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A few months ago, I wrote a post up on social media sites about how I changed my business from a massive stressfest to funfest over a one year period. While I’ll be sharing that story soon, today’s guests Shannon Ward and Diana Stirling from share their story about big and little shifts they made from their business and life today on the show. Just a couple of years ago they were stuck in their own business (and office building), overworked, ridiculously stressed and hating the business they started even though it appeared on paper that it was “successful”. And now they have changed the game and are inspiring others to do the same. Here is how they did it:

I use RISE partner Wistia for video hosting because they rock. Check ’em out.

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About Today’s Guests, Shannon Ward and Diana Stirling:

Shannon and DianaYou can check out much more about Shannon and Diana and pick up tips, ideas and insights for yourself at and on Twitter @pretirementlife.

And by the way, this is a really cool email Shannon sent me about why they would be the perfect guests on the show:

Here are the Top 10 Reasons to Interview Us for The Rise to the Top:

1. We’re Pretired, meaning we don’t put off living out our dreams until retirement and we’re living life to the fullest NOW!
2. Having children has inspired us to live our lives to the fullest, rather than created an excuse to let go of our dreams (ex. I went skydiving for the first time after my first child was born).
3. We’ve spent more than 13 months living in tropical destinations over the past three years.
4. Our offices have included coffee shops, boat decks, beachfront decks, and even mountain tops. In fact, my current commute is via gondola to the top of Whistler Mountain (site of the 2010 Winter Olympics) and Diana’s office is in a cartoon boat at an amusement park (seriously…see attached pics).
5. We’ve introduced our kids to 6 new countries and cultures in the past 3 years.
6. I discovered a passion for surfing at age 34.
7. We spend an average of 8 months a year in flip flops.
8. We have contributed an estimated $18K to 35 charities in our communities in the past year, and we also give as much of our time as possible.
9. We are a couple of the most tech savvy women you’ll meet and use technology to facilitate our Pretired lifestyle.
10. Through our blog we’re empowering women to rewrite the “rules” of entrepreneurship and motherhood by showing them how to build businesses that create financial wealth, freedom and fulfillment so they can live life now!

This Episode Of The Rise To The Top Is Exclusively Sponsored By HubSpot:

HubSpotToday’s The Rise To The Top episode is sponsored by HubSpot, which wants to help you learn how to use Facebook to grow your business. Facebook is the most popular social network (and I can tell you from experience ALWAYS one of our top three traffic referrers to The Rise To The Top), and with over 750 million users, it can serve as an important marketing tool for any business. Face it: your prospects are on Facebook whether you like it or not. Learn how to start using Facebook to achieve your business goals today. Download HubSpot’s free ebook today at

Bandwidth and Hosting Sponsored By Shopify:

ShopifyShopify makes opening an online story easy. So if you’ve ever wanted to open an online store, now’s the time. Here’s why: The Shopify Build Your Business Contest has over $500,000 in money and prizes. Grand Prize winners will meet and talk with (three former RISE guests!) Tim Ferriss, Seth Godin and Gary Vaynerchuk, plus much more. Also, by entering the promo code “RISE” when you set up your store, you will get two months free (SWEET!).

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  1. Kimberly Appleton says:

    Totally cool what you two are doing!
    I too like to think of myself as Pretired. I’ve just returned to the world of an actual ‘job’ after taking a year of adventure for myself. So fun, so needed. I totally recommend it.
    Working is a part of life for sure – but it doesn’t have to be what defines you.

    Thanks you guys for making my life seem normal.

    1. David Siteman Garland says:

      That’s great to hear, Kimberly.

  2. Bowman says:

    Great interview with two dynamic “pretired” business women! I’d love to hear more from Shannon and Diana.

    1. David Siteman Garland says:

      Definitely. It was one of those convos that could go on about 8485757373 more minutes, hah.

  3. Nataliepreston says:

    You ladies are a constant inspiration to me…well done on another great interview! Keep up the great work spreading the word about living your best life NOW!


    1. David Siteman Garland says:

      Natalie – They rock big time. It was great having them on 🙂

  4. Samtchung says:

    Amazing storey, these ladies are an inspiration!

  5. They are the new Tim Ferris for Women! Awesome Interview! This interview is a MUST WATCH for any female Entrepreneur!….. and the guys could learn a thing or two as well.

    1. David Siteman Garland says:

      That’s a solid comparison. Definitely some similarities.

  6. Maczinger says:

    Thanks for having them on – they are such a great inspiration that women (and men!) can balance families, work, and focus on what is important in life. And that isn’t just money!

    1. David Siteman Garland says:

      Absolutely. Just chasing money = unfulfilled.

  7. sAFETY says:

    As interesting as it was inspiring.

    If you do end up having them on again (please!) I’d like to hear more about the actual logistics.  Selling me on ‘Pretirement’ is one thing, wrapping my head around how to do it is another.  Would love some insight into how I can take the next step from people who have done it!

    1. David Siteman Garland says:

      Absolutely. Will do if I do another show with them!

  8. Matt Avella says:

    Awesome, lots of good info on balancing your business and personal life.

  9. Lisa Fitz says:

    Great job ladies. I love your concept of Pretirement Living, and your story of success. Such an inspiration.

  10. Tracey B says:

    yes, have them back!!!  D and S are so inspiring!!!  pretirement is a gamechanging concept for fulfillment seekers…  you ladies rock!

  11. Gregg says:

    What do they do? How can they help my business?

    1. David Siteman Garland says:

      Did you watch/listen yet?

  12. Brenda Moretto says:

    Diana – you continue to inspire me … I love your passion for business, community and family.  Your pretirement concept shows that if you let your creative juices flow, anything is possible.  Keep up the great work!

  13. Meeganhill says:

    I’m curious to know what their two businesses are now. I know they said that one of them is to teach companies how to buy or sell advertising, but that’s it. It would be great to know how they make their money now and how close or far it is from the million in revenue they had before.

    1. David Siteman Garland says:

      Good questions, Meegan.

    2. Shannon from Pretirement says:

      Hi Meegan –

      Shannon here – thanks for your great questions!  Our company OnTrack Media helps publishers increase ad sales with online/offline strategies.  Our other company, InsiderTrading Group provides turnkey affinity programs for professional associations.  Neither are online businesses, yet we’ve leveraged technology with both in order to create freedom and flexibility for ourselves and our employees & contractors. We are happy to say that we are back to the million dollar mark in revenue as well! Happy to answer any other questions you might have.

  14. LindsayS says:

    I loved this interview! It was nice to hear two women talk about the issues around starting a business as it relates to families and children. I work for a non-profit that is currently “restructuring” to make everyday life for all of us a bit more like pretirement. I think our new economy is going to be based on the pretirement framework and I find that to be fascinating.  I think that we’re all moving into a zone where we plan the phases of our lives and that none of those phases is going to include a workday grind.  That doesn’t mean that we won’t be working hard and getting tons accomplished, but that we won’t exists as hard grinding cogs in someones else’s machine. 

    1. Shannon from Pretirement says:

      Love the cog metaphor Lindsay and that’s so great to hear that your organization is embracing Pretirement related values.  Good luck!

  15. SueB says:

    I love what these two ladies are doing/have done! They have inspired my business partner and I to model our business after the values they have shared with others. Great work ladies!

    1. David Siteman Garland says:

      Fantastic to hear!!

  16. RobertE says:

    Love the pretirement concept…these ladies continue to inspire me to push forward on similar goals. Freedom, work/life balance and the ability to make your own choices are critical to living the dream. Keep it up!!!

    1. David Siteman Garland says:


  17. Jacs says:

    oh my goodness, I am just in love with all three of you!  Thankyou so much for doing this wonderful service David.  I found you from Leonies’ World Biggest Summit.  Hurrah!  So much to go think about!  Thank you all. xxx

    1. David Siteman Garland says:

      Hehe thanks so much Jacs 🙂

  18. Kris de Leon says:

    I love this show, and am learning to build my business in a way where I’m having fun in the process and generating strong cash flow. Thanks for this!

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8 Steps to Turning What You Already Know into a Successful Online Course

The 8 step process to the successful with online courses + free gifts for attending!

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