The lessons we learn through failure are those that shape us in success. My remote life transition wasn’t easy, especially from a working and career perspective – it’s taken some time. Looking back has been a very valuable way for me to realise that even whilst failing, I was, and am, learning new skills for future success.

I’ve missed more than 9000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game-winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.

Michael Jordan

I’ve always liked this Michael Jordan quote, as a basketball obsesses teenager of the nineties, he was the king of the hill, numero uno. Some of MJ’s fails might have been behind the closed doors of the practice court but some were glaring. In this article, I look at why failure has been good to me during my remote life transition.

I embarked on the remote life due to the lure of travel and exotic destinations. But, to me, the most impressing advantage to the remote lifestyle did not lay in those beautiful destinations. Many people work for forty years whilst tying their hopes and dreams to those twilight years of their life when they have time and financial freedom. I wanted that freedom right then, no delays, no procrastinating, no wondering why I couldn’t do what I wanted to. And perhaps that’s why the common person dreams of becoming a millionaire – it buys them the freedom of time and choice.

About 18 months into my travels, something special happened. That first year and a half had been an incredible time for me as I relished the opportunity to see the world on my terms. However, I had been living on relative fumes, churning through the last of my savings and just about keeping my head above water.

remote life transitionInitially, I had tried to launch a business that helped marketing agencies with online competition services. I thought it worked well because I could do it remotely and I had a wealth of contacts in the sector. I quoted some nice jobs and had some offshore developers build mobile apps for me. Six months in and my experience with offshore developers was dramatic, to say the least. None of my quotes were ever successful.

My only “work-related” enjoyment came from the launch and regular articles I added to my travel blog. I never intended for the blog to be an income earner – you’re not going to do that with single digit visits each day and an audience made up of your mum.

Time for a startup worthy “pivot”, that transitional word that means you’ve failed but you’re trying to salvage something from the wreckage. With my love of writing combined with my love of basketball, I decided to give freelance sports writing a shot. And I loved it! When the NBA highlights were rolling my girlfriend could no longer claim I was slacking – this was research! The love affair of being a writer continued for a couple of months and I wrote some good content but I was faced with the looming reality that it would take years for me to generate a basic income from this type of work.

I have no definite talent or trade, and how I stay alive is largely a matter of magic.

Charles Bukowski

remote life transition
Perhaps the photo that best matches the Charles Bukowski quote above, taken on a motorbike trip through rural Vietnam

Over next 10 months, I worked with some software developers in sales, rekindling a love/hate affair from some 9 years prior. But I did come to a realisation, with age I had become more level-headed within my approach, gone were the high highs and the low lows, I looked at sales as a combination of two things:

  • Play the numbers game
  • Continually refine your approach

Sometimes fate may also lend a hand. Through my rekindled experience of sales, I decided to write about the combination of traditional sales and modern sales – an article you can read here. The article was exceptionally well received on LinkedIn and an opportunity was born. I’m sure many sales people would love to work remotely. I’m sure they’d also like to know about the challenges and rewards of this lifestyle plus how you can be successful selling whilst working remotely.

remote life transition
My first article as the Modern Remote Salesman

Sometimes it is only when we stop and look back we realise the journey we were unknowingly experiencing. My previous fails had taught me the skills I needed to be successful in the modern era of sales. My work is now a combination of sales, marketing, growth hacking, PR, and content curation – largely skills I learned whilst travelling and living remotely.

I can identify leads, manage email marketing campaigns, curate SEO optimised content, tackle complex proposals, refine pricing models and budgeting scenarios in addition to a host of other skills and automations that have made me successful in remote sales.

Success consists of going from failure to failure without loss of enthusiasm.

Winston Churchill

It was all the failures that led me here. My remote life transition allowed me the time and freedom to make mistakes I could never have made in the corporate world. It’s only now that I’ve had time to realise this and I’m very thankful.


Steve is currently working with Australian SaaS company Qwilr. He is passionate about the craft of sales. Steve also provides ad hoc sales coaching and support to salespeople and sales teams looking to modernise their techniques and improve their results.

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