7 Truths that Explain Why You’re Winning Less than You Could Be

In a world in which most people are busy covering truths to save face and be nice to one another, sometimes we just need some words of honesty to help those who really need it.

If you’re not seeing the results you want yet, it could be that you and those around you are not being totally honest with you. It’s understandable. The truth can be painful. But the truth is vital, because it’s only through truth that we can do what needs to be done without being misguided through sugar-coating.

The following are a handful of reasons that could explain why you aren’t where you want to be yet.

  1. Your focus is too shallow
  2. You’re too nice
  3. You’re too comfortable
  4. You’re a wuss
  5. Your product or service sucks
  6. You underestimate the tiny steps
  7. You don’t believe in yourself

My awareness of – and commitment to – each of them has allowed me to guide myself to a simply better, more focused life.

These are primarily written as reminders for myself, based on my own lessons learned, because I’m not perfect, and if this reaches a few more of you, all the better.

1. Your focus is too shallow

Our ability to do, as Cal Newport calls it: ‘deep work’ – work that is free of distraction, rich in flow, and deep thought over longer periods – is becoming easier to neglect.

We all know the reasons why it’s becoming more of a challenge to focus on fewer things more intensely rather than spreading our energy thinly and chaotically across multiple areas.

But for those of us who understand the importance of dedicating energy to very specific skill-sets, and developing mastery in fewer areas, the modern world does not have to be an excuse for our avoidance of it.

Clarity about what matters provides clarity about what does not. –Cal Newport, ‘Deep Work

We just need to prioritise the important stuff – the things that needs lots of time and focus, day in day out, and block out the rest.

Because most people are zombies in a distracted environment, those of us who invest time in one or few things that matter and have the potential for growth and refinement have an enormous advantage.

There’s no hocus pocus in what I’m telling you. It’s all cause and effect.

Spend more time honing something specific with more focus and less distraction.

You will win if you can do more of this. Don’t listen to what others tell you about diversification. Are they successful?

Anyone who achieved anything meaningful put a lot of focus and dedication to one thing, at least to start. They may have unravelled, but at some point, they focused deeply for a significant stretch of time.

What could you do today that puts more attention towards those master skills that will provide benefits long into your future?

2. You’re too nice

Being nice has its boundaries. Being positive and friendly, good. Being nice to everyone to try to be liked, not so good.

Unconditional niceness, good. Conditional niceness, lame.

Nice to lift someone up, great. Nice to get something in return, weak.

Being overly nice could be damaging your ability to truly connect with people with honesty and be taken seriously.

As an independent professional, your most important asset is the respect that others have for you. If you continually sacrifice your own needs for others, you’re disrespecting yourself, denying your worth, and allowing others to do the same.

This approach applies to self-promotion and even belief in our own ability to create new work. Many of us fail to sell ourselves because we don’t want to offend or encroach on others, at the expense of our own recognition.

We don’t feel comfortable rocking the boat, infringing on someone’s time or asking for help. But these are all things that are required of you to make progress, get seen and be taken seriously as a professional.

All of these require the strength to be vulnerable in someone else’s eyes, which is not comfortable. Yes, self-promotion makes us all vulnerable, and uncomfortable.

Quit being so nice at the expense of your own growth and your needs. Be real, be positive, be bold, and speak truth.

Put your attention to enhancing your own value rather than trying to impress others and covering over your flaws. Striving to impress is a sure sign you lack faith in your own value. With real value, you don’t need to impress anyone.

“Try not to become a man of success, but rather try to become a man of value.” Albert Einstein

I want you to do this one thing for me today:

Contact one person you’d love to work with or have as a mentor and tell them: 1) exactly what you need (a new job, money, experience); 2) exactly what you can provide them, and 3) exactly how you can help them without sugar-coating it. Don’t be nice, be real.

Do this now and email me with the result.

Don’t email me until you have received a response. This may take several contacts to this one person.

3. You’re too comfortable

A lot of people say that life is hard, and that’s why they’re not progressing in life.  For some, particularly in tough, war-torn parts of the world, this could well be the case, but for most healthy people, this is nonsense.

Life is not hard if you focus on what is possible with what you have.

Most of us have everything we need. Most of us have the luxury of access to the Internet and the freedom to watch sitcoms and movies. Most of us are not at war. Most of us have a roof over our heads and a comfortable bed to sleep in every night.

Access to jobs, happiness, luxury, freedom and money is all there.

Your comfort is actually diluting any sense of urgency to succeed in your life, because you already have comfort.

Humans are interesting. We are built to do our best when circumstances are tough and our backs are against the wall. We are all here primarily for survival. When our survival is not at stake we relax and fatten.

Our comfortable lives make it easier to stay where we are and stay average. To progress and make a difference requires urgency and something bigger to aim for.

You then need to reframe your situation, limit the comforts you give yourself and focus on the reasons for doing what you do, which truly fire you up.

What fires you up? What gets you angry? Who are your enemies and what are you doing to put an end to their advances? 

Sometimes you need to remind yourself of this every hour of the day.

These reasons need to go beyond having more time to put your feet up and watch Netflix with a slice of pizza. Why? Because this would mean changing your life by a factor of zero.

There’s an interesting aspect of the stoicism philosophy that I’m trying right now, which is to remind yourself extremely vividly of what life would look if you were really struggling, or at least uncomfortable.

This evocation of the negative sounds like a wrong move, but what you’re doing is awakening yourself to what you don’t want, so that you’re enlivened to do what you do want.

This fires our survival mechanisms again, and creates action.

Remind yourself occasionally of when times were really rough for you. Do you want to experience that again? Feel it viscerally and this will motivate you to change.

I’m more conscious these days about falling into comfort, because I know that comfort leads to being caught off-guard. If I’m getting in plenty of paid work and things are going well, this is a time to push even harder.

I treat my comfort like a thermostat. I know that if I get too comfortable and don’t push my boundaries and take risks, I’m sliding backwards and I need to adjust.

Years can go by like this, feeling like you’re progressing because you’re getting jobs done and replying to emails and fighting fires and winning browny points with your husband or wife, but you’re sliding backwards because you’re comfortable.

Continually test yourself. Take away a comfort once in a while. Forget trying to make every day run by without a hitch or without awkwardness. Stop striving for comfort. Move away from it. Create contrasts.

Infuse some danger into your life, and watch your life change.

4. You’re a wuss

I’m not insinuating that you are innately weak. I don’t know that you – yes you – are actually reading this.

We all have strengths and we all have power and courage beyond what we can imagine for ourselves.

You just might not be pushing hard enough, and this ties in closely with being too comfortable.

Sadly, a comfortable world has led to the majority of us being moulded into weak, scared, jumpy and stressed global citizens.

But you have the choice to change that.

Whether you like it or not, taking courage is the one single thing that will make the most difference in how lucidly you experience the truly fulfilling things in life.

For the most part, we all know what we need to do in order to see positive change in our lives and careers. But we’re scared, and we often act – not on our goals or our purpose – but on our fears.

Fear is the great block that stops you from getting what you want, though you don’t need to listen to it.

You can choose to be strong and do things that feel awkward and uncomfortable, because you know you must.

If there ever was a life hack that got you results most effectively and most rapidly out of any other, it is in doing things that take courage.

“They say: Think twice before you jump. I say: Jump first and then think as much as you want!” Osho

When I started coaching people over the phone months ago, I was terrified. I didn’t think I knew enough to charge money to help someone, and I was socially anxious on the phone, let alone on a video Skype call. But I knew I had to do it, and I just did that first call with a pounding chest.

Just because you have fear doesn’t make you a pussy. Allowing it to guide your decisions when you have the choice to overcome a necessary challenge, does.

Hundreds of calls later, my discomfort has for the most part melted away, and I’m able to let that confidence seep into other areas of what I do.

Taking that first step and staying with it was one of the best things I could have done.

These courageous actions don’t have to be gigantic. All it takes is tiny actions.

What fears are holding you back, and what small thing could you do today to show the fear that you’re not going to cower in submission any longer?

5. Your product or service sucks

Some of us just aren’t there yet in a particular skill or craft. What I mean by this is that your work is not of a quality that can consistently stand out and benefit the user.

You can’t let your ego protect the fact that you still have work to do to build something truly valuable and meaningful.

Of course you never will reach perfection, but not everyone stands on the same rung of the ladder either.

Life is truly a journey that provides us with feedback at every step of the way. Use the feedback to shift tracks if you’re in the wrong thing, or use it to hone that skill further.

Be careful about shifting and changing too much, however. Here’s a secret that I’ve uncovered that is irrefutable for me: there is no path laid out for you.

You carve your own path, and this requires making a decision first and working at it second, followed by more decisions.

Few skills worth working on are developed in a hundred hours. You need to commit to spending thousands of hours on something specific and not get deviated.

Passion comes later, not in a flash of inspiration. Passion grows out of the sense that you are improving in something.

Just make sure that when you choose something, it has potential for you based on your strengths and talents.

Digital illustration might never have become something I developed a level of mastery in if I hadn’t initially found it interesting. Thousands of hours of honing my style and approach has kept the passion alive and growing in that area for me.

Have faith. It might just be that you’re still in phase one out of ten.

You’re not immune to going through the process, like everyone else. You have space to grow, and you will become a master if you find something you’re willing to spend a lot of time on.

6. You underestimate the tiny steps

Since this post features a lot of secrets, I will let you in on another one based on my experience and deep thinking on the subject.

This won’t be news for many of you, but I need to remind myself of this every single day.

Anything worth aiming for is composed of thousands, even tens of thousands of tiny positive steps. Good health, a career of real value, profound expertise, a solid social network, happiness, and millions in the bank requires tiny, often seemingly meaningless actions.

Here’s the thing. We’re all programmed through society, conversation, movies, and stories of lottery winners and sports heroes that success is an event.

In reality success is a stream of small positive actions (tiny events) that are held together through your wit, awareness and determination.

When I talk about using a limited list of contacts (the Value Network) with my students in order to land opportunities and clients, the strategy requires stringing together many hundreds of tiny actions for results to form.

Sending three people an email each day feels meaningless, boring and mundane to most.

Even though small actions like these are tiny in and of themselves, they in actual fact hold massive significance. When strung together over time, small actions make the difference between something happening, and nothing happening at all.

Don’t underestimate the tiny, positive steps. They are hard to do because we want results now. Small steps feel like nothing’s happening.

Understand that small steps are actually massively significant, and success is a stream.

You can achieve anything with this philosophy put into action.

7. You don’t believe in yourself

Your reality is determined by your psychology. How you think determines your attitude and your actions.

Do you think those that truly believe they are a good person; those that genuinely believe their product or service is a great one; those that know they can handle situations, no matter what, experience a different reality than those who do not?

Of course they do.

No one is born confident. It’s a practice and a muscle and it takes replenishing all the time.

The best thing you must do if you lack belief in anything, is to experience real repeated success. This is why you will be depressed following repeated failure.

This repeated success need only be comparatively tiny and most of it is entirely in your control. If whatever it is is a slight improvement on the previous, that’s success.

Now you need to take the tiny steps approach from above and apply that to creating wins in your life. Over and over again. This is what belief is built on – an accrual of little successes.

With belief comes the positive feedback loop that enables your success and your ‘luck’ to build and your creativity to flourish.

You just need to be conscious of what you’re doing that sabotages your little wins, and what you’re doing to actively bring more of them into your day.

There is something else we all need to do more often to increase belief in ourselves and our work…

…That is to make our own value vividly clear to ourselves.

This means immersing ourselves in what is good about our work and our lives. It means listing out everything that is a strength in what we create and how it is helping people or potentially so.

If you are unclear about how much real value you possess, you will struggle to be motivated to express yourself and promote yourself.

If you found a book in a deep forest that contained the cure to all of the world’s diseases, what would you do with it? You’d do your damnedest to get it in the hands of the right people.

This is how you need to think of your work – as it is today, and what it will become.

You need pride in your work, but you need an unwavering belief in how you and what you do is truly useful, whether it’s in a tiny detail or in its entirety.

Are you betting on what is happening to you or what is happening because of you?



  1. I understand that you’re attempting to be “honest” but find a word other than “pussy”. It distracts from any value presented by this article by causing your reader to doubt your social intelligence. Thank you.

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