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Live a Deliberate Life, “Beyond the Picket Fence”

This week, I’m interviewing Chris Taylor, writer, entrepreneur, and speaker, about his first book Beyond the Picket Fence, now available for pre-order. I was intrigued about the message of Chris’s book to live a deliberate life and wanted to know more about what this means for employees and employers, and Chris did not disappoint. I think that his message captures the mindset that many of us (regardless of generation) are drawn to in light of the changing dynamics of our economy and the evolution of the traditional ’psychological contract’ we enter into with our employers. Employees and employers both stand to gain by considering his thesis. I caught up with Chris in Spain via e-mail.

  1. Congratulations on your book Chris! Is it weird to be on the other side of things, being interviewed about your own book, rather then you asking an author questions about theirs as founder of Actionable Books?

Thanks Jane. It’s definitely a different experience, but I’m enjoying having a message to share that I feel so strongly about. I always thought the best interviews I’ve hosted were with people who were passionate about their material, so I’m just hoping that comes through now that I’m on the other side of the proverbial mic!

  1. So, if someone did an Actionable Books summary of ‘Beyond the Picket Fence’, what would the ‘golden egg’ be? What’s the key take away?

I would hope that when someone finishes reading Beyond the Picket Fence, they’re left with the understanding and sincere belief that everything we do is a choice. To thrive in the 21st Century – both professionally and personally – we need to take ownership of our lives and live deliberately.

We have more flexibility and option now than ever before, and that can be overwhelming for many of us. I want to encourage readers to pursue their own version of “the ideal life”, even if that means deviating a bit from the “expected path”, and provide them with the inspiration, resources and skills to do so confidently.

  1. Why do you think the ‘white picket fence’ ideal continues to drive the way so many of us live our lives and approach our careers? Do you think that it’s just groupthink, or individual fears, or is it maybe more broadly embedded in our capitalist economy?

Jane, I think it starts with our education system. Most of us spent 12-16 of our formative years taking direction without question and working to fit into a box that rewarded compliance and rote repetition. We were told “do your homework”, and you had two choices – do it and get rewarded, or don’t do it and get punished. 12 years of that pounded (most of us) into a mentality that we should follow the “normal” path, and that deviating from it would hurt us.

Back when it was a reasonable to assume that we could keep a job at the same company for 35 years, the “pursuit of the picket fence” was a safe path – one that wouldn’t raise eyebrows from your co-workers or friends, and one that addressed our base level needs – food, shelter, security, etc. But fast forward 50 years, and where has it taken us? Divorce rates and employee apathy are at record highs, suggesting that most of us are not happy.

Some people are happy in the “White Picket Fence” model, and that’s fabulous. I’m genuinely happy for those people. I just think it’s naïve to assume that we all want the same thing. As I travel the world and see, first hand, the wide range of lifestyle approaches available, I’m also seeing that the people who are happiest are those who have taken control of the direction of their life, the pace of it and, in some cases, even the geography. They’re doing this despite the fact that it may not be appreciated by certain people in their lives, or may cause friction with the status quo.

  1. Should organizations fear or embrace a workforce made up of individuals that seek to build deliberate lives?

I love this question. A couple weeks back I’d half-jokingly suggested to someone that they pick up copies of the book for every employee in their company. The response was, “No way! I need my people pursuing the picket fence so they don’t leave me!” I’m starting to realize this is a common belief, but it’s dangerously flawed.

I don’t think it is news to anyone in your audience, Jane, that we’re on the cusp of one of the biggest talent shortages of the modern era. With Boomers retiring at a rate far greater than the younger generations can replace them, attracting and retaining top talent is going to get more and more difficult over the next couple of decades. The best of the best are going to gravitate to the companies that provide them with the most opportunity, which includes cultures that encourage them to pursue a deliberate life.

I believe the paternalistic approach to business management – employees blindly relying on their employer to care for them, while employers dole out punishment and reward based on following prescribed behavior – is an antiquated model.

The businesses that I’ve seen maintain high engagement rates and low turnover numbers interact with their employees on a more equal footing. They appreciate the fact that an individual who is actively in control of their own future is more engaged with life and work, automatically providing better output and customer service, and so they work to encourage employees to live a full life on their own terms. We see this in the rise of flexible benefits packages, paid volunteer-days and self-directed work days, where employees are encouraged to work on projects of their own choosing.

These top companies also seem to embrace a paradox of (a) operating with the trust and planning as though these top employees will be around forever, while simultaneously (b) understanding that most employees will move on at some point, and that encouraging conversation around an employees career trajectory (even if it means leaving the company) is to be embraced, not feared or ignored. There is most definitely a level of leadership maturity required to embrace the “deliberate choice movement”, but I believe it to be one of the most important components of retaining top talent going forward.

  1. Personally the ideas of ‘living a deliberate life’ and ‘designing a lifestyle’ really resonate with me. How do you see this concept in relation to the ‘Do what you love’ movement? I’ve been critical of DWYL because in my view it ignores significant barriers and economic realities for most of the workforce in favour of starry-eyed idealism. Can everyone live a deliberate life?

I think that, while well intentioned, the “Do What You Love” movement only examines a narrow slice of living a deliberate life. If you’re actively designing your lifestyle, I would hope that you’re including “what you love to do”, but as you say, there are other factors at play that need to be considered. To be clear, living a deliberate life is not about hedonistic anarchy. In fact, it’s only partially about the tasks and projects you fill your days with, and as much the mindset you bring to each task.

Circling back to the “golden egg”, everything you do is a choice. You may not “love” every aspect of everything you do, but you do it because you’re mindful and appreciative of the benefits that the task’s outcome(s) provides. (Ie. You go to work because you appreciate the opportunity to provide for your family.) If you don’t love the nature of the work, then you can work to replace it with something that does resonate more strongly with you, but you don’t just throw it away because you don’t like a particular project or you have a bad day. That’s a short term, emotional response, and not inline with deliberate lifestyle design.

Of course, if something doesn’t provide real benefit and you don’t love it, then you should take active steps to remove or replace it. That’s what living a deliberate life is all about.

  1. You and your wife picked up and moved to Spain for a year, while you continued to run (and grow) an internationally successful business that you started here in Toronto. I really liked your blog post last year that called out the people who kept telling you how ‘lucky’ you were to be able to do that, when in fact you made some very conscious choices and did a ton of prep work to allow it to happen. I noticed that you also allude to this in the video preview of your book. What were some of the deliberate decisions or preparations you made that allowed this to happen?

Thanks for the question!

First off, we had two false starts, where we’d planned to move at a certain date, and then pushed it out by at least 6 months due to business needs or financial uncertainty. I think a big part of lifestyle design is about that – put your best foot forward, but then roll with the punches.

Secondly, I’ve been very clear – since day 1 with the business – that I wanted to build something that was (1) derivative based (meaning I could sell the same thing over and over), and (2) allowed me to be geographically flexible. To that end, I’ve assembled a team that was comfortable with a high level of autonomy. I’ve had long conversations with key team members about how often I should be back in Toronto, and what the pros and cons are of having me 6 hours ahead of most of our team and clients. My wife, Amy, and I had (and continue to have!) similar conversations about what life would look like in Spain (one example – I often work until midnight to stay accessible to the eastern seaboard).

Those are another two big parts of successful lifestyle design, I believe – (1) steady communication with those it will impact, as well as (2) appreciating the tradeoffs/impact that will come with making deliberate choices – both in a work context, but in regards to life, as well. That comment, “You’re so lucky!” is often followed by “I wish I could move to Spain.” The grass is always greener, as they say and, as much as I love my life here, I’m not sure it would be ideal for everyone. That’s the point though, isn’t it? I don’t believe that anyone else’s life should be the exact model for our own. We need to define what’s important for ourselves, and then work to build that; testing assumptions and taking time for review and reflection along the way.

As an entrepreneur, Jane, I appreciate the fact that I have certain flexibilities that other people might not have. That in mind, I’d also like to share the story of Andy Budgell, our Managing Editor at Since joining the Actionable team 3 years ago, Andy has lived in Vancouver for 6 months, London, England for a year and is now getting set to move to Toronto. He regularly travels to Los Angeles, New York and Paris for his other interests and, with a little forward planning and regular communication, he can do it without shirking his work responsibilities. For context, Andy is an employee of a rapidly growing company with no direct reports. I share this with you because I believe that lifestyle design doesn’t require the freedom of an entrepreneur.

  1. You obviously have a strong belief in the power of the written word to improve people’s lives and workplaces. What books (business or otherwise) come to mind as being especially life changing for you?

As an entrepreneur, Small Giants, by Bo Burlingham was hugely impactful for me. It was a reminder that growth for growth’s sake is blind, and that we need to make deliberate choices in how and why as entrepreneurs we want to grow our business(es).

Seth Godin’s the dip was also massively impactful. I honestly don’t know if we would have made it through the dark spots without the clear message from this little book reminding me that the only things worth pursuing have periods of friction that make most people give up. The rewards go to those who persevere.

  1. What’s next for you?

I’m keeping busy! The business is growing fast – over 100% each year for the last three years, and we’re starting to work with larger clients, which is fun and an exciting growth curve. A big part of the growth is focused on the measurement and study of real world employee engagement, accountability & behaviour change, a collection of topics I find fascinating and increasingly important to organizations of all sizes.

We’re “officially” launching our Consultant Program in Australia in August, which will be my first trip down under, and then scaling up with 4 new North American markets in 2015.

From a lifestyle standpoint, Amy and I are heading off to Panama in November for 4 months of strategy, writing and product development. Apparently, there’s also a family of dolphins that lives in the bay in front of our place down there, so a regular midday snorkel may be in order. I’ll keep you posted 😉

You can pre-order a copy of Beyond the Picket Fence here.

Chris Taylor is a writer, entrepreneur and speaker. He spends his daylight hours helping consultants and employees alike find meaning in their work and discover rich team relationships through his company, When he’s not engrossed in work, Chris is an avid traveler, cyclist and snowboarder who loves nothing more than a well prepared meal paired with a decent bottle of wine and good friends. Chris and his wife divide their time between rural Spain, an island in Panama and Toronto, Canada. This is Chris’s first book.

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