The Problem With Lifestyle Design


I’m all for getting what you want out of life. Too many people blindly go through the motions without ever questioning what’s really important.

But there’s a growing cadre of ‘lifestyle entrepreneurs’ advocating that you should design your ideal lifestyle before you get started in business. Your business should suit your desired lifestyle, they say, and not the other way around.

Tim Ferriss, in the 4-Hour Work Week, talks about how his supplement company was extremely profitable — but he was extremely miserable. He was making money but he wasn’t actually enjoying the work. Ultimately, he discovered creative ways to automate the business to take himself out of the equation.

But here’s where most people miss the point: Tim Ferriss had a profitable business to automate.

There’s no point worrying about automating your business if you don’t have a business.

The problem with lifestyle design, or building a business with the goal of achieving a certain lifestyle, is that the road to getting there is almost always paved with hard work, risk, and uncertainty.

It’s no easier than building any other kind of business.

And if the only reason you’re in the game is to ultimately sit on the beach and do nothing… I’m not sure you’ll have what it takes to push through when things get messy.

The truth is, the people that have actually built successful lifestyle businesses are extremely driven, worked extremely hard, and probably still do. The difference is now they do it because they want to.

This post is my submission for day 6 of #YourTurnChallenge, a 7-day blogging challenge orchestrated by Winnie Kao, Special Projects Lead for Seth Godin.

Flickr creative commons image via Luke Ma.

Why I Do Not Want to Write This Post


Apparently, shipping is hard.

Today is day 5 of the #YourTurnChallenge, where myself and hundreds (perhaps thousands) of others have foolishly agreed to ‘shipping’ a blog post everyday for 7 days straight.

It’s supposed to train us to get into the habit of releasing our ideas… or something like that. I’m not sure anymore, but it made sense at the same.

Bottom line: I really don’t want to write this post.

To be honest, days 1 to 4 were pretty easy. I had a decent workflow that worked well and didn’t interfere much with the rest of my day.

Here’s what it looked like:

  1. Free write first thing in the morning. I didn’t set a target word count or have a set amount of time. I just wrote until I felt like I had a post. I began each free writing session with an idea that usually either evolved or changed entirely by the time I was done. This took, on average, 15-20 minutes.
  2. Don’t do anything. This is probably the most important part. After getting the free writing done in the morning… I went on with my day and forgot all about it. There were days that I was tempted to release it right away, because I thought it was good. But it always turned out better if I waited and let the ideas sink in.
  3. Polish it up and hit publish. At the end of the day, I’d grab my free writing notes from my writing app and paste them into WordPress. Then I’d read it over and edit, as many times as needed, until it was done. Finally, I’d head to Flickr to find a relevant image.

But that all went out the window today.

I got a late start to the day and didn’t have the time, or wasn’t in the mood, to do any free writing.

I spent the morning spinning my wheels on a task that shouldn’t have taken as long as it did and frustrated the heck out of me in the process.

My frustration carried forward into the afternoon and was followed up by a series of meetings that ate up the rest of the day.

Now it’s almost 7pm, I’m tired, I’ve got a long list of stuff left to do… and I do not want to be writing this post.

But it doesn’t matter. I must ship.

This post is my submission for day 5 of #YourTurnChallenge, a 7-day blogging challenge orchestrated by Winnie Kao, Special Projects Lead for Seth Godin.

Flickr creative commons image via Andy Blackledge.

What happens when you only listen to half the story

This morning, I cued up a Mixergy interview with Noah Fleming for listening during my kettle bell workout.

Noah’s story is interesting — and the interview covered some inspiring anecdotes from his journey as a marketing consultant, and now author.

For example, Noah told the story of when he hosted a free breakfast for a group of high profile CEO’s at the Four Seasons in Toronto. He booked the venue, paid for the catering, sent out invitations to a large group of CEO’s, and hoped some of them would show up.

That sounded crazy to me. How can he expect a bunch of busy CEO’s that don’t know him to show up to a breakfast just like that? It’s not like the free breakfast alone was going to entice them.

Apparently, Noah felt the same way. He described how all his self-doubt and anxiety surfaced as he stood in the hallway of the Four Seasons at 6:40am wondering if anyone would show up by 7:00am.

In the end, he had a full house. The breakfast was a huge success and it generated tons of business.

But it’s stories like these that people misunderstand.

It’s tempting to conclude that the breakfast was a big win because Noah had the guts to get out there in front of some big CEO’s and make a good pitch.

He took an idea that would’ve been too daunting for most people and executed flawlessly. Feel good story of the year.

But if you listen to the rest of the story, you’ll see that what Noah did was far more nuanced than that.

  • He had been building his email list for years. Every week, he was putting out high value content that people were starting to notice.
  • One of the CEO’s who attended the breakfast was on his email list. And his invitation included a testimonial from that CEO, who was a recognized name among his peers.
  • He already had a full roster of clients that gave him the experience to speak to his topic with credibility and authority.
  • He was in the process of writing a book on customer loyalty, and he shared some of the highlights from the book with that group of CEO’s.
  • He was coached and trained by Alan Weiss, one of the world’s most famous and prolific business consultants.

In other words, he didn’t build his business by making high stakes pitches to CEO’s. He put in years of hard work leading up to that moment.

The problem is, if you take that story in isolation… it sounds like Noah was an overnight success. It sounds like that breakfast was how he really ‘made it’.

I’ll admit, I was tempted to call up for the Four Seasons to schedule a breakfast of my own. I was already writing the copy for the invitations in my head.

Then I heard the rest of the story.

This post is my submission for day 3 of #YourTurnChallenge, a 7-day blogging challenge orchestrated by Winnie Kao, Special Projects Lead for Seth Godin.

My 3 Words for 2015


Okay, I know it’s almost the end of January and I’m late on this one.

But better late than never right?

Chris Brogan started this exercise back in 2006. Instead of coming up with a long list of new year’s resolutions that will likely be forgotten (and likely are forgotten by now)… he recommends picking 3 words to frame your goals and intentions for the year.

Here’s why I like the approach:

  • It requires minimal planning. I feel like I’ve already wasted so much time planning in my lifetime that I can’t afford to do any more of it. Having a strategy and thinking through what you want to achieve is one thing… but sitting down and day dreaming about the future at the expense of taking action is a trap I’ve fallen into more times than I care to admit. The 3 words idea cuts right through the non-sense and gets to the point. I like that.
  • It’s easy to get down on paper quickly. I am obsessive about writing things down. If I think of an idea, or something I need to do, or have any kind of musing… I immediately need to write it down. This can be a productive habit if you stay within some healthy boundaries. I exceeded those long ago. This is one of the reasons planning scares me… more stuff to write down and put somewhere. 3 words is music to my ears.
  • It’s easy to remember. I’m probably the only one still thinking about new year’s resolutions. In fact, I’m sure most people have already forgotten what theirs were and have fallen back into old habits by now. But 3 words is simple enough… if I ever feel like I’m off track, I only need to recall 3 simple words, or read this post, to remind myself where I’d like to be and what I should be doing.

Here are my 3 words:

1. Work

I’d like 2015 to be characterized by a large volume of work. I believe that the path to mastery, in any endeavour, is about putting your head down and doing the work. There’s no substitute, no shortcut. And I don’t think I do nearly enough of it. The key here is to do ‘real work’, not ‘busy work’. There’s a lot of stuff I do that feels like work. But is it really pushing the ball forward? Not so much. That has to change in 2015.

2. Ship

The list of stuff I’d like to work on gets longer and longer every year. I’d like for it to get shorter in 2015. It’s time to start chipping away at that list by identifying which projects are worth my time and pushing them forward relentlessly. The hard part, I think, won’t be the act of shipping itself… but deciding what to ship and what to keep on the shelf.

3. Slow

I tend to abandon ideas too quickly. It’s the lizard brain, or the resistance, doing its work. I get impatient when I don’t see results right away. But things that are worth doing often require you to lean in, trust your gut, and be patient. I need to discipline myself to slow down and let things materialize instead of running off to the next shiny idea.


Looking at it again, there’s a lot of overlap there. But I’m working towards a deadline here…

This post is my submission for day 2 of #YourTurnChallenge, a 7-day blogging challenge orchestrated by Winnie Kao, Special Projects Lead for Seth Godin.

Flickr creative commons image via clement127.