the same at other things now. Will add a few thoughts later.

Just do it

Just imagine that Shia LaBeouf gif and go do it.

It will be alright in the end

And one more thing. Staying optimistic helps a lot!

Two of my favorite quotes come to mind:

  • Everything will be okay in the end. If it's not okay, it's not the end.
  • Everything is figureoutable.

I've embraced determined optimism after going through my second identity crisis. For a few months, I was waking up with a feeling of despair and hopelessness. It felt like nothing I did mattered. It wasn't great, but I got through it.

Since then, I'm trying to stay conscious of the fact that life just sucks sometimes. But there's no reason it will always stay this way. No matter how bad things look right now, there's no reason they will always stay this way. It gets better.

So let me end this with a short pep talk:

You will figure it out.

It will be alright.

I believe in you.