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Interview with Pretirement Entrepreneurs Diana Stirling & Shannon Ward

Tell us a little bit about your businesses and how you got started.

We founded our first company, OnTrack Media, in 2003. We worked hard to build a successful marketing agency, growing the company to $1M in revenue by 2006 with over a dozen staff and a stable of great clients.

This should have been a great time in our lives.  We had worked really hard and our efforts had finally begun to pay off. We were, by most accounts, successful entrepreneurs.

We were also mothers (or in Shannon’s case were about to become so). I had a one year old at the time and both Shannon & I were pregnant (and due only 3 months apart).

On the outside it looked like we had it all.  On the inside, though, things weren’t quite so rosy.

We were working 60+ hours a week. We spent very little time with our families and had been feeling burnt out for quite some time.  Adding pregnancy only aggravated the situation. There was no time off, and we thought that was okay. With a newborn at home I was commuting over two hours a day. Our best story was that the day I gave birth to my first child, Shannon was into the hospital within 2 hours with papers for me to sign as we incorporated our 2nd company. (I mean, come on, how on earth could we be proud of that and why were people impressed by that??).

The problem was, we were busy living the lives we dreamed about BEFORE we had children. And, of course…as we all know, children change everything.

You both work from another part of the world for 4 months every year, how were you able to do this?

One day we realized that our lives weren’t working for us anymore.  Thankfully, we also realized if it’s not working  – we had the power to change it. What we built we could tear down and rebuild. But it took developing a radical redefinition of success. Our new definition of success wasn’t $1M in revenue and a beautiful downtown office. Our NEW definition of success was to be Pretired which meant:

  • Time first & money second
  • Freedom & flexibility to live our life
  • Enjoy the time when our children are young

We now live what we’ve coined a Pretired Lifestyle (because it’s new and wasn’t defined). It means living a retired lifestyle while we’re young and not putting off the things we want to do until we’re 65. An important part of Pretirement for us is traveling the world with our families, and so we make it a top priority.  We use our businesses to build “Pretirement Wealth”, which includes both capital AND the time and freedom to enjoy it.

Do you think you can take your business to the “next level” living the Pretirement lifestyle?

Now we pursue evolution rather than growth in our business. We define business success in terms of how well it is serving our needs related to our Pretirement. So to us, taking our business ‘to the next level’ means continuing to ensure our business meets our personal definitions of success: that it continues to enable us to have freedom and flexibility, it is profitable and utilizes the best resources, and that it helps us to contribute in a meaningful way in our communities.

Our business is more profitable today with one full time employee than it was with 13. We have learned that size truly does not matter and is not necessarily a great indicator of success.

How long did it take you to make these changes to your companies?

It took us two years to make these changes (some were faster than others) and we’re still learning and refining! That is why we started PretirementLiving.com – so that we could share our tips and experiences along the way. We are hoping to build a community to start a conversation about challenging the current status quo for working moms. We hope others will be inspired by us and others in the community to redefine success in a way that fulfills them in both their work and home lives.

How many hours do you work a week and how much is spent is your home office?

It depends on the time of year! The amazing thing about Pretirement is that our new business model is based on a Results-Only Work Environment (ROWE). There is absolutely no expectation at OnTrack of core hours, face time, or even vacations.  Everyone in our company lives the core Pretirement values of working where and when we want. Pretty much anything goes as long as the work gets done.

How would you rate your success from 0 – 10?

The most important lesson we’ve learned, is that success is NOT determined by anyone else but YOU. Success is something that no one can tell you how to do and Pretirement is just a part of the overall picture.

What we can tell you from our experiences over the past few years is that we had lived our whole lives defining success based on other people’s terms – whether they had been our colleagues, friends, families, competitors or society as a whole.

When we started to truly define our success based on our own terms, that’s when really cool things started to happen.

So today, we would rate our success as a 9 or 10, though, on the outside we may look less successful than we have in the past! The key is to let go of other people’s expectations and to  stop worrying about what others think.

How do you manage all of your personal and business activities?

To start, we’ve banished the term balance from our vocabularies and now focus on creating fullness in our lives instead. At any time one part of our lives may be ‘tipping the scale’ and that’s what creates fullness. Fighting to make sure we have ‘balance’ at all times between work and personal is a recipe for disaster. We can’t do it, and more importantly we don’t want to.  Balance is not a requirement in our lives anymore.

What has been your biggest business struggle as an entrepreneur?

Perseverance and Persistence. The realization that we have the ability to change our businesses to meet our goals, even if those goals change. Entrepreneurs are the most resilient, strong and passionate people I know – we truly can do anything! Some days, when we’ve had a disappointment and are trying to motivate ourselves, we need to remind ourselves of that!

What advice would you give to a new entrepreneur?

We didn’t know this at the time, but looking back we’ve learned that when you build your business you should also build a Pretirement plan. With a Pretirement Plan you can define not only your business goals, but also how those goals will be integrated into your broader life.

A Pretirement Plan should answer three core questions:

1) Define what Pretirement looks like for you: for us this was traveling for extended periods of time, for others it may be three day weekends or weekday time flexibility.

2) Define what success looks like for you: be careful to define success on your terms NOT someone else’s.

3) Define what you’re willing to do and not do to achieve that success: are you willing to say ‘no’ to a client that doesn’t fit within your new business model?

Oh, and Cash is king. You don’t have a business without cash – pay attention to your profit margins and create monthly accounting reports so you always know your cash flow!

For more information on Shannon Ward and Diana Stirling please see: Pretirement Living, follow their tweets on Twitter @pretirementlife or check out their Facebook Page – Pretirement… retirement living in your 30′s!

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One Response to “Interview with Pretirement Entrepreneurs Diana Stirling & Shannon Ward”

  1. 1
    tracy bech says:

    YES: focusing on fullness, not balance!
    great interview – thanks!!

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