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After the podcast ends, we usually do a little “after show” segment following the music.

Community members enjoy an additional live bonus segment called the “after after show”. It’s typically more laid back and low-key.

The recording you’re about to hear came from an “after after show” conversation that went long. It went nearly 30 minutes. We weren’t originally planning on releasing it publicly, but it was such a deep conversation that I really wanted to share it.

It’s about taking a step back. In this off-the-record conversation, I get real with Ben about the challenges of producing as much content as we do. It was right before I was about to take a sabbatical week and you can tell I really need one.

I conjectured about what I might be able to accomplish if I stopped doing all of my shows and newsletters. If I stopped podcasting and publishing daily videos, what might I be able to do? It’s not so much that I want to stop, in fact I really enjoy the work, but more that I’m not sure I’ve had the chance to take a big enough step back to evaluate what it might look like.

I talk about the possibility of taking a whole month sabbatical instead of just a week every seven weeks. Ben and I discuss my plans to take a full year sabbatical in 2020.

The conversation delves deeper into the meaning behind satisfaction, contentment, and fulfillment. I wonder how much of my efforts should be allocated to accomplishing my 5 and 10 year goals and how much should be dedicated to the short term.

I hope you enjoy this behind-the-scenes episode.

Show Notes
  • 01:56 Sean: I’m trying to think big picture here, Ben. What if I didn’t do the podcast, I didn’t do Lambo Goal, and I wasn’t doing seanwes tv? This is my life. If I push all of that aside, what could I do? What am I capable of? I try and be really efficient in my output and time management, so I get the work done and create these pockets of focused time for doing extra things like courses or planning conferences, but what if all of that was aside? I don’t know. I haven’t thought this all the way through, I just got that far. This is not to say that I would stop. I just wonder.
  • 03:03 It kind of led to me thinking, “What if I had a medium scale sabbatical and took off a month?” I don’t know if that would be every seven months or what, and I’m not saying I want to do that. I just started thinking about it.
  • 03:21 Ben: A month every seven months wouldn’t be bad.
  • 03:25 Sean: I would still be producing more content than most people. You can’t complain too much. When I get my back against the wall, like last Friday, I wrote and we shot a seven-part series for seanwes tv. Edited down, it’s between 7,000 and 8,000 words. I did that in a day. I wrote and shot the whole series in a day. That’s close to 8,000 words, and a lot of books are 30,000 words or 40,000 words. I should be able to crank out three books in a month. I should have books, Ben.
  • 04:11 Cory: You haven’t written a book?
  • 04:13 Ben: When was the last time you took a step back and looked at all of the things?
  • 04:29 Sean: I get glimpses of it, like when we went to San Fransisco. You get away a little bit. Honestly, it was July of 2014, and that was when we took a two week trip on the west coast. We road tripped from San Fransisco to Seattle. It took three or four days to unwind, and then I had that much time to really think about things. That was before I did Small Scale Sabbaticals. I don’t know. I do want to do this, full sabbaticals, where every seven years I take a year. That’s 2020. I plan to do that. That doesn’t mean that I won’t do videos or podcasts—I don’t know what it looks like, but I do know that I want to take it.
  • 05:30 Ben: Would it be possible to record enough extra material to where your output doesn’t change for that entire year? You’d probably need to scale it back.
  • 05:42 Sean: I’m not too worried about the output, though. When am I going to do some of the bigger stuff? Should I get up earlier? I need to do that. I was able to crank out 7,000 to 8,000 words in just those few hours. I thought, “Man, I could do some serious damage if I had the focus.”
  • 06:19 Ben: It would be easier for me to talk about it if I knew what the big things were. There are a lot of things, I guess.
  • 06:31 Sean: There are a lot of things. Maybe that’s half of it. There are things that I know I want to do, but there are probably things that I don’t even know that I would want to do because I haven’t given myself the margin or time to explore it. You can probably tell that I’m really ready for a sabbatical. This will probably carry over next week. I’ll do some thinking. I’ll let you know how it goes, Ben. We’ll have a meeting next Monday after the Sabbatical.
  • 07:07 Ben: Everything’s going to change.
  • 07:09 Sean: It’s what happens in December. I can’t believe it has only been a year since Aaron and I had that conversation. I think it was December 28th, 2014. The network did not exist back then. The network started this year. Lambo Goal started this year. In the Boat With Ben, the Podcast Dude, and Invisible Details, all of that was just this year. We’ve done a lot!
  • 07:47 Ben: It accelerated so fast. I can see how that kind of got away from you, Sean. You know what I mean. You’re meeting with unsolicited advice, and it wasn’t like the amount of content you were putting out was unhealthy necessarily, but you kind of scaled with the growth happening in your company and almost all of a sudden found yourself needing to do something about this. Sean, you’ve been extremely agile with all of this stuff. It’s cool to watch it from the outside and the inside, too.

The Hustle

  • 08:47 Sean: I’m able to produce so much because I get my back up against the wall and I make commitments. This year, I’ve found the upper limits of that. I’ve made the commitments, so I do three live shows a week. I’m doing a seven day a week video show on top of everything else. Because I made those commitments, I hired to help us be able to sustain that. I did that without regard for whether that was the best short term move to make. I wasn’t thinking about short term at all. I know that all of this will pay off in the long term, but I did know how much investment it would take upfront so that we would really have to scramble. We’re at capacity as far as work, but we still needed to do payroll, which meant me working even more. It got kind of crazy.
  • 09:55 Ben: It is crazy. I don’t know how you do it, Sean.
  • 10:01 Sean: We’re doing okay. I think we’re going to be fine. It just took more hustle than I wanted to this year. I did the calculations, and even with sabbaticals off, I worked 5,600 hours this year. A normal 40 hour a week job is 2,000 hours a year. That’s just nuts. That’s not what I want for the next year.
  • 10:37 Ben: It’s not just about not overworking yourself, but it’s about finding that sweet spot for where you’re working enough to pay your bills and grow but you’re not working so much that you’re going to eventually burn out. If you’re a person who’s pushing, who’s trying to get into that, it becomes this wave form.
  • 11:22 There are so many other variables and stuff like that. You can’t help but oscillate and jump around that sweet spot, sometimes dipping outside of it. In my position, where I don’t have nearly as many moving parts on the work side of things, it’s still a struggle for me to keep that in mind and keep that balanced. When you have more complexity, like employees, various expressions of your brand like the business, the lettering, and the store, maintaining them and knowing when to hire and when not to hire feels overwhelming to me. If I was in your position, Sean, I wouldn’t be able to do anything, because I would spend all my time and energy thinking about how I’m going to keep all of this stuff in balance.
  • 12:29 Sean: That’s kind of where I am. It is a lot of hard work. I don’t do anything but work, that’s my life, and I really enjoy it. It’s not so much that that I’m worried about. I’m figuring out how to sustain it, and we do that. I’m fine with all that. My concern is not about how to sustain this and how hard this is. That’s status quo for me now, but it’s more about opportunity cost. If all of my efforts are in sustaining what we have, I’m not able to take a step back and say, “What could I be doing if I wasn’t doing all of this?” I’ve taken it for granted that, because I’ve made commitments, this is what I should be doing. If I think about the next five years or so, where do I want to be and how do I get there?

Is what I’m doing today on a day to day basis the thing that will get me to where I want to be?

  • 13:39 I think the answer to that is, “Yes.” I think that what we’re doing now is what’s going to get us to where we want to be, but I think this all culminates in more short term thinking. I take for granted the long term so much that I worry that maybe I won’t have that long term. What if I die in a year and I’ve written no books? That kind of sucks. Maybe that’s just a personal goal.
  • 14:23 Ben: Somebody could compile all of your content and put it in a book.
  • 14:26 Sean: They could. That’s essentially what I’d be doing, so maybe it’s not that big of a deal. Maybe it’s just an issue of personal accomplishment.

Attitude Toward Goals

  • 14:49 Ben: I wonder how many things are this way for us. Like you said, Sean, one of your goals is to write a book. One of Rachel’s goals is to get a book published through a traditional publisher. One of my goals used to be playing in an amphitheater to tens of thousands of people. There’s the idea that we have in our heads, and I try to deconstruct that. I take that idea apart and I think, “Why do I have that as a goal? What need or desire does that fulfill for me?” Playing to a full amphitheater involves significance. It’s exhilarating, there’s a rush there. The significance is that I’m sharing something I love with people who love it. There’s this mutual thing going on, where I’m sharing something that started out as something really personal for me. I’m giving a piece of myself away, and people are excited that that’s happening, they’re receiving it, and they’re reciprocating it.
  • 16:36 Through the cheers and the clapping and all of that stuff, there’s that experience. There’s also the awe of having that experience. I find all of these pieces and I’m left with a question without an answer. Maybe it sounds like I’m giving up, but my question is, “Do I have to reach this idea of what I have in my head in order to be able to have these experiences?”
  • 17:18 Sean: When I’m thinking about my goals, I’m pretty happy with my life and what I’ve accomplished so far. If I did die in a year, someone could compile what I’ve put out so far into, hopefully, a number of books. If they studied the material enough, half the work is already done for you with shownotes. I would like to be able to have a hand in that to craft the narrative I want to be able to tell, but it’s not the end of the world if I don’t write a book. That may be a goal for me, but it’s okay if I don’t accomplish it.
  • 17:59 I’ve spoken in front of people, I’ve helped people, I’ve grown a large audience, I’ve been able to sustain myself and help and inspire other people. I think the only thing I still have on my bucket list is that I want to write a stand up routine and do that. I want to travel more—we have places we want to go. I want to get to what you’re saying, Ben. I really have reached most of my goals, except my one big goal, which is the Lambo Goal. The Lambo Goal isn’t about getting a Lamborghini, it’s about accomplishing my big goal and proving that I can do it. I’ve proved to myself that I can accomplish lesser versions of my goal.
  • 18:52 I remember this one speaker, some motivational guy, and he was talking about how, when you envision your goal, this big thing that you want to accomplish, and you take the elements of it, there will always be a lesser version of that goal. Why do I want a Lamborghini, specifically? As a kid, maybe I had my reasons, and maybe I convinced myself that I just wanted a kind of cool red car. I settled for a Mustang, and I worked in high school saved up the money, and bought that car. I accomplished that goal. I set very specific criteria for it, and I accomplished that.
  • 19:43 It was a lesser version of my ultimate goal. If I say, “Why do I want a Lamborghini?” Well, I like that it’s red. I like that it goes fast. I like that you can hear the engine. You can take all of those things and say, “You could buy a Corvette or a Mustang.”

There are always going to be lesser versions of your goal that you could settle for, but I don’t ever want to settle.

  • 20:22 Ben: I struggle with that a little bit, not because I disagree. I don’t know. Maybe I’m more willing to settle than you are, Sean, and that’s something I’m dealing with. I’ll jump off of that real quick. I had this thought earlier this morning about our attitude toward our work and our attitude toward working toward our goals. It’s the difference between satisfaction, being satisfied, and being content. When I think of the word “satisfied,” that feels like an ending to me. Satisfying a debt is paying it off, and that debt goes away. Contentment doesn’t take away the dissatisfaction that drives us toward whatever the goal is, but it also allows us to be content. If things never change, if they always stay the way they are, I feel content. There are two conflicting things. We can feel content but also feel dissatisfied.
  • 22:09 Sean: It’s weird with all of the definitions and stuff, but I can relate to what you’re saying. I am happy now, and I understand that, at a fundamental level, you will only ever be as happy as you are now, in this moment. All you ever have is now, and if you can’t learn to be happy now, you only learn to be dissatisfied with your current situation and think that the grass is greener. There’s a reason people say that cliche. Once you get out of this job that you hate, if all you’re focused on is how much you hate this job, you’ll get an attitude where all you focus on is what you hate in the next job. You can only find fulfillment in where you are now. I’m incredibly happy and content.
  • 23:00 Ben: Maybe it’s about fulfillment vs. satisfaction.
  • 23:04 Sean: I was working towards fulfillment. I like the word “fulfilled,” because I’m fulfilled in the chase, in the climb, getting to the place I want to be. If I don’t make it there, that’s fine, because I like the thrill and the enjoyment of the pursuit and the effort. I am fulfilled in that, but I don’t want to settle. I’ve settled before in life, and it showed me that I can accomplish what I set out to accomplish. Why should I set out to accomplish small things? Why does Rachel want to be a published author? It looks legitimate and if you’re published, you have distribution. If you can be distributed, then you have more reach. If you have more reach, you can impact people. If you can impact people, you can change their lives. You can say, “There are ways to have influence, distribution, impact people, reach, and help people’s lives without being published,” but that’s her goal. That’s her goal, and anything less would be settling.

As long as you find fulfillment in the now, in the pursuit, don’t settle for anything smaller than your goals.

  • 24:18 Ben: I don’t know if she’s listening or not, but I absolutely, 100% believe in her and her ability to reach that goal. I have no doubt that she’s going to do it. When I used that as an example, that wasn’t to say that she should deconstruct that. Now I’m questioning myself and that dream I had of playing to a packed out amphitheater.
  • 24:44 Sean: You will not accomplish that if you lower the expectations for yourself. If you keep those expectations, I think that you will accomplish them.
  • 25:02 Ben: What do you stand to lose either way? If the journey toward that goal is fulfilling, then whether you ever realize that goal or not, you have the most valuable part of it, which is the journey to get there. There’s nothing to lose. I guess you could stand to lose in that somebody could say, “You’re foolish for wanting that, because only a handful of people ever get to have that experience.”
  • 25:48 Sean: That’s because most people listen to the person who’s saying that stuff. Maybe, for a moment, I was concerned that the aspects of the journey were not actually what I wanted to do. I don’t even know that. There’s just the possibility that that could be true, and I don’t know because I haven’t taken a big enough step back. I want to make sure I’m staying vigilant enough to where I’m not locking myself into a commitment. Going back to what we were talking about in the last episode about setting expectations, maybe you set the wrong expectations and you have to reset them, and not just say, “I want to stay true to my word and my commitment, so I’m going to keep going.”
  • 26:49 At some point, maybe we do need to reevaluate. Maybe it’s not all about my ultimate goal. I am happy and fulfilled in what I’m doing. If I did die and I hadn’t written books, that would stink. I started thinking about whether there’s a way to carve out a bigger section of time that could be focused to just accomplishing big things along the journey. It’s a big, tangled thing, but a good conversation.
  • 27:26 Ben: If you zoom out far enough and you run it through the filter of your values, you look at your goal and where you are now, there are potentially still several different paths. You’re on one right now, one of many different possibilities.
  • 27:49 Sean: I saw someone who wrote an article mentioning me, and in telling my story, they said that I was a designer and did all these different things, but it was when I decided to specialize and only do handlettering that I experienced success. Isn’t that a scary thing, only choosing one thing for now with all the paths you could be choosing?
  • 28:17 Ben: You can’t walk on more than one path at once.