side-hustle success story

Side-hustle success story (and lessons learned): from full-time job to traveling indie-entrepreneur earning 2X as much in 1/2 the time [TPP#63]

IMAGE: Hayley and I at Angkor Wat in Cambodia on our 6-month travel adventure after taking my side-hustle full-time.

UPDATE: You can now learn more about my new “How to become a ‘virtual consultant'” program here.

This is a blog post I’ve been dreaming of writing for quite a while (and in fact, is a little overdue).

When I first started my side-hustle back in October 2014 I was working full-time in a marketing position. I had a good job, but I always wanted to work for myself; be my own boss, set my own hours (working a lot less than 40 hours per week) and work on projects that I care about. I’d get up at 5 am each day and hustle as much as possible before work. During the day, I would watch the clock and be itching to get back home and continue working on my business. I would dream of writing a post like this where I could share my story and transition from full-time job to independent entrepreneur.

I also know how hard it can be to leave your job and make the leap to full-time self-employment. Giving up a full-time salary to work for yourself is scary. Before you make the leap, you need to be generating a sustainable income that you can replicate each month. But how? And I know how many people out there are still struggling through what I had to go through. If this is you, I hope you can read this post and gain some insights on how to make your own transition to indie-entrepreneur.



So, what does my journey from full-time worker to self-employed indie-entrepreneur look like? Well, here’s the semi-condensed version:

2012 – Where it all began

  • April 2012 – In my final year of University I read The 4-Hour Workweek (and write a book summary) for the first time (I’ll end up reading it about 4 or 5 more times between then and going travelling in 2017).
  • September 2012 – I purchase the domain name,, and create a free WordPress website. I start blogging about nothing in particular, random ideas mostly. Have a look at the early posts. They're crap!
  • November 2012 – I finish my final University exams securing my Bachelor of Commerce Degree majoring in Marketing and Entrepreneurship. I begin a Marketing job at (an e-commerce store in New Zealand) where I learn about online advertising, social media, email marketing and what it’s like to work a 9-5 job.


2013 – My first job

  • Early 2013 – I’m loving my new job and soak up all the new lessons like a sponge. During my first year I work hard, learn a lot about how to be more productive and get rewarded with new projects. Management seems to think I’m doing a good job. I discover this new project management tool called “Asana” and share it with the team. Over the coming months, I help to transition the company to Asana and train over 50+ staff on how to use it.
  • May 2013 – Hayley and I purchase our first house and move in a month later. We spend most of the rest of the year covered in paint as we renovate and make the house our own.

house renovations

  • November 2013 – I complete my first half marathon and finish in 1:29:55 (I’m the last runner to come in under an hour and a half).

2014 – The side-hustle begins

  • Early 2014 – I’m enjoying work but remind myself that the goal is to be my own boss. After re-reading The 4-Hour Workweek I come up with the idea to create “Adwords for Students”; an online course to teach students about Google Adwords which they can put to good use in their first job (like me). I create a Kickstart campaign to fund and validate this idea, but it’s a total flop. In March I do Tough Mudder and injure my knee which continues to be a pain for the rest of the year and ruins my plans of doing the full marathon.

house renovations

  • Late 2014 – I complete Simon Sinek’s Learn Your Why course to learn more about myself. I use the insights from this to start blogging about productivity and self-improvement. I rebrand my website and set up proper hosting with Bluehost (affiliate link). My friend Chuck agree’s to be a guinea pig so I can teach him about productivity and come up with the structure of a coaching program.

2015 – My first online sale and product launch

  • January 2015 – Using the advice from What the Most Successful People Do Before Work (book summary) and The Miracle Morning (book summary), I start waking up at 5 am so I can work on my side-business before work. I also set up a MailChimp (affiliate link) account and create my first email course, The 7-Day Productivity Plan to get email subscribers.
  • February 2015 – I start work on a paid online course, The 6-Week Productivity Program which I’ll sell as an extension of my email course. I host a webinar to promote the course, 6 people turn up and the launch is a total flop. Back to the drawing board (again).
  • 28th March 2015 – I married my high school sweetheart, Hayley. Family fly all the way from the UK to New Zealand for the big day. We have a massive party and it’s the best day of my life.


  • 25th April 2015 – On a Saturday morning, I make my first online sale worth $9.99 selling an ebook version of my 7-Day Productivity Plan. I can’t believe it and run into the bedroom to tell Hayley. I find it weird to think that someone, somewhere in the world has sent me money to purchase a digital product that I created using a computer. This is a huge milestone!
  • Q2 2015 – I focus my energy on building my audience so that the next thing I launch will get a bit more attention. I put time and energy into writing for the blog, guest posting and I create The Productivity Podcast. Meanwhile, work is becoming more and more tedious. I’m getting bored, my progress has stalled and the excitement of working for myself destroys my motivation at work.

productivity podcast

  • Q3 2015 – I work on a new product, The Personal Productivity Toolkit which contains an ebook, videos, interviews and other resources. There’s a lot to do. I’m also trying to keep up with publishing regular content on the blog and quickly find there aren’t enough hours in the day.
  • August 2015 – I hand in my notice to leave my job. While I can’t support myself just yet, I pursue an opportunity to work with my buddy Chuck on his new mortgage broking business.
  • September 2015 – Hayley and I go on our honeymoon to Bali. We love it and as soon as we’re home, want to go back! I also begin my new job working in Marketing for, start learning about giving mortgage advise and train up as an adviser.

irefi team

  • October 2015 – I launch my Personal Productivity Toolkit and make my first few thousand dollars online. It’s not a runaway success, but it’s not a failure (for once). For the rest of the year, I work on improving the product and sales funnel to grow sales.
  • December 2015 – While trying to heal my knee, I read Unbreakable Runner and learn how CrossFit can help condition you for long-distance runs without spending hours pounding the pavement (a more productive approach to training). I complete an onramp course and quickly develop an obsession with CrossFit and forget all about the running (yep, I’m one of “those” people).


2016 – The side-hustle takes off

  • Early 2016 – I refocus my attention on growing my audience and adding as many people as I can to my sales funnel. I also work with my first few productivity coaching clients in New Zealand and Australia (who have purchased the “Strategy Edition” of my toolkit). I decided that if I’m going to leave my (new) job I can’t just rely on product sales. I need to do some consulting. I aim to earn a minimum of $4,000 per month in order to cover business expenses, pay the mortgage and replace my salary. Hayley and I also make plans to travel around South East Asia for 6 months in 2017. Now I have a deadline to work with.
  • March 2016 – I set up a coaching program to help people with productivity but finding clients is hard work. Perhaps I need a better offer? As an experiment, I list myself as an expert on Clarity and list my skills like Asana, Productivity and MailChimp. I book a call with a client in San Fransisco who needs help with Asana and I think “Great, I can help with that!”.
  • Q2 2016 – I continue taking calls on Clarity and help people with productivity and Asana. I also notice I’m getting a lot of traffic through Google for my book summaries, so I start writing a new ebook, Guidelines, that appeals to book lovers.
  • June 2016 – I decide to double down on the Asana Consulting and position myself as an expert in this niche. It’s a very targeted market, but it pays off. Because I’ve niched down, I’m now being discovered online via people searching for “asana consulting” on Google. I close my first few “fixed price” sales and move away from hourly billing (doubling my effective hourly rate). Hayley and I continue with our travel plans, book a flight to Bali and plan to leave January 2017.
  • August 2016 – Hayley and I decide to sell our house before we leave for our trip and list it for sale.

house ready for sale

  • Q4 2016 – The Asana consulting is going well. For the last few months, I’ve been matching my full-time salary through consulting and product income. I plan my exit from iRefi and intend on finishing up at the end of the year. I decided to branch out and help business owners with other tools like Pipedrive and MailChimp. I also continue with product development on Guidelines, the 7-Day Productivity Plan and the Personal Productivity Toolkit, adding more resources and package options. We manage to sell the house (timing the market perfectly), throw away tonnes of old junk and put our remaining belongings into storage.
  • 16th December 2016 – I finish my last day of work at and begin to freak out about the idea of full-time self-employment.

2017 – Our travel adventure

  • 10th January 2017 – Hayley and I say goodbye to our friends and family and head to Auckland International Airport to begin our 6-month travel adventure.
  • Q1 2017 – I have a moment of panic when we first arrive in Bali. I can’t help but think “What if it all goes wrong?” and “Did we make a mistake by selling the house?”. I quickly start to relax and we spend the first 7 weeks of the year in Bali, Indonesia working about 15-20 hours per week, sunbathing, surfing, doing CrossFit, exploring and earning more than I ever did working a full-time job. We then move on and spend 3 weeks exploring Cambodia and 4 weeks in Vietnam.

  • January 2017 – I meet some amazing folks to the Dojo co-working space and get invited to speak at the Digital Marketing Skill Share in Bali later that year.
  • April 2017 – We spend 3 weeks in Japan (one of our favourite parts of the trip). During this leg, I earned over $11,000 working an average of 20 hours per week.
  • June 2017 – Two days before flying home (after over 5 months of travel) we have a scooter accident in Bali, Hayley breaks her foot and her arm in two places. Ouch… After returning home to New Zealand I started working at the BizDojo coworking space in Takapuna.
  • Q3 2017 – Being back home and without the distraction of travel the business really takes off and sales reach a new level. Hayley tries going back to a “normal job” but isn't happy. Things are going well in the business, so she quits to come and work with me. Now we're 100% self-dependent. As Doc Brown would say, “It's the future or bust”.
  • September 2017 – I launch my new How to become a virtual consultant program to teach people how to build a business like mine.
  • October 2017 – I return to Bali for 10 days to speak at the DMSS conference. I also start eating tonnes of food to put on weight so I can start focussing on strength training.
  • December 2017 – We finish the year strong and have earned more in the last 6 months from consulting than both of our entire annual salaries.

working at bizdojo

2018 – Where are we now?

  • January 2018 – We find out we're going to have a baby! We've always wanted to be young parents and can't wait to start our family.
  • Q1 2018 – I take up golf and surfing. I make a point to take the afternoon off every few weeks to enjoy some flexibility.
  • May 2018 – I get a new personal best Clean of 100kg (the training has been paying off).


Over the course of this journey, there are a few key lessons I’ve learned that I’d like to share with aspiring indie-entrepreneurs.

1. Nothing beats persistence and hard work

As you can no doubt see, my journey from full-time worker to self-employed indie-entrepreneur took a little while. There were many ups and downs and failed ideas along the way.

I can think of times when I spent weeks or even months on an idea that I thought would be a real game-changer, only to have all my assumptions proven wrong.

What I’ve learned is that regardless of what you do, you can create the success you’re after by working hard enough and persisting through these tough times. No matter how many times you fail, keep going. This is probably the most important thing I've learned.

2. Focus on the big rocks

What you can’t see in the timeline above is all the time I wasted on little things that didn’t really matter. Like playing with the colour of buttons on my website or watching webinars that weren't relevant to me.

If you haven’t, have a quick read about the philosopher and his jar of rocks.

The moral of the story and what I’ve come to learn is that you should focus your time and energy on the things that have the biggest impact on your goals (similar to the 80/20 principle). For me, I should have focussed on consulting sooner as this was a quicker way of generating the income I needed to quit my job.

3. Niche down and stand out

I only found success with consulting after I specialised in a specific skill (helping business owners to use Asana) that I already possessed; remember, I helped the company I worked for to set up Asana back in 2013.

I could have tried helping companies with “technology” or “project management” but I didn’t. I chose to help them with the one specific thing I know a LOT about; Asana. There aren’t many people specialising in this skill, which is why it’s easier to get clients and get paid a good fee.

After finding success with this I was able to branch out and help with the other specific tools that I have expertise on.

4. Sometimes you just have to go for it

One of the biggest motivators that kept me moving was the commitment we’d made to go travelling. After we booked our flight to Bali I had a firm deadline in my mind. I thought to myself “I need to replace my income before we leave”. Of course, you don’t have to earn a full-time income in order to go travelling, but this is the goal I set for myself.

By drawing a line in the sand, I worked even harder to make sure I could hit this goal in time.

The great thing about setting a deadline like this is that once I left my job I had way more time to grow my business. Sometimes you just have to go for it and take a leap in order to give yourself the time and energy to grow.


Since going full-time on my side-business I've been thinking a lot about how I can help other people to replicate these results. I know there are a lot of people out there who are in the same boat; who want to quit their job and work for themselves.

The good news is that I have an exciting project in the works… Over the coming months, I'd like to help as many people as possible to create a side-business, earn their first few thousand dollars online and eventually be able to quit their jobs.

Over the coming weeks, I'll be reaching out to ask you to take part and contribute your ideas.

UPDATE: You can now learn more about my new “How to become a ‘virtual consultant'” program here.


Do you have a side-hustle you're working on? Let me know how it's going and share your progress in the comments below!