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Imagine the Possibilities: How to Break Ties That Hinder Our Potential

Episode 10

Often times people find themselves in a place where they feel trapped or stagnant in their lives. It can be trapped in a job or in a relationship and making a change may not always be the easiest thing to do. Because we are human, we find ourselves in situations where it is hard to leave or change because we are connected to people, systems or organizations. 

In this episode of Programming Leadership, Jessica Kerr joins me to talk about the complex topic of moving out of stagnation and into new possibilities.  We also cover some mechanisms for people to implement who want to make a change in their lives when it seems almost impossible to do so. 



Show Notes

  • People are connected in many systems and because of those bonds it’s hard to break them and make changes. 
  • In order to make a change you first have to imagine yourself doing something different or get others to help you make those changes.
  • If you are feeling trapped in your work, conduct some what-if scenarios but don’t impulsively act on those scenarios without first examining how you feel about them.
  • Don’t picture going somewhere new when you are doing what-if scenarios, better yet picture arriving at your new destination. 
  • Take little steps that can open up new opportunities like blogging or joining a new organization. 
  • It’s okay to want something new for yourself.



Announcer:  Welcome to the Programming Leadership Podcast, where we help great coders become skilled leaders, and build happy, high performing software teams.


Marcus:  Welcome to the next episode of the Programming Leadership Podcast. I am Marcus Blankenship and I am just super excited to have my friend Jessica Kerr with me today. We are going to have an interesting conversation live without a net about all kinds of brilliant topics that I know you’re going to enjoy. And I suspect at the end, I might insert something that actually says what we talked about, but to me, that’s half the fun. Welcome, Jessica.


Jessica:  Good morning, Marcus. It’s good to talk to you again.


Marcus:  It’s good to talk to you too.


Marcus:  Well we got chatting over email, and I think there were a lot of things we were touching on, including perceptions and systems. In particular, I had sent out an email about if you had a magic wand, what would you change? And you replied back, as did thankfully a lot of other people. I noticed that a lot of the things that people replied to were things that from the outside, from my completely unbiased, uninformed opinion, I thought, “Well there must be something they can do there.” But I think a lot of people also wrote me back and said that they felt pretty trapped, that they weren’t sure what they could do. Have you ever seen or talked to people who feel trapped in their system?


Jessica:  Yeah, yeah. People often feel trapped or they feel helpless. Um sometimes there are obvious reasons, like they need the money from this job and they can’t just get another one. We accept those, but I think I think there’s a lot more to it than that.


Jessica:  When we’re part of a system, whether it’s a relationship, or a family, or a team, or a company, we feel those ties. And those ties are part of us. Humans, we’re not human independently. In part of the essence of humanity is that we form higher level systems with each other and those systems define us. And so leaving one of those, it involves breaking the self that exists. You’re breaking ties that are part of your daily living. We don’t know how to be, without being part of the family, and the company and the relationships that we’re in. And to change that is to find a new version of ourselves and that’s scary.


Marcus:  I knew we were going to get philosophical. Thank you for getting us there so quickly.


Jessica:  Well we got there really fast.


Marcus:  We did. And and you had sent me a tweet and I saw a bunch of other people were loving it, that was just really recently, but it was about that same idea of when you’re leaving, it feels really painful, when you leave a company, when you leave a system. There is some feelings associated with that. Where did that tweet come from for you?


Jessica:  Ooh, um that’s a good question. I was thinking about how we’re not we’re not human as individuals. The functioning unit of people is not the individual person.


Jessica:  Well one thing I find really interesting about humans is that we’re part of many systems at once. We’re part of a nation, we’re part of the global humanity, and then we’re part of our town, we’re part of our company, we’re part of our kids’ soccer team, and our church and all the different organizations we join. We’re a part of all these simultaneously, but our work is a big one and it’s scary to change that. And and all these people around us, they have expectations of us. To defy those is hard. Sometimes I have to remind myself that the hardest expectations to defy are my own.


Marcus:  Ooh. That makes me think that we’re in a system with ourselves. Not alone with ourselves, but I noticed that for myself, I have a thought life that’s explicit, like I am trying to think about something smart to say next so that I can keep up with you. And then but I also have inner reactions that don’t appear to be as intentional. So I feel like there is an inner system at play for me as well. Maybe that’s just me.


Jessica:  Oh no. No, no. There’s present self and our future selves that we’re like negotiating with, or our many possible future selves.


Marcus:  And of course our past selves. I think they call that baggage that I tend to carry around and present to everyone I meet immediately. Oh, don’t mind me lugging around seven suitcases full of past baggage about all the things that I perceive define me and define you.


Jessica:  Oh, the other day I listened to an Amanda Palmer song. Oh, it was heavy. Amanda Palmer over breakfast is dangerous. But it was relevant to this. It was about why am I not the person I wanted to be. And and at the end of the song she’s like, “No, I am the person I want to be, dammit.”


Jessica:  But I’m kind of like, “Well why would I not want to have that pull? I always want to be a little different, I always want to know more things, I want to meet more people.” I mean I’m good with who I am now, I’m not picky, but it’s good to want to be something more.


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Marcus:  Yeah, I think that there’s like a tension for me. There’s learning to be okay with like I just turned 49, which is my kids have called very old, halfway to dead, other things like that, right very jokingly. But at 49, I’m pretty okay with parts of me, but I’m less okay with other parts of me because I see possibilities for developing those parts. And I think that’s what scares me about if you’re half done with the race, what are you going to do with the next half? But there is a real truth to learning to be okay with yourself and yet also keeping attention that says, “There are more possibilities for me to grow and change.”


Jessica:  Oh yeah, I’m good today but I don’t want to be the same tomorrow. You used an important phrase there. You said you could see possibilities for yourself. And that is another big thing that keeps people in situations where they’re not happy and they’re not growing, is because they either can’t picture themselves someplace better because they’ve never seen it, or they can’t picture a path from here to there that they find acceptable.


Marcus:  Boy you okay, so you nailed it. The email you replied to me on was just something really vague. If you had a magic wand, what would you change? What’s your wish?


Marcus:  This morning I emailed out what’s the obstacle. And you might not be surprised to hear that only about 5% of the people who emailed me with wishes responded with what’s the obstacle, because I think that’s such a harder question. To even know what’s in your way requires picking a perspective, thinking about it like on a map and saying, “That’s the mountain I have to climb.” I don’t even think it’s that the mountain is that high, it’s that often times we’re not oriented. We we’re lost. We know we want this outcome, but do we head north, or south, or east or west? And that’s why I think that question of, “What’s in your way?” was unfair and really hard to answer, which is why I think people didn’t.


Marcus:  I did a little self-analysis this morning. I chose something that I wished and that was easy. And then I thought, “Oh, what’s standing in my way?”


Jessica:  Well now you have to get concrete. What did you choose, Marcus?


Marcus:  Oh, oh. I was not expecting you to ask that. All right, I should have been, but I wasn’t. I chose, this is going to sound so whiny. Is that okay? Could I whine on …


Jessica:  Yes.


Marcus:  Okay. I chose to have something I deemed as a business that was steady.


Jessica:  That sounds like an oxymoron to me, sorry.


Marcus:  A business that brought in income regularly.


Jessica:  Okay.


Marcus:  That is, I would know what business I was in, and I would be able to see the value I add, and I would be able to understand what levers to pull, what effort to exert. This has been something I’ve struggled with for a number of years. People will say, “What do you do?” I’m like, “Uh, I don’t know but … “


Jessica:  That’s a Patreon’s question, what are you creating?


Marcus:  Right. Every time I’ve gone to Patreon and I thought, “Well, I’ll sign up.” I’m like, “I guess this isn’t the place for me.”


Marcus:  So that existential angst of asking the question, “What do you want?” So okay, I don’t even care if it’s doesn’t have to make an amount of money. I don’t want fame and fortune, but I thought, “I want a little business that just toots along, and is reliable, and I can count on, and is something I call steady.” But then the question of, “What’s the obstacle?” was like naval gazing for 45 minutes.


Jessica:  Oh yeah, because it’s not what’s in your way, it’s what do you even want to do. You’re looking for an abstraction there. A steady business is not a thing. Business is not a thing. Okay it’s like you study business, what does that even mean? You have to have a business. General business skills are only valuable when they overlap with specific concrete know how.


Marcus:  Absolutely.


Jessica:  Yeah, so you just don’t have a concrete picture.


Marcus:  And so the wit. Right, that’s right. I have an abstract picture. And some of the people mainly, I’m looking at the list right now, I’m gonna…


Jessica:  That’s the kind of wish a genie could really screw you over on.


Marcus:  Yes. I will bet that many of you listening say, “You’re an idiot, Marcus. I have steady income and I hate this place. So be careful what you wish for.”


Marcus:  For people who are listening who say, “But Jessica, I really do feel trapped at this company? Like I’m not going to move up, I’ve got skills to do this job, I performed some career limiting move or my boss hates me. I live in the middle of nowhere, Oregon. This is I really feel completely trapped”? How can people begin to see new possibilities? You threw out one way and that was ask others. Is that right?


Jessica:  Yeah, yeah. But even for that, so you have to have an idea.


Jessica:  My concrete suggestion is to do some what-ifs. And make sure you have no expectation of yourself actually doing this, because that will free you to go wild the what-ifs. What if I moved?


Marcus:  Uh, that’s scary.


Jessica:  Right, it is scary. But what if I did? What if I lived somewhere else? Then picture moving your family or leaving your family if it’s not healthy family, or traveling all the time. You know what, if picturing that really sucks, great. That has its own uses of making you feel better about the things that are happening in your life. And then picture ways that it might be really interesting or good things that could come out of it. And then don’t picture quitting. That’s not the goal.


Marcus:  Picture quitting.


Jessica:  No, no. Picture where you are next after you quit.


Marcus:  Now tell me about that, because I feel like if I were to … Let’s say I worked at a job and I was doing what you suggested, and that was picturing picking up my family and moving to a new city, quitting would probably be a part of that.


Jessica:  Yeah, that’s fine.


Marcus:  But you say avoid picturing the quitting event.


Jessica:  Don’t think about what you’re leaving, don’t think about the leaving process, think about the going to.


Marcus:  It’s not about running from, it’s about running toward?


Jessica:  Right. Right, right. I mean if your company went out of business tomorrow, what might you think about doing? Just take something where you live now, your town disappeared, you don’t live there anymore. Where do you live? So yeah, don’t picture the going because that’s not going to help, picture the arriving and the being in some completely different place.


Marcus:  I think I’m a lot like some people, maybe everyone, I don’t know, that I definitely experience a fear of loss.


Jessica:  Oh yeah.


Marcus:  And when I think about leaving, for example, this morning I thought, “Well maybe I should just pack this business up and sell beach towels on the internet.” That’s a whole other kind of thing, and I’d just pack it away. The thought of leaving it, was I had a visceral reaction to it.


Marcus:  But the thought of doing something new and different that met my goals of whatever I was wishing for, that part was really exciting. And I don’t think this is going to turn into a beach towel podcast, but I’d like to reserve the right that could happen.


Jessica:  Well make sure you sell beach towels in both hemispheres because otherwise it’s not going to be a steady business.


Marcus:  See, that’s the kind of wisdom you get from talking to somebody else. Great point.


Marcus:  Okay, so avoid that, the idea that well I just have to escape here.


Jessica:  Yeah.


Marcus:  And think about where it is that … Think about just … This sounds like a fantasy, these what-if fantasies you allow yourself to have.


Jessica:  Yeah yeah. And they don’t need to be what if I got a million dollars. It’s not some external thing. It’s what if I couldn’t do what I’m doing now, what would I do then?


Jessica:  Another thing that you can do to reduce the feeling of being trapped and open more possibilities for the future is generally things that open more possibilities, including learning and then blogging. Blogging on the internet is huge because when you do need a new job, you can point to a blog. That makes a big difference. People can see how you think.


Jessica:  Or find someone who is doing something that you wish you could do, and yeah, ask them how they got there. Or just picture yourself doing that. And speaking at conferences if that’s your thing, well whatever, it opened all the possibilities for me. But just kind of getting out of your bubble just a little bit, once a year, and meeting people who are doing things other than what you’re doing.


Marcus:  I’d like to dive into this conference thing, because as somebody who is a hermit, going to conferences are not terribly comfortable for me.


Jessica:  Even better. Well.


Marcus:  But you describe them as really impactful, I think. It’s not quite what you said, but they opened up a lot for you. I think in your email, the way you phrased it to me was it sounds like you feel almost a calling or you feel something about going to conferences. Is that right? It’s not just a mechanism to get what you want, it’s about something else?


Jessica:  Oh. Well I when I speak at conferences, and people come up afterward and they say, “Thank you for that talk. It gave me a new way to think about my work,” ahh then I feel nice. I feel a sense of meaning and purpose. I’m having an impact on the wider system that is this whole software industry. That feels really good, and that feels like I should keep doing it.


Marcus:  I’m glad you do it. I watch them on YouTube sometimes. As a hermit, I see them out there. It does go back right, to what you said at the beginning, we are all part of the system called humanity, and earthlings, and the universe.


Marcus:  I also have this idea, and I want to be careful here but because I might be wrong, but I have this idea that often times we live in these self-imposed cages where we do the things we think we’re supposed to do. And we see boundaries because people have nudged us if we are out of bounds or we say, “Well, we couldn’t do that here.” There’s no written policy against it, but its … Like I was talking to somebody the other day.


Jessica:  It’s just not done.


Marcus:  Yeah, and they said, “Well managers always eat at their desk. I said, “Well could you go eat with your team?” This person was lamenting they didn’t get more face time with their team. They said, “Oh, that’s not really the way things are done here.”


Jessica:  Yeah, and as I think you said in that email, “Then expect the same results.”


Marcus:  Well that’s a good way to put it, yeah. But I just I think to myself, “How many things at big companies I’ve worked at did I not do because I perceived the need to fit in and the need to do what was done there? And I wish I had eaten away from my desk more, but I think you have something to say.


Jessica:  Yeah, yeah. There’s something that’s come up a couple times and it comes up here. There’s not a barrier to eating away from your desk. It’s not a physical barrier. You are not forced to eat at your desk, but you are inclined to eat at your desk because that’s what you observe around us and we are not independent beings. We are strongly influenced by what we see around us, and that’s what seems normal and right to us to do.


Jessica:  But these are all inclinations. They are all percentages. We don’t act out of a specific decision of well, our will and our intention influences what we do, but it doesn’t force what we do in a Newtonian physical sense because our actions are a thousand million decisions that we do not think individually about. I am not thinking right now about twiddling with my pen, I’m just doing it. And those inclinations are strong.


Jessica:  We talked earlier about what obstacles are in your way. Often, you can’t name an obstacle that’s physically stopping you from doing something. Think instead, instead of asking yourself, what is the obstacle, and you also ask yourself if there are obstacles because you have to think about those, but what is inclining me to keep doing it this way? What inclines me to not work out in the morning like I intend? Maybe it’s my sleep hours end at seven, and that’s when my body wants to get up, and that’s too late to work out, and workout at noon. Noon, you’re more inclined to work out and so you will. Don’t act like we’re these balls of will that control everything we do. Oh, that’s so effortful and have other things we could turn our brain to.


Jessica:  Avdi Grimm yesterday said something about we’re marbles on an uneven surface. And we can roll up hill a little bit if we try really hard, but our power as humans is really in changing the surface, in changing our situation. You could do that sometimes in subtle ways, by talking to those customers differently so that their situation is a little changed and they’re more inclined to be a wave that has the same purpose as patience with you. Maybe choose to eat lunch that is not practical to eat at your desk. Bring something really messy.


Marcus:  A taco bar.


Jessica:  Yes, yes. Bring tacos that you can’t eat in front of your computer, and so you have an excuse to eat in the cafeteria with your team. So we yeah, yeah. But don’t just look for obstacles, look for changes in your inclination.


Marcus:  I love the word inclination. Of course, I think the root is incline, which sounds a lot like going uphill, which sounds a lot like putting a lot of effort into it. And yet when I am inclined to do something, I feel as though as if I am slipping downhill into it.


Marcus:  Whether you consider it going up or going down, I think about a diagonal line as an incline. Maybe I shouldn’t, but that’s what comes to mind is an incline and I love that you’ve put that phrase, it becomes the tendency, my default, the thing that I don’t even think about.


Jessica:  Right, but if you can set up your situation, such that the thing you want to have done is also the thing you’re inclined to do.


Marcus:  Right, and I was just thinking about this exact … Oh, it’s so funny because I was trying to figure out, what if there is, I called it a river of energy, a river of intention, things that I enjoy, and by river I mean there’s a current to it, which also like an inclining has a motion aspects, why aren’t I looking and doing those things that I find effortless? Maybe other people find them very difficult, but I find effortless and joyful. Those seem like the things …


Jessica:  Like this podcast.


Marcus:  Like this podcast. Easy as pie. I said, “You want to do it?” You said, “Sure.” We’re having this nice conversation. It doesn’t mean that the Marcus was born into the world doing this, but it does mean that he learned to get to where this is comfortable.


Marcus:  Now I’ll be honest, and I don’t want you to take this the wrong way, if you were Bill Gates, I would have been much more nervous today. But because we had chatted before, and had a very informal email exchange, and I’ve watched a lot of Bill Gates videos too, but I would have felt completely unprepared for that.


Marcus:  So I have, at least this point, I would say I have learned to interview Jessica. That is an accomplishment for me, but it was learned. I didn’t … Don’t anybody who’s listening think that Marcus is a natural at this.


Jessica:  Yeah, that’s important. All the people that you admire. Bill Gates wasn’t always a CEO and everything else he is now. We all learned what we’re doing. Some of us are still uncomfortable at it and you don’t see it.


Marcus:  Oh, I’m always comparing my inside to your outside. That’s my default state, is assuming that you’re put together and I’m not.


Jessica:  Yeah. One thing I learned really early when I first started speaking at conferences were that all the other speakers were just people, and especially at software conferences. People in general are not speaking there for some like self-importance. They’re speaking there because they have ideas, and they want to share their ideas, and they want to hear your ideas, and they want to combine more ideas. It’s just you know people.


Marcus:  So let’s recap here. If somebody is listening to this and it’d be nice if someone did, so if you’re out there and you’re feeling trapped in a system, and you think to yourselves, “I would like to see new possibilities,” one way to do that is through giving yourself the permission to use what-if scenarios, knowing you’re not going to impulsively jump at any of them, but gaging your own reaction to the way it would feel for you to show up for work at a new job, for you to pull into a new town with your family, for you to … I don’t know what it would be. But if you’re envisioning it …


Jessica:  For you to get up and work every day for a couple hours at your steady business.


Marcus:  Exactly.


Jessica:  Okay so that was one action item, was imagine yourself in a new place and is that stimulating to you or is it not? So there you can find things you may want to change.


Jessica:  Another is just take little steps that open up opportunities like learning new things, blogging is really good, join new communities.


Marcus:  All of these are about connecting with people that you weren’t connected with before or in different ways.


Jessica:  If you feel uncomfortable about talking to someone, then just try it. It’s not going to be as bad as you think. Worst-case, they don’t talk back to you.


Marcus:  Right. That happens all the time.


Marcus:  I was at I think there’s a theme here. I was at Problem Solving Leadership about a month and a half ago, and this wonderful gal from Sweden used this phrase that I wrote down, and she said, “Remember, you don’t have to choose from the options before you.” I like that because the concept of the options before you are the things I can see right now that seem like the only choices I have.


Jessica:  Yeah, yeah. A promotion is not the only career progression.


Marcus:  Also not the best.


Jessica:  It’s the one in front of you, it’s the default, it’s the one everybody’s competing for, so go find something else that other people haven’t seen.


Marcus:  And I think be honest with yourself. Let yourself say what you want, what you wish for. A lot of people don’t feel like they’re allowed. And I wonder how many people emailed me with something they wished for that they’ve never verbalized, that they’ve never told their spouse, they’ve never told their boss or their client. And I wonder. Here I’m looking at this long list.


Jessica:  If you don’t ask, you can’t complain.


Marcus:  Funny, they’d still do. It’s funny, I still do. Giving yourself permission to want something, I think is an important step. A lot of us learned, maybe as small children, that wanting things is selfish, and selfish is bad.


Jessica:  But wanting things is essential. This gets back to seeing new possibilities, to the new version of yourself, who do you want to be. I think one of the saddest states that humans can get in is not wanting anything.


Marcus:  I would agree with you. My wife was a hospice nurse, and even those in the last moments of life, you’re probably aware of this but when there’s a pattern. When someone is been sick a long time, they’re on hospice and they’re going to die, if there is something unresolved in their life, they will hang on and suffer. This is particularly true if they’re waiting for family to come in. Hospice nurses, this is real, they do this thing where they have been trained to simply tell the patient, “It’s okay to go, we’ll be okay. The people here will be okay.”


Jessica:  Nice.


Marcus:  And literally, my wife did this so many times when she saw that people were hanging on and really suffering. And she would just have a quick talk with the person. I hate to say it, but it would be an hour and they would slip.


Jessica:  Nice. So you can do that for yourself at your work. It’s okay to go. The people around you, they’ll be okay.


Marcus:  They’ll be okay. Your project, it’ll survive.


Jessica:  Yeah, yeah. Or it’ll …


Marcus:  Or whatever.


Jessica:  It wasn’t going to go into production anyway and it can just be fine.


Marcus:  Whatever it is. Those around you, you don’t have to hold it all together.


Jessica:  No, you don’t. And without you, the company will be a slightly different system, and it will be okay. And whatever new place you go will be better for having you.


Marcus:  Part of humanity is the circle of life, and we could get all Lion King and everything, but the reality is, is we come in and then we leave. That’s a part of it.


Jessica:  In employment it happens faster.


Marcus:  It happens fast. That is a true statement. No one is employed at birth. Well, that feels like it gets into another topic we don’t need to talk about.


Marcus:  Jessica, thank you so much.


Jessica:  Thank you, Marcus.


Marcus:  Where can people find you online?


Jessica:  Well you can find me on Twitter @Jessitron. Also,, J-E-S-S-I-T-R-O-N. for the newsletter. Oh, on Twitch it’s just Jessitronica.


Marcus:  Are you speaking this year at any conferences we might go find you at?


Jessica:  Sure, sure. I’m keynoting RubyConf this November, I think in Nashville. I’ll be at UberConf in Denver in July. Oh, where else am I going to be? Southeast Ruby, also in Nashville. There’s a couple others. You can check my website. It might be up to date. Thank you, Marcus.


Marcus:  Thank you.


Announcer:  Thank you for listening to Programming Leadership. You can keep up with the latest on the podcast at, and on iTunes, Spotify, Google Play or wherever fine podcasts are distributed. Thanks again for listening and we’ll see you next time.


Announcer:  This has been a HumblePod Production. Stay humble.



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