Why You'll Never Feel Ready to Start (And Why That's Perfect)

Cole McConnell
February 21, 2025
Many of us dream of leaving our 9-5 jobs.
We all follow the standard career trajectory that the majority of society follows.
Go to college, get in debt, graduate, get a job, start earning a comfortable salary, and repeat.
How many of us, though, feel that something’s not quite right?
As if you aren’t fully fulfilled with the work you’re doing. The career path you’re on.
You know you have more potential than this. You know you’re not fully unleashing the untapped talent and ambition within you.
This was exactly the situation I was in.
Comfortable in my day job, but there was something deep down inside me that just had this strong desire to pursue something more ambitious.
I knew I was destined for something greater.
As I went about my day, however, everywhere I looked I was getting this overwhelming feeling that I was not ready to go out and do something on my own.
I’d see successful business owners on Instagram. I’d listen to podcasts hosting founders.
I’d hear about their crazy work ethics and how they’d carry themselves, and feel as if they were just in another league.
Maybe I’m not cut out for this stuff.
I could never work as hard as them. I’m nowhere near as talented as they are.
I’d compare my current skill set with theirs, and get an overwhelming sense that there was still so much I had to learn before I would be in a place where I knew enough to do my own thing.
“Surely I’d need to learn more about sales before I go out on my own.“
“I’m way too awkward on Zoom calls, how would I ever speak to potential customers?”
Society was telling me that building something for myself was out of reach. That it was for the A+ students and the smart kids only. That I should give up and “wait until later” until I give it a shot.
Maybe when I’m older.
Maybe when I ‘felt ready’.
From time to time, I’d still see myself making attempts toward breaking out, toward achieving freedom.
Little glimmers of hope for a dying dream.
I’d listen to something that genuinely inspired me, or see somebody living a life I dreamed of.
It would push me toward actually being intentional about doing something to work towards my ambitious future.
I’d get so fired up. I’d start surrounding myself with all sorts of successful people. I’d listen to motivational speeches and interviews from successful founders, I’d read books and watch YouTube videos on practical tips to get better and improve myself, I’d curate my social media feeds to only be filled with the best of the best.
Not only that, but after I realised I didn’t have the skills necessary to pursue my own dreams, I even conjured up the motivation to start going out and learning the skills I needed.
I started to watch tutorials. I'd buy uDemy courses and write comprehensive notes from them. I listened to practical advice on how to actually improve at specific skills I knew I needed.
But still, after months, after all of that work, I looked at myself and realised I wasn’t a single step closer toward leaving my day job or toward going out and starting this grand plan I’d envisioned so vividly.
No matter what I tried, it wasn’t working.
There was something missing.
Then, finally, I realised what the problem was.
I realised that no matter how much I consumed, no matter how hyped up and inspired I got from the most motivating and successful people on the planet, it was all meaningless unless I took action and created something with it.
I realised I was caught in an endless spiral of feeling like I needed to learn more, going out and completing more courses, watching more videos, learning more tools and languages, only to finish all of those and come back to realise there were still other gaps in my knowledge that I was missing.
I realised that the problem I’d had all along, was that I simply needed to make a start.
All along, the answer was to start building. Start shipping. Start creating something.
That taking action is exponentially more important than knowing where I wanted to head or how I was going to build it.
Iteration over Preparation / The Incredible Value of Stacked Attempts:
You’ll never feel ready.
There will never be a ‘perfect time’ to quit your job and launch a business.
You’ll never be in a position where you know every single skill you need to before making a start.
The solution is to start where you are, with what you have.
There is an invisible form of value that is completely hidden from the human eye that is far more valuable than people realise.
It’s the wisdom that comes from failing over and over, identifying what went wrong, and implementing what you’ve learnt into your next iteration.
The kind of value that only comes from actually doing the thing – not just thinking about it.
Once I came to this realisation, there were 3 main things I knew I’d have to keep in mind for my journey going forward:
Learn on the way.
- Time is extremely valuable.
- Don’t be that guy who wasted 4 months grinding some course on sales or a new programming language, only for 80% of the stuff he learnt to never be put to use.
- Only invest time into learning skills when you actually run into the wall that requires you to know them.
Your first attempt will suck.
- Look at every successful Silicon Valley founder you know.
- How many of them became successful off their first venture? The answer is very few.
- That’s why I’m intentionally pointing out to you now that your first attempt is unlikely to be as amazing as you think it will be, and how incredibly important it is to start now, fail, but keep iterating on each failure.
All you have to do is get back on the horse.
- Every great leader or entrepreneur shares one defining trait – they can fall off the horse 7 times, but they’ve got back on it 8 times.
- Knowing that your first attempt will suck, all you need to do is realise that if you simply keep getting back on the horse, in the long run, there’s no way you can lose.
Everything Around You Is Designed to Keep You Distracted
After coming to my senses and realising that all I needed to do was make a start, I realised an incredibly vital issue in my life.
In almost every aspect of my life, every single day, there was an infinite onslaught of distractions that were bombarding me from every angle.
The closer I looked, the more I realised I was a slave to futile interruptions, preventing me from actually doing the work.
Being able to focus on a single long-term goal and stick to it is a superpower.
The Most Deadly Form of Distraction
Maybe you’re reading this, thinking this is obvious.
Thinking that you’re in a better position than most people you know because you don’t scroll brain rot for 30 minutes each morning and each night before bed.
I was under the same impression.
The reality is that there’s a far more deadly form of distraction. It’s right beneath our noses, and I guarantee you that 98% of all hardworking ambitious people will fall straight for them.
Distractions, in the form of productive tasks.
But Cole, how can a task that’s productive be a distraction?
Think about it.
You sit down to start doing some dedicated work towards your ultimate goal. As you’re sitting there, you remember there were some emails you needed to process, there were some notes you needed to write about an idea, you stumble across a YouTube video that’s genuinely useful and may help you towards your goals.
These activities feel productive, they feel productive because they are productive.
But they don’t move the needle.
They don’t actually help you make real progress toward your overarching goal.
The real progress comes purely from finding your highest lever moving tasks – and completing those above everything else.
If your work isn’t producing tangible results, it’s just a smarter form of procrastination.
Practically Identify Distractions
Here’s how you can take a look at your life, ruthlessly identify what you’re getting distracted by, and take back control of your time.
Time Audit
You’ll think this is stupid. You’ll think this is unnecessary. I’m telling you – it reveals a lot more than you’d realise.
Create a brand new empty Google calendar. For an entire week, document and record what you find yourself doing for every single 30-minute block throughout the day.
When I first did this it amazed me how many blocks I had where I really couldn’t define what exactly I had just done in that 30 minutes. I’d just sort of… existed. I had no tangible output from that time slot.
It’s the perfect way of taking a good hard look at yourself in the mirror, and realising you need to become more intentional with every morsel of time in your day.
Timeboxing
Parkinson’s Law.
If you don’t explicitly define how long you’re going to spend on each task you do, inevitably it’s going to result in your task taking longer than you’d want to complete.
There’s incredible value in pre-planning exactly what main lever moving task you’re going to work on, how long you’re going to spend on it, and exactly what you’re going to move onto next once you’re done.
Doing this prevents scope creep, focusing on things that don’t matter, and forces you to perform at maximum output in the limited time you have available.
Accountability
This is by far the most valuable one.
Find somebody you trust to hold you accountable for achieving the tasks you say you’re going to achieve.
Make a deal with them that there will be some kind of negative repercussion if you don’t meet the agreed deadline.
In an ideal world, you’d find somebody who has similar goals or ambitions as you, so that they’re actually able to comprehend the value of what you’re working toward, and you’re then able to motivate each other at the same time and push each other to work harder.
This is why the environment you are working or living in is so important.
Start Where You Are, Use What You Have
If you’re waiting to feel ready, you’ll be waiting forever.
It’s supposed to feel like you’re going against the grain. It’s supposed to feel hard. It should be an expectation that you’re going to feel completely lost and have no idea where you’re going to head next.
That’s the whole idea. You’re pioneering the way forward. If it was paved out in front of you, everyone would be able to walk down it.
The only way to overcome the imposter syndrome is to do enough hard work, and get enough reps in, that you feel as if you genuinely deserve it.
“You don’t become confident by shouting affirmations in the mirror, but by having a stack of undeniable proof that you are who you say you are. Outwork your self-doubt.” - Alex Hormozi.
It all comes down to this.
Get the reps in. Perpetually iterate. Realise that your first attempt will have weaknesses. Make sure that you are ruthless about identifying what went wrong, and be intentional about fixing it up and doing whatever you can to not make that mistake again next time.
If you can do this, it is impossible not to succeed.
All you need to do is conjure up enough willingness to keep getting back up and dusting yourself off after each iteration.
Learn from the Mistakes of Others
A smart man learns from his own mistakes.
A wise man learns from the mistakes of others before he even makes the mistakes himself.
“If I have seen further, it is by standing on the shoulders of giants” - Sir Isaac Newton
Everything we see around us is the result of generations and generations worth of hard work, iteration and building upon the foundations of each generation that went before them.
Keeping that in mind, how many thousands of people have fallen for rookie errors and wished that they could warn people that come after them so that they don’t fall for the same things?
Wouldn’t it be incredibly valuable if there was some kind of well formatted document that outlined exactly what these people fell for, and how they overcame it?
It’s worth the investment of taking time to research what pitfalls you may be able to avoid, before making them yourself.
- Read biographies of successful people throughout time.
- Study history, and how previous leaders and empires have risen and fallen.
- Search for practical resources or roadmaps within the specific industry or niche you want to pursue.
Valuable insights on where people tripped up in the past are sitting there for the taking.
Opportunity Is Abundant
Think about it like this.
How many people in today’s day and age are completely fine with settling for their average salary 9-5 job?
How many people out there even possess enough courage to leave that cushy environment, take the risk, and actually build something themselves?
There are more opportunities and people with problems that need solving than ever before in the history of mankind.
At the same time, less and less people are willing to step up to the mark and put themselves in a scenario where they even have a product or service to sell.
At first, it may seem as if you’re an imposter on the outside looking in. It may feel like you’re not ready. But if you switch your perspective, you’ll realise that the odds are skewed in your favour.
You don’t have to have it all figured out.
You don’t have to have been the smartest kid in your class who scored A+ right the way through school.
You don’t have to know exactly how to build everything, how you’re going to market everything.
All you have to do is start creating something, today.
Commit to consistency. Continuously show up. Be ready to fail, a lot. Anticipate failure. Perpetually adopt a student mentality. Rigorously identify and iterate on what doesn’t work. Keep your head down, and get the reps in.
If you genuinely follow this, you cannot fail.
- Cole.
If you’re interested in transitioning from a traditional 9-5, leveraging AI to build a future of your own, and capitalising on the digital renaissance, subscribe to my weekly newsletter.
You can also follow me on twitter @cole_mccon