TMBA 252: Do We Need to Re-Train Ourselves to Enjoy Free Time?

TMBA 252: Do We Need to Re-Train Ourselves to Enjoy Free Time? post image

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We’re getting into some advanced level stuff this week. As entrepreneurs, many of us have achieved what we’ve built by putting in insane amounts of hours on the phone or behind the laptop. How can we re-train ourselves to step back and enjoy what we have been working for? This week, we’re outlining 5 different ways to go after some meaning with that time that you’ve been creating.

Listen to this week’s show and learn:

  • What the “Sharing Economy” has changed about how we work.
  • Why we should be trying to own our time.
  • The differences between working 24/7 and treating your business as a craft.
  • How to clearly define what the best things are to do with your time.
  • Why taking care of your body is just as important as taking care of your business.

People on this episode:

Mentioned in the episode:

Talking Business with TMBA Sponsor Sean and Current Apprentice Grant

Talking Business with TMBA Sponsor Sean and Current Apprentice Grant

Listening options:


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Dan & Ian

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Published on 07.10.14
  • Great episode, as always.

    Here’s my two suggestions:

    a) learn to play an instrument; and then join a jazz band. Once you get into it, you’ll never worry about having too much free time again, there’s always something else to learn.

    b) take up running. You don’t need to be an athlete; in fact, I reckon it’s more fun if you never were. The buzz you get from getting a Personal Best as you get older, while the more experienced folk only get slower, is awesome.

    And the best thing? you don’t need to wait until you get to be successful to do these, they’re both really good with keeping you sane on the journey :)

    All the best
    Rachel from Scotland

    P.S. Jazz? It’s that form of music that’s like rap, but with added tune, harmony and some variation in rhythm :)

  • Wanted to make sure I commented on this one. I think you guys sold it short as a “301” episode, for the simple reason that everyone new to this space is wondering what “success” looks like. It’s damn confusing to have the Tim Ferrisses saying it’s all about lifestyle and the business should serve that and the Mark Cubans and Gary Vaynerchuks saying if you have time to sleep you’re not working hard enough. While I think you made crystal clear last week that everybody needs to run fast enough to get off the runway, it’s worth keeping in mind even for newbies that there are multiple incarnations of “success”, not least so we’ll know what to shoot for. Continue to love that you guys operate in the space between assumption and reality, a space in which only real practitioners can hatch insights.

  • Ian, same reason I always find myself working as well. When I’m not working there’s some guilt kicking in and it makes the times when I’m supposed to be relaxing INFINITELY more difficult.

    I spent a week in Palawan last month and it was amazing but awful at the same time. The itch to just check my emails was almost unbearable. I kept wondering what’s going on back in the biz world.

    While doing things that were supposed to let me relax and have fun, my mind kept going back to “I should/could be working right now.”

    And I wouldn’t have it any other way.

  • Cherry

    Tired of work this week badly, and just feel dizzy

  • Cristina C. Ansbjerg

    I’m looking forward to listening to this episode. I’m the kind of person who tends to experience guilt when I take some time off. I even feel guilty when I decide to stop working earlier one day. And reading fiction should always be a pleasure…I may have lost my ability to enjoy it (sad face)

  • TJ

    I definitely identify with the craftsman mindset. It was interesting that you mentioned Jiro Ono. Though he is focused on his craft, his sons are more focused on the business. They just announced the first overseas sushi restaurant to open in Beijing.

  • Great episode, and thanks for the shout out – very much appreciated!

    Really interesting topic. I think one of the hard things about this is that people who are more likely to build successful businesses are also the people who really enjoy the process, the hustle, and watching something grow. There’s something addicting in the pursuit itself.

    So once you do get to this point, trying to wean yourself off your business can be tricky for a lot of people even if it’s setup well to run on it’s own. That same hustle and determination that allowed you to succeed in the first place will continually be pushing you to take things to the next level, grow further, etc, etc. – making it harder to step back and simply enjoy the fruits of your labor.

    So a tricky thing to accomplish, but definitely a worthwhile pursuit. Again, great episode guys!

  • Seth Overly

    “You ain’t gonna be doing no business when you’re dead.”

    This is a really interesting topic. Nate makes a great point
    in that this can also apply to those starting out and what they envision
    success to be. There’s a lot (often times conflicting) advice on how to get to
    success but not a lot of information as to what the hell to do once you
    actually get there. The idea of stepping back and really getting clear on your
    vision at that point, of you want the future to look like and what you want to
    affect seems like it would be a critical step. Personal health and
    relationships would also seem to be important things to focus on.

    The idea of having a craft is also intriguing. In way, it’s
    using the love of process, growth and improvement and implying it to something
    you’ve always wanted to do: master an instrument, language, other skill, etc.

    Helping other people and the joy that comes from that could
    also be a great antidote to guilt for “not working”.

    Good stuff.

  • Great episode guys.

    I’ve been chewing on something Ian said about not considering himself the CEO.

    That’s cool, call yourself what you want, but I think your frame of reference is off a bit. To me the CEO moniker is not about how many people you employ but how do you see your role in the organization.

    Are you just the chief technical officer, salesguy, product expert, etc. OR are you a leader of leaders?

    Even in a flat organization are you hiring people that are/or become subject matter experts in their sphere of responsibility and allow them to shape your business? or are you hiring “bodies” to do your bidding.

    I know your business a tiny bit and am pretty sure it’s the former, not the latter. So I think CEO is fitting.

    My two cents.

    DT – Founder & Chief Executive Officer of Linchpin


  • Agota Bialobzeskyte

    Here are some things to consider (the “you” there is general “you” not aimed at Dan or Ian personally):

    1. What’s your number? I think all entrepreneurs who have any ambitions in life besides building businesses and making money should know what is the dollar amount that would make them say “Okay, I have enough, let’s move on to something else now”. Would you need 1 million to retire? 10 million? 100 million? There will always be more money to be made so if you don’t have an “enough” number in mind you will always feel like you “should” be working more.

    Related to this point:

    2. Why do you place such importance on things that make you money? We are socially conditioned to think that “work” (aka making money) is important and “play” (aka something you enjoy but don’t benefit from financially) is not. Yet, if you are at the point where you have the financial freedom, is that really true? Assuming that you are well-off already, why would things like playing a guitar or learning maths or learning a back-flip be less important than making the money you don’t really need? This is yet another manifestation of a bizarre trend of fetishizing money (thinking that money is not the means to an end but an end in itself)

    3. Why do you assume that there are only two options:

    a) Make money.

    b) Sit on the couch and watch “Desperate Housewives”.

    I will never understand this one. It seems that people have their identity so closely tied to making money that once you take that activity away they are completely lost. Well, what about getting to your “enough” number, then dedicating yourself to arts, sciences, social work, whatever? There are plenty of unprofitable but important problems to solve (you are good at marketing? why don’t you go and get more sponsors for that homeless shelter?).Yet once again we come back to “unprofitable” = “unimportant” line of thinking.

    Here’s an example of unprofitable problem – how many problems like this would be solved if entrepreneurs would know when to say “Enough” and move to bigger and better (and less profitable) things?

    These points are aimed mostly at those who see building and running a business as means to achieve financial independence not as an end in itself.

    Also, about the “need to be busy all the time” issue, I think it’s largely emotional masturbation which should be recognized as such and not taken seriously. People who “work all the time” rarely work as much as they or others think they do and more often than not produce subpar work. Yes, this constant “busyness” makes them feel good about themselves and look important in the eyes of others, but is it the best way to get results? No.

  • thisjungle

    hey gents great podcast once again …. two words “GO SURFING” (game changer)

  • I really needed to hear this today. Early retirees have the same problem. Go at it real hard for a short time, now ALL this extra time.

    After year, I’m finally letting myself off the hook for not doing anything. I’ve taken up a bit of the athlete approach. I’m training for a marathon now.

    For those of us who were too busy working to have any fun can start dabbling with hobbies. What did you want to do with all that time when you were working so hard?

    As in…”When this business takes off, I’m going to _______________.”

    What was that blank?

  • Agota, I wrote my comment before reading yours. You are EXACTLY right. If financial freedom was the end game, what’s “your” definition of it? How much is enough?

    I know that number. I got it. Last year, I left corporate.

    And for the year, I found myself caught up in busy-ness. I’m not even that type of person. But, I just had to have some major project.

    Now, I’m realizing that it’s okay. The rat race doesn’t exist. It never did. I was creating it. NOW, what do I want to create?

    The laziness voices are real and internal, but once I figured that part out, I was able to relax and start enjoying what I created in financial independence.

    (And yest, I am still called to cultivate the Working Mystic community.)

  • jgf80

    Hey Dan and Ian,

    Just come across your podcast a couple of weeks ago and really getting into it, it is refreshing hearing a podcast that isn’t selling something about selling and actually from real experience.
    I am trying to download ALL of your episodes back to number 1 so I can just go through them as I please, but only the past 25 or so are available on itunes and I can’t seem to find the download links to download and listen offline.
    Are you able to put up a table of all of the links to directly download them? Or if you don’t want it displayed publicly, would I personally be able to get the links?


  • Wow great comment, I really love Nathan’s approach above, that’s so rare in the entrepreneurship blogosphere and I think a healthy/interesting experiment.

    I also totally agree a huge problem comes in when money becomes an end, even I would argue in businesses, it causes people in many business contexts to make bad enterprise decisions and can also result in boring businesses.

    Great comment! and thank you for the links

  • The number part is very difficult for me, I’m not sure it works for me to declare a number and then race there. Not sure why….

  • Hey John when you subscribe anywhere on the site it sends you this link:

    Thanks for listening!

  • thanks for listening!!!! I very much enjoy filling in that blank :D

  • haha :D

  • cheers man! I actually reject it from just a taste point of view, I think it’s cheesy

  • thanks Seth! i agree when starting out if you can imagine what success might look like (which is surprisingly easy and cheap to do!) you’ll be way ahead of the game… it would suck to work 5, 10,20 years for something that you could easily determine you never wanted in the first place (say, moving to florida and watching TV reruns).

  • Cheers Andrew!!! that which makes us strong can also be our weakness!!!!

  • very interesting! thanks for the link

  • :D

  • :( This work guilt thing is endemic amongst TMBA readers :P

  • thanks Nate appreciate that feedback!!!

  • hey Rachel love the add music into your life thing. And if you do take up running, as I have and love, make sure you work out those IT bands or else your knees and hips won’t be thanking you in 15 years!! :D

  • Ian

    Welcome John! Thanks for swinging by and let us know if you get through them all!

  • Ian

    I agree with the mindset ideas here DT. I think somewhere either through hollywood or silicon valley or seeing those three letters on various twitter profiles I’ve just become uneasy with it.

  • Ian

    Kinda agree on this point Vincent. It’s a strange phenomenon that is probably going to take several years if not a lifetime to flush out for me!

  • Ian

    Ok Rachel, we meet again… I remember you from itunes… thanks so much for the review! Fun fact: I used to play a brass instrument in another lifetime. Respect for the jazz!

  • jgf80

    Thanks for the link Dan, I overlooked it.
    And keep up the good work guys.

  • Zane

    Love this topic guys.
    I just started a project that’s going to get me where I want to be (which is similar to
    where you guys are) and I’ve got to say, it’s ridiculously overwhelming.

    Right now it’s hard to enjoy a lot of the things that I used
    to be able to enjoy, like reading or spending time with friends, without being
    like “Man I should be working right now.”

    But you’re right, I got in this as a means to happiness, not
    wealth. So while it’s great to hustle and get after it, I’ve got to take a step
    back and enjoy life when I need it.

    Keep the awesome stuff coming guys!

  • Dan Andrews – CCO Chief Coconut Officer

  • Yeah enough wankers calling themselves CEO of a 1 man show will do that to ya.

    Ian Schoen – CCO Chief Cat Officer

  • LIKE

  • cheers Zane pumped it resonated for ya, I feel ya on the guilty stuff… that’s part of the reason I focused on the parts of my business that really interested me and that I felt like brought me (as well as the business) growth

  • This story is about and old friend that I think is relevant to this discussion of business vs lifestyle. There’s an old friend that has drastically influenced the career path I have pursued. The popular Entrepreneurial platitude “Entrepreneurship is living a few years of your life like most people won’t, so that you can spend the rest of your life like most people can’t.” did NOT work out for my friend…

    I will call my friend Yuri (not his real name) and he was a Russian immigrant. I’ve always thought very highly of Russians and people from Eastern European cultures. They are very direct and aggressive but at the same time they are very loyal and they are also very hard working people.

    I met my friend Yuri at the end of my last year in high school, he was about a year older than me, and I was very impressed by him. At 20, he was a top performing sales person at a car dealership. He was always happy to buy his friends dinner or buy everyone a round of drinks, he was tall, handsome, wore nice clothes, a nice watch and drove a nice luxury sedan at a time when most of friends drove old Honda Civics. I remember him being a street, social and business savvy young man. Yuri even had big plans to one day open his own car dealership and go into business for himself. Yuri was a winner.

    Upon graduation I really didn’t know what I wanted to do, I was sick of being a waiter at restaurants and I had no idea what would be a worthwhile college degree to pursue. I decided I should try doing the same thing Yuri did for work, he gave me some tips for nailing an interview as a car salesman. Which I applied and soon after graduating high school I had a very serious job as a car salesman at the busiest Toyota dealership in my state. This put me on the entrepreneurial career path.

    Yuri soon left the car business for the (at the time) booming real estate finance business, where he did even better. He got me a job at a finance firm where I advanced quickly and continued to grow my sales and deal making skill sets. We had a very active social lives, Yuri smoked plenty cigarettes, drank daily (like a good Russian!) and partied hard (like a successful young man does). We where having a great time; working harder and playing harder than anyone we knew.

    As the boom times in the real estate finance business subsided, I began my career in corporate America. Yuri was promoted at his brokerage and got a greater workload of increasingly difficult to finance deals to manage. Yuri spent arduous long hours in the office trying to save finance deals as the 2008 financial crisis was growing. We still partied quite a bit as Yuri had a lot of stress to blow off from work.

    After several years in corporate America I cashed out my 401K investment portfolio, fired my boss and went to into business for myself. Around the same time Yuri suffered a long due burn out from the stress and quit his job.

    Unfortunately this story doesn’t have a happy ending.
    Years have past and Yuri now lives in a crappy apartment in bad part of town, he never opened his own dealership or started his own business, he can’t hold down a job for more than a few months and he got 2 DUI’s (serious drinking and driving penalties). From time to time I still spend time with him but my old friend is gone. He’s antisocial and kind of a buzzkill to hang out with even though he’s blackout drunk. I’ve also noticed that he’s very forgetful of things.

    Why does this happen? Why does a smart, hard working person become a loser in their career? Someone might say he made some bad decision in business, but bad decisions are an inevitability of business. His current sate is a result of his complete mismanagement of his brain health. Over the 8 years I’ve known Yuri he has:
    – Drunken heavily.
    – Works out very inconsistently.
    – Smoked lots cigarettes.
    – Worked very hard in a high stress deal making environments.
    – Ate plenty of fast food, junk food and cheap food.
    – While Yuri had very challenging jobs, he never really pursued intellectual – –development outside of his workplace.

  • Haven’t listened to it yet – I have my own “inconveniences” at this stage.

    But, my recommendation is: fall in love. Or write – something irrelevant to your business. That’s my line of thinking, at least. You can be creative with it.

    And yes, it can take time.

  • Cristina C. Ansbjerg

    Waiting to have a successful business to take care of your body is making the exact same mistake as waiting to be old to retire and enjoy life.

  • absolutely!

  • really appreciate you sharing!!!!

  • Thanks for taking the time to write this out.

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