Andrew McAvinchey
By Andrew McAvinchey on March 21, 2022

The (Irrational) Obstacles to Success that We Place on Ourselves - and How to Overcome Them.


We all want to be successful in life. But often we are our own worst enemies when it comes to achieving our goals. We put up obstacles to success that seem rational at the time, but are actually holding us back.

One of the most common obstacles to success is perfectionism. We think that if we can just get this one thing right, then everything else will fall into place.  But usually it doesn't work that way. In fact, perfectionism can often lead to procrastination and self-doubt.

Another common obstacle to success is fear of failure. We are scared to take risks, because we might not succeed. But if we never take any risks, we'll never achieve anything great.

A third reason often given for a lack of success is 'not working hard enough'. Hustle, pushing and working harder are considered by many to be the key to success.  But often, it's not just about working harder. It's about working smarter. And that means taking the time to rest and recharge, so that you can be at your best when it matters most.

The key is to acknowledge where you're putting on the brakes, and then take action to release the brakes.

If you're facing any of these obstacles to success, don't despair. They can all be overcome with the right mindset and some simple tools to deal with them.

The first step is to acknowledge where the problem lies.  If you can identify the obstacle, it's much easier to find a way around it.

Once you've done that, take some time to think about what success looks like for you. What are your goals? What would it feel like to achieve them? Visualising your success can help to motivate you and keep you focused on what's important.

One of the most difficult yet useful questions you can ask yourself is:

How do I get in my own way without realising it?

Like many who lived through the pandemic over the past couple of years, I am grateful for the hours spent wandering the 2km radius near our home, forced to appreciate the little details. I learned to participate in the endless curiosity of my daughter. I didn’t want to get anywhere, I just wanted everyone to be safe and healthy.

The time I spent working with clients became more resolute and focused. Since I would rather be spending time with my family than working, every hour spent at work must now count for something. Through a process of elimination I began to notice some of the obstacles in my own business that were causing friction.

The further I dug into it, the more I realised I’d need help.

One afternoon, I impulsively told a bunch of strangers in a community forum that I was struggling a bit. This was a big move for me. I don’t like to stand out, so it was vulnerable and uncomfortable to share the difficulties I was having at the time.

Then a little miracle happened. I won a trip to Mexico City to attend the Dynamite Circle’s annual gathering of entrepreneurs. One long weekend of brainstorming and networking with some of the most inspirational, successful and independent people I’d ever met. It was a life changing trip.

Fun is the New Business Model: How One Weekend in Mexico City Helped Me Realise What I Really Needed to Succeed.

I went over there thinking I’d take a bunch of notes, learn business models, sort out my pricing, but it turned out that wasn’t what I needed.

One of my sponsors for the trip was @Gerbz. He saw my post that day and invited me to Mexico. He runs Bitlift, a podcast and community for learning about crypto and DeFi. I got to hang out with him and all of his Colorado crew for most of the weekend. They were so much fun.

@Gerbz put me up in a fancy hotel room and gave me one piece of advice. “Just have fun. The people you meet here will be far more valuable to you than anything you can learn.”

The evening before a day of mastermind sessions, I ended up in the back of a taxi with Itamar Marani. I’d seen Itamar speak at an event the night before and I was intimidated by him. He had answered a question from an audience member by bypassing the question and telling the guy that his was a mindset problem, and that without addressing his mindset, he would make no progress. It stung because this was also true of me. I guess it’s true of a lot of entrepreneurs. That’s certainly been my experience in working with CEOs… It’s definitely true for me.

Itamar calmly pointed out to me that what was getting in the way of success wasn’t a rational thing. It was irrational. Emotional. And that unless I found ways of working with the irrational, I would not progress beyond patterns that had repeated themselves for years.

Obstacles in Business: How to Identify and Eliminate Them

There are many things that can get in the way of business success, but often it comes down to self-sabotage. We can be our own worst enemy, standing in the way of our own progress without even realising it.

One way to identify these obstacles is to ask yourself how you get in your own way.

Here is what I’ve learned:

1. Being open with other people can help you see your blind spots

The first day of mastermind sessions, I broke down in the first five minutes and just asked for help. I told them I had issues. 6 people I’d never met told me I wasn’t the only one and gave me a bunch of encouragement I wasn’t expecting. It was the beginning a journey, where I met people who were honest about their weaknesses and didn’t mind leaning on other people for help with things they couldn’t figure out on their own.

This was new for me.

2. Your history is not all that it seems.

I thought I was a bad employee. That’s essentially why I started my own business. I’d tried a few jobs in corporate roles before I decided that I was just not cut out for it. I needed to be my own boss because no boss would put up with me for long enough.

This isn’t true. I checked.

One of the first things I did when I came back from Mexico was to get in touch with my old boss. He’d sold his company for millions and I’d lost touch with him over the years. We’d always had a good relationship and he’d encouraged me a lot when I worked for him. He also fired me.

We met for dinner and our conversation went something like this:

“I’m a terrible employee”.

“No, you’re not. You’re a good employee. I fired you for reasons that were not personal”.


I was kind of shocked. I’d assumed I’d made a balls of that job. I ran off to India just as we’d started to expand the company. In reality, I was afraid of the new CMO he’d hired, who I perceived as a threat. I was afraid she would expose my weaknesses. I left before that could happen. It turns out it didn’t matter.


3. You shouldn’t try so hard to be good at the things you are terrible at doing

I was introduced to Bob Moesta by my brother. Bob is the co-inventor of the Jobs To be Done framework. Bob likes to help people to progress.

My business advises clients on business strategy and growth, so it would make sense to ask Bob about that right? After all, it worked for Intercom…

Except I met Bob the same week I’d met my old boss. I was fresh off the plane from Mexico where my irrational fears and emotional blocks had been exposed for all to see.

I was ready to have an entirely different conversation with Bob.

My conversation went something like this:

“Bob, my problems are irrational. What is preventing my progress has little to do with anything that I’m aware of… I’d like to figure out what could be holding me back. Can you help with that?”

“As a matter of fact, I have just invented a framework for that very thing! Would you like to be a guinea pig beta user and I can take you through it?”


As the inventor of a framework to improve how people use and ‘hire’ products in their lives, Bob has turned his attention to how people hire other people to do jobs, and how employees understand and position their value so that they can be hired.

38% of people are miserable in their jobs.

Bob asked me:

“Are you an entrepreneur because you had something you had to do, or because you felt you couldn’t get a job”

I told him about my experience with my old boss, how I’d always thought I was a terrible employee. How I was wrong about that.

Bob said “Let’s start there.”

We broke it all down over the following 3 months. Every week I got to sit down with Bob for an hour.

What I’ve learned is that many of us, including me, are under the impression that we have to be good at everything in order to succeed.

I’ve spent a lifetime and a lot of energy covering up the fact that I’m pretty bad at a certain skillset and no matter what I do, I show no signs of improving. Consistency, discipline and focus are hard for me. Yet these skills are essential for entrepreneurship. In more than one job, I tried to convince my employers that I was good at these things. It was a matter of time before my weakness was exposed, so I usually left before I was found out.

Meanwhile I’d under-valued other skills that are in short supply. Strategy, innovation, connecting the dots. I’m really good at connecting the dots.

Bob explained to me very simply that I’d never be excellent at the skills in which I’m not naturally gifted. And I don’t have to be. More importantly, by spending my energy trying to cover my weaknesses, I’m preventing my own progress.

I’ll never be a project manager. Or an accountant.

I’ve learned to hire for my weaknesses, instead of wasting energy over compensating. This frees me to work on my strengths.

4. Know what you want.

Decisions are usually not binary. Most decisions don’t have a simple yes or no answer.

Making a decision is binary though. Once you’ve made a decision, you’ve progressed in a particular direction. You go left, or you go right. You can’t go in both directions at once.

I needed help understanding the dimensions of making a decision, and tools to use when assessing those decisions before I took the leap.

Previously when faced with a difficult decision, I’d do this mental arithmetic where I’d calculate the risks, then I would imagine everything that could go wrong. I’d guage how excited I felt and ultimately make my decision based on a gut instinct. I’d balance the gut instinct with any red flags I could perceive, and ultimately whichever tipped the balance won the decision.

This isn’t a terrible way to make decisions. It served me well over the last 40 odd years. Using this method, if you’re clear of incorrect assumptions and you have all the facts, you can even make the right decision from time to time! It’s a bit random though, and crucially this method doesn’t allow me to make choices rationally when emotion takes over. In stressful situations, I’ve made decisions that didn’t work out well purely because of the mood I was in that day.

By designing and using mental models to assess situations according to a matrix of requirements, my decisions became easier and are now less driven by emotion.

For example, working with Bob Moesta, I created a grid of 9 variable needs I have in any career, job or project. Here is a sample of the decision matrix that I developed with Bob. This is a simple spreadsheet that reminds me what is important to me, so I don't forget, and so that I can weigh my decisions rationally.

These include having autonomy, having the ability to solve complex problems, and stability. Your criteria might be different. Yours might include flexibility, systems that tell you exactly what you need to do each day to be valuable, and a boss who gives excellent feedback. It varies for each person, but it’s important to know what’s important to you.

Now when looking at any decision that involves a job or project, I can pass the decision through the filter of these 9 variable factors. I weigh each according to their importance and end up with a score on each of the decision points I’m facing.

It is a very rational way to look at decisions that can sometimes be very emotional.

As Bob’s guinea pig, he tasked me with assessing and evaluating a whole range of jobs and careers other than my own (entrepreneur/consultant) to truly understand my choices.

I looked at my entire history, evaluated past jobs, assessed the job market and interviewed loads of people who had jobs that looked interesting.

By doing this I was able to get a realistic sense of what each job could provide, where the trade-offs would be if I did that job, and how each ranked against my choice to be an entrepreneur.

This way of assessing decisions about my business, my career and my life has changed everything. I can now understand the trade-offs I need to make to progress, where I need to focus my energy, and ultimately how to be more successful. I have a set of tools I can use in any situation to assess a complex problem, apply a system of discovery to understand it better, and ultimately to progress in a way that serves me and my family in the best possible way.

As Bob said, “You’ll never again feel insecure about work, since now you understand completely how you can help others and what you need to help them”.

5. Know your own false beliefs and work with them.

Remember my taxi ride with Itamar Marani?

A few months later I signed up for his Arena Mindset Accelerator program.

Through a revolutionary program over 6 weeks, Itamar provided me with the tools I need to deal with myself. I was able to add another piece to the puzzle of irrationality.

It wasn’t easy to go through the program, but nothing worthwhile ever is. I feel like I’ve developed a superpower.

Working in an entrepreneurial context, I’m often in situations that cause me to feel fear, stress or anxiety. Coupled with world events, family life and an uncertain future, my tendency to be driven by impulse or reactions without fully considering the consequences has increased.

What I’ve learned is that it isn’t necessary to become a Zen Master to be successful. Uncertainty and fear are natural feelings, as are optimism and excitement.

Where I’ve taken a mis-step in the past has predominantly been a result of a calculation I made without being fully aware of all the influences on my decisions.

Some of those influences are often subconscious beliefs that dominate my decision making without me even realising.

In my case, I have laboured under a very convincing illusion that in order to be successful, it is inevitable that I have to fit the mould of what my culture and society deem fit for success. It might be an Irish thing, but the class system I grew up in (a leftover from British colonial days perhaps?) and the inherent Catholic guilt I associate with business, money and enterprise has eaten away at me from inside during every important decision I’ve made in my life.

It’s hard to look back and see all the times when this subconscious belief somehow over-rode my logical choices in situations where an opportunity presented itself, or I put myself into a situation that was not good for me.

I now have a system of tools I can use to recognise the cues, the little giveaways, that are present when I am being influenced by the irrational part of my brain. It doesn’t mean I’m any better at dealing with it, I can just recognise it is happening in time so that I can make sure my decisions are made rationally, without unnecessary influences corrupting the opportunity and my ability to progress.

Here’s a recent example:

In some way I believed that if I changed my business by bringing in a partner, I’d have to change myself to be someone I didn’t like. I’d be over-worked, and ultimately I’d be ruined and/or die.

I told you it was irrational! These thoughts were unconscious, yet these and many like them have dictated my strategy for over 5 years at least.

I now realise I’ll never be good at an essential component of any business. Consistency, processes and repetitive tasks. Nope, sorry, can’t do it.

I need someone to lead on the ‘operations’ side of the business if I am to be successful.

Now I have a way to recognise when thoughts like these are sneakily hiding behind what looks like perfectly rational decisions that I make every day.

In the example above, the giveaway cues were that I was avoiding work for at least two days. I was having a great time - long walks, taking the whole family for coffee and croissants, reading a book…

I caught myself procrastinating and simply asked “Is it possible that my behaviour at the moment is a result of a belief that I need to mould myself to fit the culture right now. That I’m reacting to an idea that I have to become someone I don’t like in order to be successful?”

Turns out that well... that was indeed what was going on yeah... I'm not proud of it, but that's what was happening. And it would have continued to get in the way of progress if I didn't acknowledge what was driving my decisions - irrational fear and false beliefs.

Facing Your Fears and False Beliefs to Achieve Success

In order to be successful, it is essential to face your fears and false beliefs. These may be subconscious beliefs that you are not even aware of, but they can influence your decisions in a negative way.

We've discussed the importance of recognising when irrational thoughts are influencing decisions, and how this can be done using a system of tools. I gave examples of how I recently recognised that I had been influenced by a subconscious belief that if I changed my business, I would have to change myself as well. This prevented me from making important decisions that would help me become more successful.

It’s not easy sharing all of this. I’m normally a very private person. I’ve developed many shields over the years to protect myself. I’ve found ways to cover up my vulnerabilities and weaknesses so that I could appear strong and confident.

Putting it out there makes me feel uncomfortable. Letting people know that behind the scenes that there’s a bunch of stuff going on that not even I understand is scary.

Dealing with it myself can be a challenge.

That's why I asked for help. I'm glad I did.

I’ve been blessed this year by being visited by many guiding angels on my shoulder.

Each has helped me to see the world more clearly.

I understand myself better.

One thing I realised is that I’m afraid to stand out.

To be seen.

I have a lot of false beliefs to back up that fear.

To honour those who have helped me this year, and to give myself a chance to shine, I decided to launch this blog.

If anything, it’ll give me an opportunity to learn.

I hope you enjoy it.

Please let me know if you do, and connect with me here or wherever you hang out online.

Published by Andrew McAvinchey March 21, 2022
Andrew McAvinchey