Finding Success Through Failure

Posted On July 24, 2021

4 min read

The greatest lessons you can learn regarding success are often rooted in a story that starts with failure. My own success of the past 10 years is rooted in a very specific failure, losing my job. In a scenario that came down to “fire me or I quit”, I was able to completely change my life, in a way I never would have otherwise, and hadn’t the 10 years prior. It wasn’t easy, and it didn’t initially feel great.

Losing your main source of income is terrifying.

But I have been in a situation where I have quit a job or been fired before, and since I learned from that experience I had spent over a year preparing for this. I had written my resignation letter months before and had been taking steps for exactly this moment knowing that one way or another it was going to happen.

Which means my income wasn’t immediately $0.


But in a decade I went from earning about $30,000 a year, to earning $300,000 in the year of 2020. That is not said to brag, it is something that I didn’t fully understand until reflecting on it more, and realizing the lesson.

From age 17 to 27 working from someone else could only take me so far. If I had continued down that path I could only expect similar results to what I and others had experienced. The majority of people don’t reach a high income by working for someone else.

The majority of people with financial freedom and time freedom, tend to be self-employed. While this may feel unattainable, it doesn’t have to be. Most people are just thinking about how they can skip to a better life than they have now in the shortest amount of time possible.

Achieving my outcome was a decade in the making, with possibly a decade of prep work beforehand and I’m very upfront about that. Going from age 17 making $6/hour at the mall to making 6 figures even in Passive Income is something that was a 20-year long journey.

However, with the knowledge, I am trying to pass on I am seeing people get there even at a young age in 5-10 years even if their path is slightly different but uses the same principles as mine.

Nothing I ever did had a perfect outcome or great result the first time I did or even the first dozen times.

This has been true of my artistic abilities in drawing, writing, and photography my whole life. Failing to get it perfect, get it right, or even something I didn’t want to ball up and throw in the trash, meant I kept refining it. And while it never became perfect it became good enough to get me somewhere.


Continuing to pursue improvement is meaningful. Failure provides you with an insight into what needs to be improved to produce a satisfying result. The main thing is to not be discouraged and to continue to learn from your mistakes as you make them, and apply those lessons until improvement reveals itself.

Failure forces us to change our approach. Insanity is doing the same thing over and over expecting a different result.

When I left my job what changed was that I became a full-time freelancer.

This meant I had to spend time prospecting for clients and opportunities, but it also meant I wasn’t limited by an hourly wage, a fixed salary, or any income cap. I could set the rates for the value of my work and would have to find people who would and could pay it.

This was by no means easy, but that wasn’t the point. It wasn’t about it being easier, it was about having more control. It was tremendously difficult at first, but eventually, I was able to also come to the realization that I didn’t need to spend more time working than I had at my job. I had more time to find other ways to produce income. So I expanded into other areas and new opportunities like YouTube and Affiliate Marketing and eventually public speaking and workshops.

So now I had multiple streams of income from various different activities, where before I had one income from various activities my employer would have me do for a single paycheck.

I was utilizing the same skills but I was deploying them differently. And in some ways I wasn’t working “harder” but I was putting that effort to a different purpose, and also reaping the majority of the benefit.


Do you have a specific idea of what you would want to have in terms of a career and lifestyle? It’s important not to be vague, you can’t work in a specific way towards a vague outcome. You need to know what you want.

If you know what you want, specifically start looking for examples of people like you who have achieved those outcomes and try to learn what their processes and skills are.

The fastest track to cashflow is usually offering your services:

  1. Learn or improve skills that have a clear market value
  2. Spend 1-2 hours a day prospecting and trying to find clients or leads
  3. Build your presence on LinkedIn and also join Facebook Groups
  4. Create a strong body of work to showcase your skills and value
  5. Actively network with the intention of finding specific opportunities





Written by Roberto Blake

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