Building an Intentional Career and Organization with Barrett Brooks

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Barrett Brooks believes that business, when done right, can be one of the most powerful forces for good in the world.

His career took a sharp turn when the path he planned ended up feeling empty. This sent him on a journey toward discovering what makes meaningful work. I’ll let him tell his story.

But needless to say, Barett has thought long and hard about work and meaning, both for himself as well as for his organization. Today he’s the COO of Convertkit.

Self described as a Husband. Father. Change maker. Optimist. and Environmentalist, I loved connecting with Barrett and hearing the many twists and turns it takes to find your way in your work. I left this conversation feeling so grateful for the intentionality he brings to the organization that he’s building, and hope to do the same in my leadership.

Listen in here:

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In this episode you’ll learn:

  • What Barrett is excited about right now
  • Where his journey toward meaningful work began for him
  • What he’s learned along the way 
  • How he thinks about the impact that he is trying to make
  • When to decide to stay in the course or move on from a job/project/idea
  • How he determines culture and environmental fit in the hiring process
  • How Convertkit uses an exercise called “Listening walks”
  • What are the eight things that contribute to meaningful work

Resources Mentioned:

Barrett’s blog

Barrett’s LinkedIn


Reboot by Jerry Colona



Barrett, thank you so much for joining me. Barrett, thank you so much for joining me. Welcome to the Meaning Movement podcast. So, so happy to have you here with me.


Yeah. Thanks so much for having me. Dan, I’m excited to be here.


So question I’d like to begin with is, how do you begin to talk about what you do in the world?


Yeah, it’s always one of those questions, you know, that sometimes has that knee jerk response. But I was talking to a friend recently about the degree to which it’s kind of gotten a little old and tired for people to even respond to, because everywhere we go, that’s what people want to know. What do you do? What do you do?

And one of the questions I’ve started asking instead is, what are you excited about right now?


I like that.


And, what I found by asking that is you really get a truer sense of who people are.

And it highlights to me that often who people are is not aligned with what they do. But for me, that’s very much not the case. I very much enjoy my work. I am the COO at Convertkit. That’s a fancy way of saying that, I do a little bit of everything. I’m kind of like the, one of the generalists on the team at Convertkit. We make e-mail marketing software. Really it’s software that helps you build an audience as an independent creator and service of our mission to help creators earn a living.

And when we think about creators, we kind of define that as anyone who makes original work to teach, inspire or entertain an audience of dedicated fans.

So this work is kind of what I’ve been building towards, I think, my whole career. And I’d say the through-line of my career from beginning to end has been this question. The central question that I think you are also asking and answering on this podcast, which is what makes work meaningful. And so that’s kind of how I think about my job, is how do I create an organization? How do I help create an organization where our team can find their work meaningful and where we can really be in service of our customers day in and day out?


I love it. And for anyone listening who is on my email list, you’ve received e-mails via Convertkit from me. If you’re not on my email list, you should go to the meeting movement and join in. But I’ve been a longtime Convertkit user and just big fan of what you’re building. As you know, from the user standpoint, I love it. It’s fantastic. And it also seems like just a really cool company. Lots of good things that you’re doing.


Thank you for that.


And a part of which, and I’m sure we’ll get into some more down the road. But let’s just kind of rewind a little bit.

How did you get here? Where did this journey begin for you?


Yeah, when I get asked that question, I think I have to go all the way back to about the midpoint of my college career.

And the reason is that, that was where I really started to be shaped as a professional or my professional perspective started to be shaped. And it kind of opened up different paths I could go down. And the key driver for that was I got selected into this two-year leadership development program that was almost like a minor in leadership at the business school I went to. And in the first year, it was focused on personal leadership. And so the kind of capstone of that year was a personal leadership development plan, and that included things like a vision for your life and career.

We wrote our own eulogies. We defined our values like we did all of these exercises to really try and get at who we are as people. And then the second year, we studied leading organizations. So what does it look like to take what you personally believe about the world and apply that in an organizational setting?

And that training is still very much present in how I operate today. My other experiences at that time on campus. I like to say that I majored in finance and accounting. But my real education happened outside of the classroom with all of the student organizations that I was a part of in the leadership roles I held on campus.

And I opened up these two different paths. One was the very traditional business school prestige status kind of path towards management consulting, investment banking, accounting, something like that.

The other was entrepreneurship and potentially starting something of my own. And that was kind of the choice I was making as I graduated was do I have an idea I might be willing to go try and start on my own or do I chase the status game? And I don’t know that it was that explicit at the time. But looking back, it definitely that’s the choice I was making. And in those situations, I think just as humans, we’re wired to want status because status is what kept us alive, you know, back before we had civil society and everything else.

And I went to work as a management consultant at Ernst and Young, which is now called E Y. And it was on the premise of this recruiting tale that all of the firms told that consulting is one of the best professions you can be in because you get to travel widely, travel regularly. You get to work with some of the most prestigious and large companies in the country. You get to see many different business problems from many different angles.

And that was very attractive to me. It seemed like a great place to start my career.

What I found on the ground was, it wasn’t very exciting. Number one, I got placed on a client in town in Atlanta where I was at the time. I was on the ground floor in this dark office building and the kind of like, it seems like a computer control room almost.

And I was working in a practice that was kind of tangential to the one I had been hired into. It was more of like a, a risk prevention practice, whereas I was supposed to be in a financial performance improvement practice. And I’ll never forget, the day things started to change was I asked one of the partners, hey, do we have a policy for allowing teammates or people at the company to take time away to go volunteer without having to take vacation days?

And they ran it all the way up the pole to the head of the Americas. And finally, the head of the Americas got back to me and said, well, I’m not sure it seems like we should, but I don’t know what it is.

And that really spoke to me about who they said they were trying to be versus who they were in action. But I ended up taking a week off and I went to a camp called Camp Horizon, which is in Atlanta.

And their mission is to restore dignity and hope to children who have been abused or neglected and are in state custody. And at camp, the camp counselor ratio is one to one. So throughout the week, you get assigned to a camper and you spend the whole week with them. And it was a very meaningful experience for me. Volunteering is always shaped me but that in particular really revealed to me a new part of the world that I wasn’t as aware of before that.

And in a midweek staff meeting, the chair of the board came in and he said, our campers are napping at this point. So it’s just the counselors. He said, well, I have some news. We’ve asked our camp director to move on. She had just been hired that summer and he was letting us know she had been fired. And the reason was that she was alienating all of these longtime volunteers. She was not a good culture fit.

And his next comment was for the next person who leads this camp as we head from this year to next year, we want someone from inside the camp, Horizon family. So if you’d be interested in applying for that role, let me know either today or sometime before you go home this week.

And in that moment, the juxtaposition between what I was doing every day, which was essentially shifting through spreadsheets, looking for documents to support tax audits for a Fortune five company. And what I could be doing every day, as revealed by this open roll now, which would be working with children who need help, who need resources, who are lacking love and hope. And just like a general sense of well-being in their lives, that, that is what I could be doing every day, my brain kind of broke and I realized that I couldn’t possibly continue on the path that I was on. And then I had to go find something else to do with my life. So that’s a very long entrance to say.

That was kind of a jumping off point that I think is really put me on the path that I’m on now. A month later, I ended up quitting my job. I considered applying for that camp director role, but instead, I founded a company called Living for Monday, where I wanted to help students and young professionals develop a sense of self-awareness and then apply that to finding jobs. So it was kind of like the personal development side of defining who you are. And then the job search side of the practical tactical resumes, cover letters, interviewing all that kind of skill set.

Great passion behind the business. Really bad business idea because students have no money and they have not yet felt the pain of having a job that is not meaningful. So about two and a half years into what became a three-year project working on that, I got really lucky and got my name pulled out of a hat to go to work with an author named Seth Godin in New York on a summer internship.




So it was a couple of week-long internship in his office in Hastings on Hudson, New York. And there were 16 of us that were on that team. And that project was where I learned that, number one my business idea, although it was important to me, was probably a failure, not unlike the devastating way, just in the sense that it was time to probably move on from that. And number two, I learned what it was like to work for someone who I truly believed in and who believed in me.

It was a real example of leadership that I had not had up to that point in my career. So I came back and within four or five months of that, I had shut down living for Monday and that created kind of this blank space. It was OK. Now what? And from there, I ended up getting in touch with a couple of mentors and just said, I’m looking to move on from my business. One of those mentors happened to be hiring at a company called Fizzle, which was an online education platform teaching small, independent online business owners how to run those businesses.

I went to work there as director of customer success and then led growth as well after that. And then went from Fizzle to Convertkit. So that’s kind of the path that might be more than you were looking for there. But that’s how I ended up where I am.


I love it. It’s so, so fantastic. And I knew none of that story, but just some amazing intersections. And, you know, I love Seth Godin’s work. He’s one of the few bloggers that I read everything that he writes. I myself have applied for internships and not been accepted. But I applied to work with Seth at different times of the past. And one of our early interviews was with Corbett Bar at a Fizzle. So if anyone’s interested in learning more about Fizzle, go back to the archives up to that episode, which is very, very cool.

What an amazing journey towards finding alignment of who you are and what you do. And it’s I think that’s kind of what came up at that camp for you, kind of that misalignment that what you were doing then is not in alignment with who you are.

How do you think now about your work, about the impact that you’re trying to make? I guess it’s another way of asking the question, but that’s so hard to put words to. But how do you now think about the work that you’re doing and how you’re expressing yourself and your values and your identity in that work?


Well, part of the goal of living for Monday, that original business that I started was to, number one, prove to people or try and help them understand that work can be meaningful. I think in the world there is this lack of belief that work can matter.

And I think that’s built up over time and working with a bosses and organizations that just beat you down and beat you down until you feel like, OK, will work is there to make money. And I better find meaning elsewhere. And I think on some level that’s true. You should find meaning elsewhere as well. But I don’t think that means we should write work off. And, trying to help people find those jobs, I learned that the hardest part is finding the organizations where you can show up that way and expect that from them.

And so the way I see my work now is creating an organization where that is possible. You know, there’s this hope when you start a business like I did, that you can help thousands and thousands of people go to work and find meaning. But sometimes what I’ve found is the best thing you can do is actually be an example of what’s possible. And then people will use that to go implement that in their own lives. My approach now is let’s make convert kit the kind of workplace where the people here become better versions of themselves just because they came to work here.

And so that’s kind of the core of what I’m trying to do today. I want to make convert kit, an example of a company that other people, other founders, other hiring managers can take inspiration from and then apply that to their own context of that.

Many more people can find a sense of purpose and a sense of meaning and what they do every day.


I love it. I love it. I’m curious about just as you transitioned from, I guess maybe with that internship with Seth Godin and making that decision to end living for Monday.

And, you said you realized it was a failure, not like not a maybe a capital “F” failure way, but just maybe not sustainable or not what you initially thought it could be.

When do you decide that you’d stay at the course and push through? I guess just to use Seth Gooden’s terms, like to get through the dip, right? Versus just decide that this is not the right thing and to move on from it.

And I’m curious specifically in your experience there, how that decision was made and what that decision was like for you?


Yeah, well, there’s never a right answer for these things. I think it’s always contextual and it’s always personal. I think the best gauge anyone can have on whether they should keep going is do they want to keep going?

Do you feel a personal sense of commitment to continue doing what you’re doing? That’s the first thing. And the second thing is, is it financially viable for you to keep going? You know, in other words, what’s the cost going to be for you to keep going? And sometimes the costs are large.

It’s your family. It’s money, it’s stable living environment. It’s healthy food on the table, it’s any number of things that the costs can be. And so if you’re willing to foot the bill of the cost and you’re still excited to keep going, I think you should keep going. For me, the key learning point was that I had learned a lot of what I set out to learn through that project, and I felt that I could apply that learning in other contexts and still continue the core of the work, even if the business itself didn’t continue.

Yeah, and that felt very freeing to me. I realized that while the business failed because it was not profitable and could not keep running financially, I had not failed. I had actually succeeded. It was a huge success of a project for me because rather than doing something like going to get an MBA or a graduate degree, I spent three years trying to really build something, talking to real people and customers, trying to sell something. Building a framework and a curriculum for how to go about finding meaningful work in the job market, practically.

And that’s priceless. So I think for me, I realized I don’t need this project could continue for me to continue to grow. And I don’t need this to be the way I earn my living for me to feel successful. So I think it’s an OK time to move on from this.


It’s cool. I mean, it’s like it’s almost like the project did for you what you were trying to do for others and some way.




Kinda little bit better, but it’s right on. Very, very cool.

For people who are listening that are kind of in these spaces where they feel this misalignment. They know that what they’re doing isn’t an expression of who they are. I guess the first question I have to or maybe it’s an invitation is, what would you have to say to people who are in those kind of spaces right now listening to this? They’re like, “Yeah, I’m working that exact job that you were at, feeling the same feelings that is just hollow.”

What do you have to say to them?


So much, but I’ll try and keep it short. The first thing is your tendency is going to be to run away from that feeling as fast as possible, meaning make the feelings stop. At the end of the day, it’s a form of pain to be out of alignment with yourself. And our instinct, everything we’re wired to do is to make pain, stop. What a lot of people do in that situation is they run to anything else that will make the pain stop.

It’s the same thing we do when a romantic relationship ends. In many cases, that’s kind of this idea of a rebound relationship is you end up in a relationship that was not intentional. It just relieved the pain. Yeah, a lot of people end up in jobs or starting businesses that relieve the pain, but they create new pains at the same time. So before you go running away and try and stop the pain, I’d say sit in it and try and understand it.

Try and understand what it’s attached to. Where is the misalignment coming from? Why don’t you feel connected to your work? Why don’t you feel aligned with it? And that’s deep work that takes time and journaling and reflection and a whole bunch of things that are going to seem like they’re not productive. But what you’re really trying to get at is who are you as a person? I think many people don’t know who they are. They have not defined who they are and who they want to be.

And that looks like things like what’s your belief system? You know, what are the things you believe to be true about the world or that you want to be true about the world? If you look at the different areas, you view your life between family and financial well-being and physical well-being and work and adventure and all of these other things, what matters most to you? What are you prioritizing? So I’d say start with you and understanding who you are, because only from an understanding of who you are, truly, you only have to be honest with yourself, that’s all you can do. Then, can you only find, OK, now how do I go find work that aligns with some of that? And I think it’s telling, especially if you’ve got a couple of different career experiences where it hasn’t worked out. You can start to find trends and pattern match. Well, why didn’t that first one work out? OK, well, my boss was kind of a jerk. He was a misogynist. I didn’t like working for him.

So I went to work for a leader I believe in. And that shares a belief system with me. OK, well, in the next job, what didn’t work there? Well, it was I don’t know. A diamond mining company. And I don’t believe in the way that we were going about getting those precious stones from the areas we were getting them from because the labor practices or something like that.

OK, well, whatever the end product is, I have to be proud of at a minimum, the way we’ve gone about making it. And that’s why I think going back to tying into my story that early business didn’t work, because if you don’t have any career experiences, it’s really hard to triangulate what it is that you’re looking for. So that would be kind of where I’d start.


That’s great. That’s really, really, really great. So much this just resonates with so many of the questions that I often hear from listeners who have worked with one on one. Back when I was doing one on one coaching around these ideas. But often people enter the conversation wanting just that fast, fast solution to that pain point. But sometimes that’s necessary. Sometimes if you’re in a job that’s really damaging, I guess sometimes it’s good to just get a different job. Yes. But the first step of that process is if you’re paying the bills like that’s the first place you’ve got to start. You’ve got to have the bills paid to create the space for you to start doing some of this deeper, I think, deeper work that you’re inviting people to.

I think it’s important if you can stay at your job right now and it’s not the best job in the world, but it’s paying the bills and gives you kind of that baseline to build upon. That’s a good place to stay while you’re doing the other work of really seeking to understand who you are and what you want. Yeah, just great, great words of wisdom. an

I’m curious, as an organization, the work that you’re doing with Convertkit. How do you make an organization, a culture where these kinds of deeper questions are invited? I mean, I think there’s lots of different directions that question can go from. Like, what do you share of your personal life at work when these are kind of personal questions, but then also just functionally and practically like have these conversations with your team. How do you have these conversations with people that you’re hiring and to try to help discern if this is a good cultural fit for them? And those kinds of things.

I’m really curious about just how your approach to work is manifested in your organization.


First thing is that as leaders, we have to model the behavior that we’re looking for and getting comfortable with that practice of modeling. Things like transparency, vulnerability, willingness to fail, showing our learnings and growth over time.

That has to be present because if you as a leader are not showing that you act on what you say you believe in, people watch what you do way more than they listen to what you say. You know, they’ll listen to what you say, but they want to see it in action for them to really believe that it’s safe for them to follow suit.

But organizationally, one of the most important things to me is and always has been a clearly defined mission, vision and values. It can sound like one of those hokey topics that you might waste a lot of time on. But the only way you waste time on that is if you don’t follow through on it. For us, getting that on paper and putting it front and center in our hiring process in the way we make decisions, in the projects we take on, it’s made that our reality, our mission is to help creators earn a living.

Our vision is kind of a four or five part vision on us becoming one hundred million dollar a year revenue business on our creators who we serve, earning a billion dollars a year in their businesses of us staying fully remote, fully independent from investors keeping a small and efficient team. If you look at our vision, you know where we want to be five years from now. And you know what you’re signing up for when you walk in the door. And then if you read our values, you can see how they play out and the way we operate.

I can’t tell you the number of interviews I’ve sat in on or conducted myself with potential teammates who have said, you know, I have questions, but honestly, it’s just drilling down into details that about things that I already know about the company because you are so public in direct about what you believe. So I think defining that, putting that on paper and then actually living by it is crucial that creates an environment where people know what they’re getting into and they know why they’re getting into it, because they share those beliefs.

And then there’s all of the kind of cultural habits that surround that mission, vision and values. So an example of this, twice a year we do team retreats where a fully remote company, I guess that’s the first thing that you would have to know about our culture, is that we don’t work in person and we never have and we don’t plan to. But we know that deep and meaningful relationships often need a physical place to form. So we do twice-annual team retreats in person right now.

Obviously, those are on hold because of the corona virus in there.

We have some really intense little habits. One of them is that we do breakout activities, right?

We talk about strategy and ideas and in all of these kinds of things, just like any normal company would. But we very intentionally put people into groups together who don’t work together often so that they connect with one another. Another exercise that we do. Across the organization at the start of every meeting, but also in person, is an exercise called red, yellow, green. We ask every person, how are you doing? And it’s like the how are you doing?

Really question. So that we know the context that everyone’s entering into a conversation with. If you’re red, you’re not doing well and you share something that’s going on in your personal life. We know to give you a little more leeway, give you a little more forgiveness and grace during this conversation. Whereas if everyone comes in green, we know, OK, great, then we can. This can be one of those where we can conflict over ideas and bring our best thinking and really go at it to end up in the right spot without it being feeling dangerous to anyone or unapproachable to anyone.

Another exercise we do is something called Listening Walks. A couple of these things we’ve gotten from a coaching organization we work with at the leadership level called Reboot, which is run by Jerry Colonna, fabulous leadership book called Reboot as well by Jerry and Listening Walks are these 30 minute exercises that are built around a single question not dissimilar to the one that you open this conversation with? It could be something like how did you end up back in Birkitt? Another one we’ve done is what is something that you wish more people knew about you as a professional?

And the way the exercise works is everyone gets a partner. We very much encourage people to choose a partner they don’t know very well in the team. And you go outside and you go on a walk and for 15 minutes you walk one direction and one person’s job is to listen in. The other person’s job is to answer the question. The listener does not speak for 15 minutes.

And then he reached the endpoint and you turn around and you switch and we all come back together and we sit in a big circle. And if your partner is giving you permission, we share our takeaways from that conversation. And it’s in those kinds of moments where people learn number one about each other and number two, that they can show up fully, that they can share themselves. They will be seen, they will be heard, and they will be appreciated for who they are and that everyone else is doing it, too, that it’s not this big.

I mean, it is still risky. It feels risky, but it’s less risky because everyone is in on it. Everyone’s committed to that kind of transparency and environment. You know, that’s one small example of many, many habits we try and build as an organization that allow people to show up. And it doesn’t mean everyone’s gonna fit here because there’s some people who wouldn’t fit in that kind of environment. They wouldn’t want to be here for those kinds of exercise.

Maybe they feel like it’s childish or it’s too vulnerable or they’re just here to work or whatever, and that’s fine. But for the people who are here, that kind of stuff is very meaningful.


Yeah, I love it. Yeah. It’s just very cool to I mean, I can’t imagine being a part of the organization, but, you know, with that kind of intentionality, it’s really it’s really amazing.

It’s inspiring with the values and vision. I guess I’m curious, at what point did you join convert kit? And I guess my question was gonna be, did you were you a part of crafting that mission values, vision, values maybe that the predecessor of that question is, at what point did you join Convertkit? Then, I’m not sure that we even really highlighted that transition from Fizzle to Convertkit. Yeah, yeah. Be a little rewind there and then back to that question.


Yes. So there came a time at fizzle. I want to say it was maybe three years in, almost three years in and. I was growing quite a bit and I was excited about the work we were doing, I had a lot of ideas about where we should go, how we should operate, how fast we should be growing, and those ideas, I think we’re out of alignment with some on the team there. Ultimately, I wasn’t a founder of Fizzle.

So these were just an employees ideas at the end of the day. And because they clash with at least one of the founders, that meant that eventually I just needed to leave. And looking back, there was a really painful departure at the time, but I think it was the right move for me. And so I came in to Convertkit. About three years after it was founded. For the first two, two and a half years, it was pretty much a side project for Nathan, our founder.

Nathan was already a dear friend of mine. We met at a conference called the World Domination Summit. In 2012, I joined the company in 2016. So we had been friends for years at that point and we had been in a mastermind group together. We had been meeting every week for years. We had gone on retreats with that group. So it was it was kind of just like joining one of my best friends in business, which is risky.

About three years after it was founded, I was, I think employee number 17 or something like that. We now have about 60 people on the team four years later and we did not.

We had ideas about what the company was. I’d kind of been an advisor from the early, early days, but there was no defined mission, vision or values. And so it’s both true that I joined later than other people and that I got to be involved in forming it, putting it on paper what it was that we were going to be about, how we were gonna operate from then on. So that’s the basic answer there.


Yeah, that’s great. Was there a gap between Fizzle and Convertkit for you?


Only like a month. Yeah. Nathan had been recruiting me for a while to try and join the team and I had kind of rebuffed them a couple of times and was happy with the work I was doing.

And so then when it was time to move on from physical before I had even really looked at anything, Nathan and I had been in conversation and it just made sense to come over.

How long it meant for people who were listening that just really, really stuck .

And I know we already touched on some of this, when it comes to that misalignment, you know, a lot a lot of people listening are there in a place where there something isn’t quite right with work, but they’re not always sure what that thing is.

I’m curious if there’s just practically no way that there’s any whether it be words of wisdom, encouragement, or even just like here is an activity you should try if you have anything that you’d like to say to them?


I’m going to run through a framework that I’ve been thinking through. And the exercise would be, as you hear these eight things that I list, ask yourself which of them are missing in your career or in your job that you’re in right now. So there’s eight things I think contribute to meaningful work. It may not be exhaustive and this may not be exactly right, but it’s a working theory. So the first thing is to have meaningful work. You have to be solving an important problem, solving an unimportant problem in an important way.

Think of an important problem as something like society level solving for racism or hunger or climate change or something like that. Unimportant problems or things like we’re solving in Convertkit. Relatively speaking, we make email marketing software. I have no misconceptions about the degree to which that is changing the world on its own.

But I think the way we operate and the way we run the business is important. So that’s the first one. The second one is your work should align with your essential or core beliefs about the world. Now, to know whether your work aligns, you have to know what your beliefs are. That’s what I was getting at earlier. The third one is that you should be surrounded by people you trust and respect and who trust and respect you. And I think a lot of times it’s actually that one that really gets us is the people are a lot of the problem.

Number four is we are given the freedom to fail. And I think the key here is it’s not like make the same mistake over and over, but you’re allowed to take risks. And if they don’t work out, you’re not going to be fired on the spot. The flip side of that is that you’re also pushed to grow. So there’s a different stream gift being given the freedom to fail versus taking that freedom and using it to really grow as an individual.

So I think your work has to push you to grow. You’re not being pushed to grow. I think it’s really hard to find meaning. I think you were cast to allow for a base level of financial security. That’s number six. If you can’t put food on the table, it’s that base level of Maslow’s hierarchy and maybe the next level up of having love, food, shelter, you know, physical health. If you don’t have those things, nothing else matters.

And I think finances helped provide for a lot of that. Seven is I think meaningful work has to happen in an environment where people are treated equitably and where they are given credit, where they deserve it. Too many organizations play favorites. They have clicks. They have politics. And when you see that stuff happening and it’s passing you over, especially when you’re deserving of more credit or more recognition for the good work you do. I think it’s really hard to find meaning on an ongoing basis.

And then the last one is. That there’s transparency. Is there transparency in your workplace? Do you know what’s happening in the business? Do you know the financial state of things? Do you know who’s going to be hired? And do you know what those strategic priorities are at the organization and why you’re pursuing them? I think in the absence of transparency, we tell ourselves stories and many times when we have to tell ourselves stories, in the absence of information, we tell ourselves the worst version.

So transparency combats that in my opinion. And I think it creates an environment where everyone can show up and not have these fear signals out all the time of what should I be watching out for? Because you already know what’s going on. So those are the eight. And I’d just say write them down and ask yourself, are these things present for me? And if not, which ones are missing? And I think that might start to highlight some of the gaps that you’re looking to fill the next time you go try and find a job.


I love it. I love it. I’m curious, you know, for people who are finding these gaps and I’m going through and I’ve read some of this on your e-mails before from your blog. So this isn’t my first time running through this matrix, but I know it is for everyone listening. How much of this means person needs a new job? How much of it means. And this is I’m processing this as I’m asking that it could just be a different approach or different way of showing up in your work.

I’m curious if you have thoughts on that.


Great question. I don’t think it always means you need to change jobs or organizations even. I think there’s different levers you can pull. So one is change yourself and keep everything else the same. Sometimes it’s all it takes. You just have to change your approach. The second thing is sometimes you need to ask for something in your current job, in your current organization. You need to ask for change from your manager or your team or your organization as a whole.

You might get a no back from that, and that might put you back to the next one, which is finding another job. Sometimes, though, you can find another job within the same organization, depending on the size of it. And that might fix some of what you’re experiencing. The last one would be or maybe the next lesson would be, go find another job at another organization and start from scratch. But the final one is sometimes you just you’re not wired for that. And the actual gap is that you need more control over your path than other people. And I think that’s where you end up getting started doing your own thing. You become a creator. You become an entrepreneur. And I think that’s an option, too. And so there’s this wide range of possibilities there. And it’s very rarely true that the answer is immediately, well, I better go find something else. It takes more examination than that.


Yeah, great response. I think too often we default to. Yeah, well, this isn’t work. I need a new job. And I think that’s a great I think even a great hierarchy to change yourself or your approach or your mindset. Ask for change. Find another, you know, role within the organization. Then think about leaving or you’re for another job or starting your own thing. I think that’s a good hire of a process. You don’t jump ship till you know the one you’re on wants sail to where you want to go.


Exactly. E.xactly


Yeah. It’s awesome. Very cool.

Well, just as we move towards wrapping up. I’m curious if there’s anything that I haven’t asked you related to this topic that I should. I know that you’ve done so much work around this, both personally, but organizationally. You’ve put in your time, you’ve put in your writing. Is there anything that I’m missing from this conversation that you’re like it’s right there. I just want to share it. And the answer could be, no,


There wasn’t anything before you said that. But as you said it, I realized that one point I think maybe people gloss over related to all of this. I’ll use a kind of metaphor. You see people all the time saying if you don’t like a book, stop reading it. I think it’s really bad advice and a lot of cases. Interesting. If you picked up a book for the right reasons because you think it’s going to teach you something, it’s quite possible in the middle of that book, you’re going to hate the process, that it’s going to be hard.

Maybe it’ll challenge you. Maybe it’s above your comprehension level. Maybe the topic isn’t what you thought it was. I think there’s a lot of value in finishing a book. He picked up for a good reason because it might teach you something that you didn’t want to learn, but that now reveals something that you didn’t previously know to be true.

So if I parlay that to work every day is not going to feel like a cakewalk. It’s just not that’s not how meaningful work works. A lot of days are going to feel really hard, really frustrating. It’s going to feel like you’re trying to create change you care about. And it’s not happening fast enough. And then you’ll have little moments along the way where you take a step back and you look around and you realize, wow, I’ve come a long way.

It’s not going to feel like that every day, though. And so I would just make sure everyone listening remembers meaningful work is not easy work. It’s very hard. Maybe the hardest kind of work you can do. It’s the riskiest, too, because you’re really putting your emotions on the line to care is to take a risk. But I don’t think there’s a risk more worth taking than caring to try and do meaningful work. And so just recognize that it’s a long arc and you’re going to be frustrated along the way.

And I think having the resilience and the grit and the wisdom to take a step back and say what’s the right next step? Knowing that every day is not supposed to feel easy.


Wow. I feel like everyone listening should just rewind the last, like two minutes there and listen to that again. And what a great thought for us to end on. It’s never easy and it shouldn’t be. But it’s worth it. And so thank you for that.

And thank you so much for the time here. It just really, really great to connect. And I know that there’s so much that listeners will be able to take and put, you know, into action in their own lives. So really, really appreciate everything that you’ve shared.

So if people are listening and really resonate with this conversation and with how you think about these topics, is there anything that you’d like to invite them to? Yeah.


You know, I love sharing just because I love sharing. But you did ask me this and I thought that I’m very bad at promoting myself sometimes, so I figured I’d take the opportunity to do that.

I love running Convertkit. It’s where the majority of my time goes. And I still look at myself at my core as a writer. I mean, that’s my core identity as a professional. I just happen to exist within an operations role. So my writing happens at And the framework that I kind of walk to those eight factors that contribute to meaningful work is the entrance into my work that I give everyone who joins my email list. So I guess I’ll co-promote Convertkit and myself at the same time by saying if you want to hear more from me,

That’s just a Convertkit landing page I put up where you can join my list and you’ll get that 10 day series about what contributes to meaningful work. My first name is two “Rs”, two “Ts” as well, in case that’s a little confusing.


Love it. Love it. And I’ll make sure to link up to that in the show notes as well as to Convertkit, which I love and thank you for building such a cool product.


Thanks, Dan. Appreciate you having me.


Yeah. Thanks so much. I really appreciate it.

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