Shannon Ward & Diana Stirling are a unique duo that are striving to use their business On Track Media, to build “Pretirement Wealth”, which includes both capital AND the time and freedom to enjoy it.

Shannon and Diana living the dream
They also are determined to ensure that they and other women entrepreneurs are building businesses that support their ideal lifestyle.
They have worked hard, fallen hard, and risen from the ashes to tell the story of how they went from their “dream” business with $1m in revenue to fulfilling lifelong personal dreams while succeeding with a new business model based on a very different definition of success.
Diana recently returned from 4 months in Australia with her family and Shannon from a 2 month “learn to surf” trip in Costa Rica with her family.
It was around this time that I had the pleasure of meeting them and engaging in an energetic and lively conversation about how they’d totally changed their lives to achieve the lifestyle they wanted. I drilled them with several questions as I knew this was precisely what I was about to embark on and that they’d have some fantastic advice for me.
And they did. Here it is in both in video and below in writing. Enjoy
When you initially went into business what did you want to achieve?
Shannon: I wanted to build a large business. Big equaled success at the time. $1M revenue, 15 employees and a large downtown office. It was the only barometer of success we had ever really been exposed to at the time.
If you could pass on one key lesson learned when setting up your business what would it be?
Diana: Make sure you take the time to build your foundation: Legal, Insurance, Taxes, and Finances. At all times know your cashflow – cash is KING. You don’t have a business without cash.
What was the turning point that made you decide to downsize and live life to the full?
Shannon: I walked into the downtown office when we were at the height of our revenue and number of employees. Diana looked at me and asked what was wrong and I just started to cry. I was desperately afraid to admit to her that this definition of ‘success’ was not working for me.
We were working 80+ hours per week, we were exhausted and never saw our families, and we were no longer engaged with our clients – we were spending our time with HR issues, legal consulting and accounting meetings.
In one frank conversation, we knew were on the same page – Diana was losing precious moments with her newborn son – and also dreading the business that we had poured our passion into.
We knew we needed to start valuing our TIME more than any other success factor. It was at that point that we restructured everything to become PRETIRED – to have the capital and the time and freedom to enjoy it with our families.
Your both living what many would consider the ideal lifestyle, what could we all do tomorrow to be one step closer to it?
Shannon: The step before that even is to figure out what really matters to you. This was harder for us than we expected. We were so caught up in roles and expectations of who others thought we should be that was difficult to identify what really mattered to us and what we really wanted out of our lives.

Diana jumps into her great lifestyle
Add business and family commitments, a mortgage and a dog and it becomes challenging to see beyond what everyone else needs from you and focus on what you want and need. Once you know what you want start building your life (not just your business) to accommodate that. It’s taken us over 2 years of conscious work to get to this point.
Tell us your key advice about how to build and maintain a healthy working partnership
Diana: Your business partner is like your spouse without the makeup sex. Like any marriage, it takes work, communication and a solid knowledge of your financial situation at all times.
Shannon: Especially when you are working on the other side of the world from someone – you must communicate well so you can be sure you’re both working toward the same goals. At the same time you have to trust that they are doing their thing and working hard even though you can’t actually see them everyday.
How long did it take you to become profitable enough to support your lifestyle?
Diana: As long as it took us to realize that it wasn’t all about money…
Shannon: The two key factors are money and time together. We could be making a lot more money but not have the time or flexibility to live out our dreams. We’ve learned in the past couple of years that we need a lot less money than we used to think to be happy.
How did having children change your perspective on your business and priorities?
Shannon: Having my son changed everything. It changed where I wanted to work (mostly at home), how I wanted to work (with enough flexibility to spend lots of time with my son and husband during the week) and what I wanted to work on (any time spent working was now going to take away from time with my family and so it had better be rewarding work that fulfills me or it’s just not worth it so much anymore).
Diana: Having children immediately shows you how fast time goes – your child is an infant for less than 6 months… that’s less time than it takes to launch a product. Don’t put off living and experiencing any longer.
If you were to suggest the three main tools you need to be able to work and travel what would they be?
1 – Salesforce.com
2 – Google docs
3 – Skype (Shannon managed a team of 5 people when she was living on the beach in Costa Rica – all through Skype)
What are some of the top books you’ve read that have made a personal difference to you and influenced you and why?
The Four Hour Workweek (4HWW) by Tim Ferriss, after reading this we defined Pretirement. We could write forever on just the principles we learned in 4HWW but these were our “ah-ha” moments.
- Introduced to “Deferrers” those that save it all for the end, only to realize life has passed them by.
- Everything popular is wrong! And retirement is WORST case scenario insurance!
- Sell or donate all the clutter in our lives – FREE ourselves!
- Process and outsource!
What is your key piece of advice to anyone considering a location independent business
Shannon: Get out of your own way. The first time especially, it can be downright terrifying to cut the ties and attempt location independent work. However, there are numerous books and blogs for advice on how to do it, and most importantly the technology now exists to support it. So, get out there – there is no excuse not to in this day in age.
Catch the ladies new blog here www.pretirementliving.com
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