Make the Right Mistakes

by Timothy on May 1, 2011

Should you Make Mistakes?

All courses of action are risky, so prudence is not in avoiding danger (it’s impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.
– Niccolò Machiavelli

Mistakes of Ambition vs. Mistakes of Sloth

For a long-ass time I felt guilty about my mistakes, missteps, moments of losing money, etc…

But as soon as I learned about the difference between the two kinds of mistakes (thank-you Tim Ferriss) I immediately realized that I’ve simply been making mistakes of ambition – from really “going for it” in life… not from sitting around praying good fortune will strike, then feeling upset when opportunities have passed me by.

And the experience and learning that has come from said “Mistakes of Ambition” are simply the grooming period – the seasoning – of ME… the lessons of life that I’m acquiring first-hand and “in the real world”. And that is *priceless*…. literally – money can’t buy you that kind of perspective and experience.

The $100,000 question

Ask yourself – would you rather invest $100,000 with someone that has been DOING it for years, and has both the victories and failures, the insights and the stories, and the developed “sixth sense” for things…. or would you give your hard-earned dollars to a newbie?

Or worse-yet – would you give your $100K to a slick salesman who isn’t really a business person, but rather a polished advertisement for their company with just enough “credibility indicators” to come off as believable?

(Credibility indicators include: academic training, letters after one’s name, membership in industry associations, press, etc…. even though I personally have all of these myself, trust me – it isn’t those things that have brought me to where I am today.)

Not All Mistakes Are Created Equal

In the daily pursuit of building my legacy, I’ve made a TON of mistakes: I’ve lost money, I’ve lost customers, I’ve lost deals, I’ve said the wrong thing to the wrong person at the wrong time, I’ve been rejected, I’ve lost competitions, I’ve been embarrassed, I’ve felt publicly humiliated.

Does that put me in the same category as someone who sits at home night after night silently suffering an unconscious, uninspiring existence as they drown their slow suffering in reality TV?

Am I in the same class as someone who has missed tons of opportunities because they’ve been sitting on the sidelines of life?


Mistakes of Ambition are not the same as Mistakes of Sloth.

The Strength to Suffer

I can’t tell you how sad it is to see people suffering day after day with no end in sight. Despite what your peers tell you (and you tell yourself), this is *not* some kind of honourable “cost of doing business”.

Now I’m not talking about the discomfort of taking action on new things that are outside our comfort zone. Nor am I talking about the “pain” that an athlete “suffers” from pushing out one more rep.

Nor am I talking about the reality that “sometimes success is 1% inspiration and 99% perspiration.”

I’m talking about the business owner that silently slaves away with no end in sight, no idea how to change things, and isn’t willing to ask for help.

Tim Ferriss refers to one of his businesses (in it’s earlier days) as a train headed downhill on a crash course with him shovelling more coal into the engine for lack of a better option.

Well said.

Beyond Business

I’m also talking about the person in a loveless marriage that doesn’t have the courage to have the uncomfortable conversations they’re deeply, secretly desperate to have.

I’m talking about the employee who finds no joy from their job… living a comfortable, although wholly BORING existence… in a life that is just comfortable enough to keep going, but not anywhere near exciting, interesting, or memorable. This person will die and few will notice.

…is this the existence that we are supposed to develop the “strength to suffer”?

HARDLY. Sounds to me like the “walking dead”.

The BIG Picture

This isn’t about employee vs. entrepreneur, “E-Quadrant” vs. “B-Quadrant”, or anything like that.

This is about: do you feel that you have an exciting future ahead of you? Does tomorrow look more promising than yesterday? Or at least next month vs. last month?

Will the parts of life that are already great be as good or better? And the parts that are brutal either massively improved, or perhaps totally eliminated?

No Honour

There’s no honor in silently suffering, and “staying the course” because of (insert excuse here).

Wake up, take the reins, and make life happen FOR you, instead of TO you.

Why I Avoid Optimism

Let’s face it: some days suck, and some things we have to do are totally un-enjoyable. I stick to what author Jim Collins describes in his fantastic book Good to Great…. “The Stockdale Paradox”…

Admiral Jim Stockdale was a Prisoner of War in Vietnam, subject to torture and bad living conditions for many years. What he learned – and what he taught his fellow soldiers was this: Face the cold hard facts (e.g. I will be tortured today), and have an unwavering faith that one day you shall prevail.

While this is certainly a dramatic example compared to the day-to-day challenges we face as entrepreneurs, the heart of the message is perfectly accurate.

When someone loses the second half of this passage – to have unwavering faith that one day you shall prevail – and does nothing about it, this is the formula for the “walking dead”.

Wishing You All the Best

I encourage you to courageously move forward in the path of your dreams….

Take action, take calculated risks, make mistakes, win, lose, lose again, lose again, learn a ton, win again, learn some more, grow, work on yourself, and…


Onwards and Upwards,


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