Building Grit Through Community with David Shriner-Cahn

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Join me today, David Shreiner Khan on Hot Habits with Dr. Tamsin.

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David has created an award-winning podcast in community, Smashing the Plateau, for solopreneurs.

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We talked about why work-life balance is a misnomer, and why making decisions that you've made for years in corporate can be really difficult to make on your own.

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We looked at the invisible architecture that is lost once you leave an organization and dug into some of the juicy research on grit and founders.

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Your nervous system sets the tone.

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Your energy speaks before you do.

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How you show up is the culture.

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I'm Dr. Tamsin Aster, and this is Hot Habits, conscious leadership in action.

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Hello, hello, and welcome to Hot Habits with Dr. Tamsin, Conscious Leadership in Action.

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My guest today is David Shreiner-Khan, an award-winning podcast host, community builder, and self-proclaimed corporate refugee who spent decades helping ambitious professionals make the leap from corporate career track to actually owning their own damn business.

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Forbes calls his podcast, one to power up your ultra lean business.

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Inc. Magazine said he'll change the way you communicate.

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Oh, that's super juicy.

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But here's the thing that I love about David.

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After all those years helping people build solo businesses, he's landed on this one gorgeous paradox.

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You can't do it alone.

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So he built Smashing the Plateau, a community where solopreneurs get matched into small trusted pods and show up for each other every single week.

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David and I didn't meet in some random LinkedIn DM.

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We met through a mutual friend and we bonded over the fact that we both enjoy long walks at Wave Hill in the Bronx.

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Looking out at the Hudson, wandering the gardens, doing the thing that you have to do if you live in a city this busy.

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Find the green, the quiet corners and take some time to breathe.

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So please welcome David Shreiner Khan.

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Thank you, Tamsin.

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Great to be here.

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So at the start of every hot habits conversation, I asked my guests to bring an object with them, something that represents a hot habit in their life as a way of bringing leadership out of theory and into everyday reality.

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So tell me, what object did you bring today and why did you choose it?

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So mine is pretty simple.

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If you're watching the video, I'm lifting it up.

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It's my microphone.

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And I like asking questions.

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And the feedback that I get from people is that I ask good questions, which maybe explains why I like podcasting and podcasting.

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I've been doing it now for 12 years.

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So we have just crossed our 1,000th episode recently.

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But I get good feedback from people I interview as well as from members of our community when I ask pointed questions.

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Awesome.

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I love that.

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And because I think what you're reflecting here is the chemistry between people, right?

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There's something about being asked a question.

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And I know that from the appreciative inquiry community that I'm in exchange, which, you know, the whole model of appreciative inquiry created by David Kuperider started with this idea of how you ask questions changes the response you get changes the way people understand their experience.

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So I love that you've started with that framing.

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I think the thing that I find interesting about what you do is in our world, particularly in America, there's a real thrust of independence.

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Like we can all do it on our own.

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When people jump from being in a more structured organization in a corporate career and start to work for themselves, there's this sort of often this initial sense of like, wow, freedom, I can do it all my own way and create all my own systems.

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And then there's the reality of, okay, now I have to do all of that myself, right?

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And it can easily become this sort of echo chamber.

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within ourselves, right?

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So why do you think it's difficult to make good decisions when you are working on your own, even if you've had decades of experience doing it in an organization or with other people?

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Because that echo chamber is what feeds your own difficulty making decisions about actions that are going to move you forward.

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So, for example, if you have a long corporate career, let's say you leave your last job and you're mid-career, so maybe you're in your 50s, and you're in a place where –

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you have some kind of leadership role.

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So you probably have, before you've left, you probably have a full calendar, an overflowing inbox, a team of people to take care of all the things that you're doing.

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not responsible for doing yourself.

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You have this built-in social network of people you can bounce ideas off of.

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You get informal feedback as well as the formal feedback.

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So this whole both formal and informal structure that helps you and others in the organization make effective decisions that will...

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help the bottom line of the enterprise.

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And then you go out on your own, and yes, you have this great sense of freedom, but you start off with an empty calendar, an empty inbox.

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There's no team of people that you're interacting with

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Not only for them not to do things that you either aren't so good at or don't want to do, but there's nobody to bounce ideas off of.

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And then the most important thing as a business owner is you've got to market and sell.

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And if you're doing this, if you're a professional service provider, which is what is important,

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the common thread in our community.

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If you're a professional service provider, you've got to market and sell yourself, which is something you probably haven't had to do before.

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It's certainly not in this way.

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And it's quite daunting.

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So it's like, okay, so what do I do first?

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Do I...

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Do I need a website?

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Do I need a business entity?

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Do I need to spend my time prospecting on LinkedIn versus...

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networking versus cold calling versus mining your warm relationships.

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Right.

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So what ends up happening is there's a lot of spinning that goes on inside your head and particular the things that might be the biggest points of leverage.

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Yeah.

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Yeah.

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could be the ones that cause the most anxiety for you to actually do.

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So, for example, I've seen this in our community.

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We have members whose 90-plus percent of the business comes from warm relationships, right?

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So if they set up a structure where they just spend time reaching out to people who already know them well, who know, like, and trust them, and if they're in a position to make a referral or feed them some business, they would do it.

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So all the person has to do is...

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pick up the phone and make a call, send them a note, schedule a Zoom call, whatever it is, meet for a cup of coffee.

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They're often really afraid to do that.

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So it sounds to me like there's this sort of the invisible infrastructure piece, right, is part of the conversation here that you're alluding to, is that when you leave corporate,

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a lot of the decisions about the infrastructure, who's doing what when and how is it done is suddenly removed, right?

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And so then the question becomes where to put the time and energy on, you know, the operations, the development, the marketing, like we tried to wear all the different hats.

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And the fear piece around it, when you're not under the umbrella of somebody else, it sounds like that a part of what you're saying in, in that last piece is how do we get at working through the fear?

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And I was reading an interesting op-ed by Angela Duckworth, the grit researcher in the Atlantic this week.

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And she pointed to research showing entrepreneurs actually do better when they're brought together to learn from each other.

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So yeah,

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The research seems to suggest that when you bring entrepreneurs together and they're not left to grind it out solo, and they really are in an intentional space like what you've created with Smashing the Plateau, they do better.

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And she gave some research...

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by Paul Graham, one of YC's founders who said, even if you could do all the work yourself, which is what you were alluding to with, should I be the chief marketing officer today?

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Should I be doing, being the chief financial officer today?

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Should I be calling people?

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Like this sort of blurred focus with the lack of structure that we find ourselves in, right?

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His suggestion is that we need colleagues to brainstorm with and to talk us out of silly decisions and to cheer things up when we go wrong.

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And he has actually taken the approach that funding co-founders is actually a better way to facilitate success.

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So if we think about grit as being partly built by community rather than found within a person,

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What habits build more grit?

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Pushing harder alone or showing up in a room of peers every week?

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Well, honestly, I think you need to actually do a mixture.

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So there are certain things you do need to, like, they're better if you just kind of dig in your heels and push at it.

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You know, for example, if you're writing content, right, and it's your ideas and your experience, then you're probably better off doing.

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buckling down and doing that alone.

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But if you're working on a new idea, or you're trying to understand how to deal with a difficult client, or you're trying to understand what has changed in your marketplace, if you're suddenly not getting leads the way you used to, or you've changed your offer and you're trying to figure out why it's not working as well as

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you had hoped.

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A lot of these things, it's kind of natural to bounce these ideas off of other people.

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And it's kind of interesting.

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One of the things I hear from our community members is it's not just the feedback that they get from peers, but just the act of having to

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share what they're working on every week.

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And when they try to articulate what they're working on before they even get any feedback, that already changes how they view it, right?

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There's something about the mechanics of explaining a challenge or explaining something that has already happened that can make a difference in how

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you think about it.

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So the first step is just kind of repeating in your mind what has occurred, what's worked well and what hasn't worked well, and articulating that to trusted colleagues.

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That step alone is worth a lot.

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And then what happens once you have finished speaking and you hear from other people, that's like another step in the process.

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I find that really interesting because I know that, you know, having been, you know, in academia and taught, right, and shifted now into the world of facilitating and speaking.

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Um, so one of the questions I have for you, particularly because, you know, some people, um, struggle with feedback in your community, David, when somebody shares and gets this great experience of like the verbal processing, the sort of moving it and the way I talk about it, moving it from the kind of internal subjective swirl out into the world, whether that first step is onto paper and then out to other people and, you know, feeling their response to it.

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Do you have a sort of formal structure for how you encourage your community to give feedback so people can actually take it and implement it?

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Because one of the things that I see often with leadership and organizations and teams that are struggling is that those that place of being able to hear each other.

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Is where we often get stuck.

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And I know that communication is one of your strong suits.

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Yes.

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So one of our ground rules is confidentiality.

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So what gets shared with your team stays with your team unless the person who's sharing it gives express permission for somebody to share it elsewhere.

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So that's one.

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Because you need to trust that if you make yourself vulnerable by sharing something, that it's not going to go haywire.

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So that's one.

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ask questions first that will help understand what's going on a little deeper.

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And then the second is to share your, an experience that you may have had that might relate to what the person who has shared something is going through because we,

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What needs to happen in the team is a feeling of not being judged.

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And when you give advice, it can come across as being judgmental.

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Whereas if you share an experience and they're like,

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I face something that I think might relate to this.

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Here's what happened and here's what I did.

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Then the person who's hearing it can either decide this is relevant to my situation or it isn't, or maybe this piece of it is relevant and other things are not.

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So that's another way to do it.

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The other thing that's important is having a facilitator who guides the discussion.

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Because even with the best of intentions, things sometimes go haywire.

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We had a situation recently where a member shared something they were working on where they were really struggling to kind of get this new thing out.

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And it was the first time they had shared...

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a bit of the process with others, which, and on the surface, if you weren't involved in the process, it didn't seem all that weighty.

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But for the person who was working on this new, new project, there was a lot of emotion tied into actually getting the project launched.

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And,

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Some people gave feedback that was very encouraging and super helpful.

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And the encouragement, because of the emotional barrier to getting this project launched, the encouragement was really valuable.

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There were a couple people who gave, I would say it was more like advice that was very tactical and very logical and didn't connect with the emotion that the person struggling with the project launch was feeling.

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Person was like, whoa, did I share too much?

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Is this the wrong team for me?

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All kinds of things happened.

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And as the facilitator, I then needed to have some one-on-one discussions with the person who did the sharing, with the people who provided the feedback that wasn't taken so well.

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And things got patched up, but it didn't happen on its own.

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Mm-hmm.

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So, I mean, what I'm hearing almost is there's this sort of difference between asking for advice and helping other people, you know, or asking other people to help you think better.

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Right.

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Because we know the research from Nancy Klein says that when somebody is giving you full attention, right, the quality of your thinking changes.

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Right.

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So it sounds like.

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there was almost like a sort of breakdown here in was the person asking for advice or were they just asking people to help them think differently?

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And when you create your teams, do you think through and make explicit the difference between like the thinking versus the advice?

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Yes, and I'll reiterate it every so often.

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It also, it's something that as teams mature, these habits develop naturally.

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Mm-hmm.

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So you don't always need to be super explicit with people about how to interact.

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But you do need to guide them.

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Mm-hmm.

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Success is a state, not a symbol.

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Most of what you're calling ambition is just cortisol with a calendar.

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In the show notes, grab the free video and worksheet to build habits around the state of success, not the symbols.

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Real success isn't the title, the income, the abs.

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It's the capacity to actually be present for the life those things were supposed to buy you.

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Get the link in the show notes.

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So when you create these teams, do you group your teams in a...

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way that they have particular overlapping past experiences, that they are growing an organization or a new business that is product oriented or teaching or sales or like, like, do you how do you do that?

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Because one of the things I'm really interested in is how a lot more research is coming out that suggests that

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the more diverse teams are, they do better.

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Like when you have different ages and perspectives and gender and all of those different pieces that play into it, we have different views and skill sets and ways of understanding the world and we can get to the solution.

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But that tends to be within the same organization, like with the same mission, with the same vision.

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So as I was thinking about our conversation, I was wondering about how you grouped people and how intentional it was in terms of similarity versus difference.

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Well, the people are definitely different.

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I think about it kind of like the way a president might choose members of a cabinet.

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Mm-hmm.

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And also, we've seen this with corporate leaders who choose their management team.

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Mm-hmm.

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There are some people who just want an echo chamber.

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Mm-hmm.

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Who select people who are very much like themselves.

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who have experienced like themselves, think like themselves, and they don't want people who are gonna push back.

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And then there are others who in particular look for that diversity, look for people who will challenge them, look for people who push back, and they wanna be the dumbest person in the room.

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Yeah.

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And honestly, I think that produces a much better result.

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Right.

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Right.

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So I think about it the same way that diversity helps.

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I can't always tell going in how well people are going to fit.

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There's.

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There's probably less logic to this and a little more intuition because I've been doing this in various ways throughout my career.

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Yeah.

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I've been in leadership roles for most of my career.

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So it's...

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I don't know, there's a feeling to how people may fit together and may gel.

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And sometimes you may put somebody new on a team and it doesn't work out so well.

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And then you've got to make a change, right?

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Just like you would if this is all inside one organization.

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If you're doing it where we're dealing with each person is his or her own organization, right?

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it's really the same principle.

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If, if a new team member doesn't fit well, you've got to make a change and the sooner you do it, the better.

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Yeah, no, I like the way you've sort of described it as like the science and the art, right?

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Because when I first, you know, went out on my own and started thinking about employing people, I definitely went through the cycle of hiring people who were like me and then it not working out and then hiring people that are too different from me and not working out.

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And, you know, I worked with one business coach for a while who suggested that we use like Colby or Clifton Strengths or some kind of marker to say, you know, you fall in this category.

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So having somebody who complements that is a useful way to think about it.

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And that works for a little bit.

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You know, I'm a you know, I'm an activator.

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I'm a starter.

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You know, I like to gather information, but I'm you know, I'm not high on the execution on the follow through.

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Right.

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And so that's not my natural skill set.

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And I do it better when I'm in a team with other people.

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Right.

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So that worked for a little bit, but it but it also sort of pushed me into like, again, thinking in the head and not listening to the body, the intuition, the the past experience.

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And I think one of the places that I find so interesting about the world we're living in right now is how much artificial intelligence can do a lot of that for us.

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Either build the agents to do the work for us, right?

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Or say, this is your skillset, you need to be matched with somebody with that skillset.

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But it doesn't have that right now, maybe it will, that intuitive sort of felt experience that is cultivated over years.

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So in your experience of running communities and, you know, the work you're doing, right?

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What this sort of realization makes me think a little bit more about is, you know, the conscious leadership, which I define as, you know, are you aware of the impact, right?

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And when we are taking the lens of conscious leadership and doing the inner work, right, the meditation, the journaling, the self-awareness, the thinking about how we're showing up in reference to others...

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What you've done a lot of, and what we've talked a lot about here, is what I might call relational infrastructure, right?

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How do you define that in the way you work in your community?

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Well, it's an art and a science.

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Right back at me.

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Yeah.

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I'm not sure that I have a good definition.

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What I observe is when it works, people show up.

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Right?

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We have a high attendance rate.

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We have very low churn from members.

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And when a member is going through a really tough time, other people will show up.

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And sometimes the tough time is not business-related.

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It's personal.

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Right?

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There could be...

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an elderly parent who is going through health issues or, you know, sometimes we've had members whose parents have, have died and they've been super involved in caregiving towards the end and dealing with, and then dealing with,

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estate issues and you know all this stuff um takes time and energy and if you're a solopreneur it has a huge impact on your business or can have a huge impact so how do you like keep the ship running while you're dealing with um personal stuff that is really difficult um sometimes we've had we've had members who have been dealing with

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caregiving of elderly parents and children simultaneously.

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The sandwich generation, yeah.

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Right, which is, particularly since a lot of our members are, I'm going to say like the 50s and 60s, this is a common theme.

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Mm-hmm.

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So we may have sessions where the topic of discussion is not how do you maximize revenue and how do you get a new client in the door or how do you negotiate a deal.

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It may be how do I manage to keep my business going while I'm dealing with all of this personal stuff that is taking a huge amount of effort.

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Yeah.

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I love the acknowledgement of the personal.

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I find it frustrating when people try to separate those out into sort of two distinct worlds as if they don't impact the way they flow together.

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And I have seen a lot of struggles in the sort of founder startup, work from home, entrepreneurial community

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I really saw it really blow up a lot during COVID, right?

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Particularly for women who were really struggling with trying to be a teacher and run a business and run the home.

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Not only trying to have all of those roles at the same time, but in the same space, right?

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All on top of each other, which created, you know, for so many people, a really difficult time.

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And I think,

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One of the things that I've noticed as I've started to move into the stage with my kids leaving home and being able to take more control over my time is thinking a little bit differently about what it means to be productive, right?

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Because...

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One of the things that I notice in the transition between being in the Europe and being in the US and I've spent half my life in the US is the vacation time and the social structures for support and the kind of the village raises the child community like a little bit more of those energies in Europe versus the US.

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One thing that I wonder is, you know, most leaders will often think about, you know, prioritizing their workout, prioritizing, you know, time for, you know, being productive, right?

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Doing the things that we're told is gonna make us productive, right?

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Getting up at five, doing the meditation, going for the run, checking the boxes.

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But there's something about scheduling time with the thinking partner.

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Right.

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So what does that priority order say about what we've been taught to divine productivity?

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Yeah, well, Tamsin, think about the phrase work-life balance, which I think is a terrible way to describe what you're trying to accomplish, because what it means is that something is always going to be embedded.

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Out of balance.

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I much prefer to talk about work-life integration because you are one whole person and you're dealing with all kinds of stuff all the time.

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And you're trying to get it to integrate as much as possible.

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And the better you're able to integrate things, the happier you're going to be.

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And the less stressed you'll be.

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What's your biggest tool or habit that you promote, suggest, advise, encourage your community to commit to, cultivate practice that helps with integration?

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I like the philosophy behind the one thing.

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Yeah.

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which if you're listening and you're not familiar with it, just search for the one thing.

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It's a philosophy.

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There's a book.

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There's a whole movement behind it.

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But the whole idea is that there are a small number of...

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of areas that are important to you in your life, right?

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So there's work, personal, family, relationships, spiritual issues, physical health, et cetera.

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There's a small number of these.

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And in each of these areas, you can identify one primary

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focus that is the most important thing to do right now.

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And if you think about the 80-20 rule, where 20% of your effort leads to 80% of your results, if you break up your life into these quadrants, quadrants is probably the wrong description, but these areas, you'll probably come up with like six to eight main areas.

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And if you pick one important thing,

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that you're going to focus on.

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And I would suggest if you're trying to make any kind of change, this is what we do in our community, pick one thing that you're going to work on over a period of time.

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Maybe one primary thing you're gonna work on for a quarter, for three months.

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And then break that down into

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small, very small activities where you're going to have one activity in that area per week that you'll work on, that if you make any kind of progress on it, it's great.

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And not to worry about the other things because there, it's like you're looking for that point of leverage.

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Yeah, no, and I definitely know that having worked with people for years around habits is people often get really excited when they start on the journey.

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They want to change everything, right?

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But then we don't have the follow through.

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So what I've always appreciated about that framing is to, you know, put some boundaries around it, right?

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Because habits really are structure, right?

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Right.

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They are structure that makes life easier.

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And the more you can create a structure that supports you and is in alignment with what you are building, what you care about, what you've identified as the thing that is really important to you at that time, it does make it a lot easier to keep going.

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This has been such an interesting conversation, David.

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I think one of the things that I'm really enjoying listening to you and like thinking about like the theme of our conversation, the arc of our conversation is the dance between the working alone and community.

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A little bit like some of the conversations I've had around doing the inner work and then going out into the world and going, how do you feel?

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do my relationships change when I have slept better, when I'm meditating, when I've gone to therapy, when I fill in the blank, right?

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So this dance between you have to do a lot of this work on your own and being in community with others fundamentally shifts.

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how you show up and creating the right kind of structure, the right kind of habit, the right kind of mix within the, within the community, which includes having really important conversations and frameworks and rules for want of a better word to support feedback and kind of distinguish between, you know, advice and a kind of thinking space.

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When we,

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think about how this impacts people in the world and like what you really care about, what's the thing that is most important to you?

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What's the insight, the action, the kind of big driver that keeps you going and pushes you to daily take action towards this goal of smashing the plateau

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And in that, and I know this is a long question, I'm sorry.

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And in that, what is an action that people can take away based on why you believe this and what people are doing in the world?

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Does that make sense?

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Yeah, honestly, it's the little things that happen along the way.

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So if we have a team session and I see that,

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Something that happened in the previous session has made a huge difference in the following week for one person.

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That's so satisfying to know that the process actually makes a difference in people's lives.

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What's one thing that you used to believe about leadership that you don't anymore, David?

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Well, early in my career, I probably only knew about the sort of command and control male leadership that was a model.

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There are lots of other ways to lead.

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And is that the other ways to lead?

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Is that something that you encourage your community to lead into and lean into as in learning different styles of leadership depending on the situation?

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Or is it more about acknowledging your own leadership style and working with that?

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How do you view that?

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I would say it's more acknowledging your own leadership style, what works best for you.

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And...

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You don't necessarily need to be in a formal leadership role leading a team to be an effective leader.

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So, you know, in particular, a lot of our members are consultants, solo consultants.

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Well, if you're a consultant...

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working with a client, you're not really formally leading a team.

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But, um, if you are doing things like just communicating effectively with the people on the client side,

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that are supposed to be taking action based on your work, just that act of communication over time can make a huge difference in the outcomes for the client.

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Right?

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So communication and effective communication, particularly in our world where there's so many different ways to communicate,

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Um, effectively communicating and closing communication loops with people is like so important and it's something that people who are really effective at consulting do well.

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I love that.

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Well, thank you so much for joining me today on hot habits with Dr. Tamsin, you can find David Schreiner-Kahn at smashing the plateau.

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Do you have any final words you would like to share?

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If you're interested in learning more about how effective you are in managing some of the different elements of your life and work that we discussed today, we do have a free self-assessment you can take, which is at smashingtheplateau.com slash clarity.

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Thank you so much.

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Thank you, Tamsin.

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Thanks for being here and thank you for taking the time to listen.

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Until next time, remember that the way you lead your inner world shapes how you lead on the outside.

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I'm Dr. Tamsin Aster.

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Thanks for listening to Hot Habits.