If you’re out there making it on your own economically, the depiction of entrepreneurism in the media likely has you scratching your head. Everyone other than you seems to have their act completely together, right?
Unemployable has been calling BS on that narrative for almost three years now. On this show, real entrepreneurs tell you how it really is, and it’s often not all that pretty in the stages leading up to success (and sometimes even after success arrives).
Another common misconception is that entrepreneurs have to transform into something they’re not in order to find that success. In reality, the way it works is that you honestly assess exactly who you really are and play to your strengths.
That’s why I’m excited about this episode. We’re welcoming psychologist Sherry Walling back to the show, and this time her husband Rob Walling — the serial entrepreneur who founded email service Drip — is joining her to provide a pragmatic example of the entrepreneurial psyche.
The Show Notes
- Zen Founder
- The Entrepreneur's Guide to Keeping Your S**t Together
- Rate/review Unemployable at Apple Podcasts
Know Thyself: The Entrepreneur’s Secret Weapon, with Sherry and Rob Walling
Rob Walling: I'm Rob Walling.
Sherry Walling: And I'm Sherry Walling.
Rob Walling: I'm a startup founder.
Sherry Walling: And I'm a clinical psychologist.
Rob and Sherry: And we are unemployable.
Voiceover: Welcome to Unemployable, the show for people who can get a job, they’re just not inclined to take one — and that’s putting it gently. In addition to this podcast, thousands of freelancers and entrepreneurs get actionable advice and other valuable resources from the weekly Unemployable email newsletter. Join us by registering for our Free Profit Pillars Course, or choose to sign up for the newsletter only at no charge. Simply head over to Unemployable.com, and take your business and lifestyle to the next level. That’s Unemployable.com.
Brian Clark: If you're out there making it on your own economically, the depiction of entrepreneurism in the media likely has you scratching your head. Everyone other than you seems to have their act completely together, right?
Unemployable has been calling BS on that narrative for almost three years now. On this show, real entrepreneurs tell you how it really is, and it's often not all that pretty in the stages leading up to success (and sometimes even after success arrives).
Another common misconception is that entrepreneurs have to transform into something they're not in order to find that success. In reality, the way it works is that you honestly assess exactly who you really are and play to your strengths.
That's why I'm excited about this episode. We're welcoming back psychologist Sherry Walling to the show, and this time her husband, Rob Walling — the serial entrepreneur who founded the email service Drip — is joining her to provide a pragmatic example of the entrepreneurial psyche.
I'm Brian Clark and this is Unemployable, solid professional advice for freelancers and solopreneurs. Thanks for tuning in, and if you enjoy the show, please help us out by leaving a quick rating or review over at Apple podcast. You can go directly there by visiting Unemployable.com/iTunes.
Rob and Sherry, Sherry and Rob? Not giving any preference to my first dual guest podcast ever here on Unemployable. How are you two doing?
Rob Walling: Doing Great. Thanks for having us on.
Brian Clark: Sherry, does that mean you're not doing great?
Sherry Walling: Yeah, isn’t that awkward? Like, “Is he speaking for both of us?” Yes, I'm doing great.
Brian Clark: No husband ever should speak for both.
Rob Walling: It's not for the record.
Brian Clark: At least that's not my experience.
Sherry Walling: It doesn't usually work out that well.
Brian Clark: Exactly. All right, so you two are in balmy Minnesota. And from what I understand, it's very cold is what I'm understanding.
Rob Walling: Yep, we are indoors and we are wearing heavy coats when we go out.
Sherry Walling: When we can breathe. It's so cold you can't really breathe.
Rob Walling: It does hurt your nose hairs sometimes, yeah.
Brian Clark: And the Vikings really didn't help you feel better about it.
Rob Walling: Oh, that is such a bummer.
Sherry Walling: This is a heartbroken city right now.
Rob Walling: We’ve only lived here 18 months, but you really kind of find the hometown love. We really got behind the Vikings this year, they were doing so well.
Brian Clark: Especially after the ending of that Saints game. You even trademarked, yeah, was it “Minnesota Miracle?” And then that didn't work out. Oh, well. I was going for the Vikings, I'll have to say. I'm going for anyone other than the Patriots. So I guess I'm an Eagles fan now, which is kind of difficult.
Rob Walling: Yes, indeed.
Sherry Walling: The Super Bowl is happening like three miles from our house.
Brian Clark: I think what makes it more painful for Minnesotans is, “Yeah, we still have to host the thing. We're just not going to be in it.”
Sherry Walling: We’re trying not to care.
Brian Clark: All right, Sherry, you have been on the show before and that was one of my, I think, favorite episodes in terms of just really drilling down into the real life of entrepreneurism. We talked about some things that some people might think of as a downer, but it's real talk about the dark side of entrepreneurism as opposed to the rah-rah and all the kind of stuff that we have been exposed to in media over the years. Some of our cheerleading super gurus don't really talk about the downside.
You guys are coauthors of a new book, The Entrepreneur's Guide to Keeping Your Sh*t Together, which is following a noticeable trend of late in which book titles have curse words in them. Was that a conscious decision or was it just the most fitting title that came to you?
Sherry Walling: I don't know if this is a great story to tell, but the title was actually suggested by our 11-year-old son. So we thought it was very catchy and cool and we immediately were concerned about where he might have heard such terrible language. But, yeah, he named it. He found the title.
Brian Clark: Yeah. It's amazing what our kids know. I recently had reason to inspect my son's Instagram DMs and I was shocked at my innocent young child’s language. I was like, “Wait, where did you hear these words?” “I heard it from you, Dad.” I remember those old “Don't Do Drugs” commercials.
Anyway, I like it. I think it's appropriate, again, because there is and continues to be other aspects of this crazy life that we lead. And of course, we're going to hear from both of you, and I'm really interested in hearing Rob’s perspective as an entrepreneur.
For those of you who don't know, Rob is the cofounder of Drip, which was acquired by Leadpages and is my email provider of choice. I really enjoy it. As I mentioned, Rob, thanks for making that and continuing to make it better.
How Understanding Who You Are Is Important in Order to Become the Entrepreneur You Need to Be
Brian Clark: But I really want to talk about some of the aspects of the book, because you do cover some of the stuff we talked about last time, Sherry. I want to get into more of where you begin, because I think it's so important and it doesn't get a lot of coverage. And that is really understanding who you are in order to become the entrepreneur that you need to be.
We hear over and over: “This is what you’ve got to do. These are the habits you need to develop. This is who you need to become.” And yet, it's almost as if you're supposed to operate in a vacuum, like you don't already exist and you're going to transform yourself into some magical entity. That just doesn't happen. So, set the stage a little bit for that aspect of it.
Sherry Walling: I think you're right in that there's a lot of pressure and a lot of people selling all of us on this idea that we'll be successful if and when we become this other person or this other version. And I think that plies or plays with a lot of our innate insecurity that who we are isn't good enough and it's not the right time yet, and we don't have what we need in order to be successful as an entrepreneur. Which is of course a great marketing strategy, but really not true.
So what we've tried to do with this book is really help people get in touch with what their natural strengths are, and help them kind of learn to reflect on those and learn to use those better toward the success of their business.
What Is Your Background and What Was Your Journey to Becoming an Entrepreneur?
Brian Clark: Yeah. One thing I try to always do on this show is start with the journey. Not lead with your success, but lead with where you started, because invariably that's where the magic story comes from. Usually, “I failed seven times and then…” That's the most interesting part of it to me. It's in the development and the journey.
So, Sherry, again, you've been on the show before, but let's remind people a little bit about your background and then I'd like to hear the same from Rob.
Sherry Walling: Yeah. I'm a clinical psychologist with a lot of training and background specifically in trauma and anxiety related disorders. I spent the first iteration of my career as an academic, and then also working with military populations largely in VA hospitals, folks who were returning from combat and trying to make the readjustment back to civilian life.
About three years ago, Rob and I started a podcast called Zen Founder, where we wanted to talk about the mental health aspects of entrepreneurship. Both from the psychological side and the relationship side, because we felt like, as you're pointing out, there's a lot of conversation about what you need to be and pressure and not a lot of conversation about how to be healthy and well and happy and still be successful.
I, in the last couple of years, have started making that more and more kind of the center of my career with the podcast Zen Founder, and then doing some consulting with founders and executives around their own mental well-being, and how to create healthy communities that don't burn people out, but help people be as awesome as they can be at the work that they're doing.
Brian Clark: Cool. Rob, how about you?
Rob Walling: Yeah, I'm a software developer by training. I haven't written production code in a few years, because my cofounder revoked my right access to the GitHub Repo — I'm kind of only kidding. I did use to push really crappy code. So I realized at a certain point that I was just a better entrepreneur, perhaps more valuable as a founder than actually hacking away building software.
So I started launching my own products. I was doing consulting for a while and really didn't enjoy the fact that I didn't own things. I mean, talk about unemployable. Sherry said before we started recording, “You're one of the most unemployable people I know,” because I don't enjoy not having the ownership and not having the say. And so I've launched several small software products and then kind of parlayed those up into a number of different apps.
One was called HitTail. It's a SaaS, software as a service application, SEO keyword tool. And then Drip most recently, as you said, which is marketing automation. I also cohost Zen Founder with Sherry. I have Startups For the Rest of Us, which I think it’s the most popular podcast about bootstrapping software startups. And I also run MicroConf as well, which is a conference along the same lines.
Brian Clark: Excellent. Like many people though, of course, you start off doing some form of client work and like you, I was even dissatisfied with that. Because it still felt like instead of one boss, now I had however many I could find. A lot of our listeners are in that boat. Some are happy freelancing, consulting and others want to someday move on.
How Do You Define an “Entrepreneur?”
Brian Clark: That kind of prefaces something I wanted to start with. In chapter two of your book, you talk about what makes an entrepreneur an entrepreneur. This can be a contentious question, because there are some people who consider anyone who breaks free from the traditional employment situation to be somewhat entrepreneurial. There are others who’re like, “No, you're not an entrepreneur, if you, for example, are a freelancer or you buy a franchise or you just run a traditional small business.”
Give me your thoughts on that. And then also, let's kind of dive in on how you mean that within the context of the book.
Rob Walling: One thing that we say in the introduction of the book, it's like who the book is for, because it's called The Entrepreneur's Guide to Keeping Your Sh*t Together. We felt like we wanted to define what that was, and we actually take a pretty broad view of it. Because I view this type of conversation around the stresses and the burdens that the entrepreneurs feel that are different than someone who's working at a salary job. That's the differentiation I think that I tend to make in my own head.
I think that when I was consulting and running a very small one or two person consulting shop, I was an entrepreneur, but I wasn't where I wanted to be, if that makes sense. I wanted to be the next level up in my mind, which was having products and having things that generate revenue without me basically trading dollars for hours.
Brian Clark: Yeah, I agree with you, Rob. I do have a more expansive notion, because it is an incremental journey, and you've got to start somewhere, but that leap is big. I also like the fact that you pointed out it can be stressful right from the beginning regardless of your business model.
Sherry, what are you thinking?
Sherry Walling: Yeah, I think I also have a pretty broad understanding of what it means to be an entrepreneur. I think it has for me a little bit more to do with the assumption of responsibility for one's own livelihood. So the sense in which you're signing up to sign your own paycheck, so to speak. When you take on that kind of responsibility for your own existence, for your family's existence, that's when you cross over into the entrepreneurial world.
Brian Clark: Absolutely. Does that tie in with what you're talking about in the book really? It's that level of responsibility for your own ability to make it in the world economically?
Sherry Walling: I think it does. I also think that that creates this bond between yourself, your identity, your sense of yourself as a person, and the way that you make your living. So, it's a little bit more intertwined — your identity as an entrepreneur and the way that you make your living. They're almost inseparable for many of us, which I think has some unique psychological challenges. It's a little different than like, “I go work at this place, I do this job. They pay my salary.”
What Do You Mean by “Entrepreneurial Shadow?”
Brian Clark: Yeah, absolutely. You also touch on the topic of entrepreneurial types and you touch on strengths and shadows. Is it shadow in the Jungian sense? My Bachelor of Science in psychology is on the wall, so I have to prove that I actually got that thing.
Sherry Walling: I do use that term in the Jungian sense, in the way of thinking about the shadow side of something which is, I mean, Jung had this really fascinating relationship with this idea of shadow. That was the darkness, but it's also where a lot of our creativity comes from — our angst, our passion live in the shadowy bits. The pieces we don't fully have cognitive access to, and the pieces that sometimes we’re pretty motivated to keep at a distance or to keep suppressed.
Brian Clark: Yeah, and we may have touched on that in our last conversation. But it's been a recurring theme on this show that our dysfunctions as entrepreneurs are often our greatest strengths, because we tend to compensate for them one way or another.
Rob, do you have any insight from your own experience that may lend credence to that?
Rob Walling: Oh man, yeah, loads. When I was growing up or as I started to go into the workforce, even working eight hour days when I was younger was hard for me because I'm a momentum player. Especially when I'm writing code — I can't do it as much anymore, but I used to do 12-hour stints, 15-hour stints, and then I'd want to take a day off. And that was definitely a weakness if you want to conform to a work schedule where you have to be there nine to five.
Soon as I realized that it was kind of a superpower and that I could binge and basically get two, three days of work done in essentially a 16-hour straight session, that was like a fantastic realization for me once I was on my own.
The Importance of Self-Knonwledge
Brian Clark: The part of the book that jumped right out at me was your focus of an entire chapter on self-knowledge. Because again, I don't think it's talked enough about. But over the last 20 years, it's been the most important thing to take into account for the next step. And whenever I get off track, it's usually that I'm not abiding that way.
Rob, this may sound familiar to you. Once you get going, you're out there on your own and you start to understand how things work outside the confines of showing up someplace, so that they can write you a check every two weeks, you start seeing opportunity everywhere.
That was my case about two or three years into it, back coming out of the ‘90s. I was just like, everywhere I looked, I saw opportunity, business model, revenue. And then I would play out in my head, I would formulate the entire business plan basically. Then I'd get to the end and go, “Yeah, but I don't want to do that.” And that's the most important part.
Now I don't run through the entire process, because I know I'm not going to do that. Even when you do something you love as an entrepreneur, it's hard. And if you're going to stick with it, you’ve got to be into it. At least me. I think there are some people who are better money-motivated, if you will, who that's all that's there, but I can't do that, not very well. And I don't think that's conducive to mental health as an entrepreneur.
So I'd love to hear both of your thoughts on that topic.
Rob Walling: Yeah. I think especially for me in the early days, I mean, I grew up very working class, solidly working class and had to kind of scratch and claw my way out of salaried employment. I was scared to become a consultant, because I didn't get the paycheck every week.
When I was starting to dip my toe into products, I did whatever it took to make money in terms of even doing things that I wasn't interested in. When I say, “Whatever it took,” I was always ethical and moral and all that, lived up to my values. But it was more like I owned a beach towel ecommerce website, the dropship beach towels, which I don't really have any interest in, but I was trying to get to a number that I could support myself and quit consulting.
I owned an ebook. There was an ebook about bonsai trees that I acquired from the previous owner, and I knew how to market it. So I turned that into 500 or 1,000 a month. It was just this hodgepodge of things.
But to your point, once I got to where I wasn't just scratching and clawing, trying to achieve my freedom, which had been a goal for decades, then I became extremely picky about what I was going to do. Everything from then on was things like MicroConf, which is a passion of mine, Startups For the Rest of Us. I wrote a book on the topic. HitTail was an SEO when I was bigtime in SEO at the time. Drip was email marketing, which is something I've done for…
Suddenly, I had a little bit of breathing room. And once I had that, I could just hit it. I will say, I've enjoyed these years when I really am more picky about what I go after.
Brian Clark: Yeah, I can relate to that as well. I grew up blue color. Well, first person in my family to go to college, put myself through law school. And then found out I hated not only practicing law, but working for anyone whatsoever. And that's scary as hell.
But yeah, I started two real estate companies not because I had any particular passion for real estate. Two things: I understood online marketing. This is back in 2001 when not everyone did, and you could make a lot of money. And I did. I worked way too much, but I needed that phase. I needed the money. I started the company right when my daughter was born. That's a great motivator. But I needed it psychologically. I had to prove that I could build a business that wasn't based on law at all.
I think a lot of people go through the phase where you just have to number one, generate revenue and number two, prove something to yourself before you get the follow-your-passion type phase.
Does Chasing a Goal that Does Not Correlate with Who You Are Lead to Burnout?
Brian Clark: To the psychological aspect of it though, Sherry, do you think continually chasing either money and/or just the naked ambition to succeed without regard for how well it correlates with yourself, do you think that leads to burnout? Causes some of the more psychologically distressing aspects of entrepreneurism?
Sherry Walling: I do. And I think the burnout literature is pretty clear that we can't continue to do something over and over that we don't find meaningful. I just think that we're not that well-equipped to continue to do something, especially if we really don't like it.
I think there's certainly a case to be made for doing something meaningful with the money you make, and seeing that as a means to an end, that then you can make a satisfying life. But I think that certainly we spend so much of our time doing our work, a huge chunk of our lives. And if we aren't able to find some activity to fill our days that we find meaningful in and of itself, then I think that's a recipe for bad mental health outcomes.
Brian Clark: Yeah, I mean it seems that way. Again, maybe I lack the mental toughness to just power through something I don't like doing. But it just doesn't sound like a great way to live, period.
Understanding Personality Fundamentals
Brian Clark: You guys talk about the importance of understanding your personality fundamentals, one of which is introversion versus extroversion. I'm an introvert. A lot of people that were drawn to the Internet are introverts, and yet this stereotypical entrepreneur is more like Gary V – very out there, very extroverted. Rob, I'm guessing introvert, but I don't know.
Rob Walling: Yeah, I was more extroverted when I was younger, but I've definitely, especially over the years, I've flipped to the “I”.
Brian Clark: Did you see that as a benefit or an obstacle? Because I can see it both ways. Yet again, the Internet allows you to do a lot of stuff that makes other people lonely. And for us, we're like, “Woo-hoo! No people.”
Rob Walling: Yeah, that's exactly right. That's the thing, as I came to terms with it, I viewed it as a strength — that I was able to focus and be alone for extended periods of time to create, to write and to write code and think about things. Early on, I viewed it as a weakness.
But I realized that the Internet made it possible for me. It's really nice that I grew up in this time, that we live in this time. I think 50 years ago starting a business, you probably did have to be more of the Ray Kroc or the Gary Vaynerchuk. So I think knowing that about myself specifically also helped me start businesses and launch products that could be done without the big sales personality and needing to talk to people all the time.
Instead of going and starting like an enterprise SaaS company, which you can grow really big really quickly, but you tend to need the CEO as the face of the sales, I wrote a book and I built smaller software products that I could sell online and they were self-serve. That was an adaptive thing.
But it comes back to knowing yourself and realizing like, “I could build a big company doing the enterprise stuff, but I'm really going to hate it. I'm either going to burn myself out or not enjoy it.” And I think that's part of the power of really knowing who you are.
Brian Clark: That's nice to hear that, because I've always avoided the enterprise level. Because number one, my heart is kind of with the little guys. And number two, there was no way that I was going to do what it took to get there.
Going back to the real estate example that I mentioned earlier, the traditional advice for marketing is: you’ve got to knock on doors and you've got to cold call and you’ve got to annoy your neighbors and all of that. And I'm like, “There is no way in hell I'm doing that.” But I also had the insight that people buying houses were turning to the Internet, and if I showed up, then I get the business. So to me, I was like, “This is like shooting fish in a barrel and I don't leave the house.”
Again, it's flipping not only a perceived liability that there's no way I could be that extroverted person and flipping it into a positive, but only because you recognize an opportunity that fits.
Is that it, Sherry, in your estimation? I mean, do introverts sometimes just say, “I can't do that?” Or on the flip side, do extroverts overestimate their ability to succeed as an entrepreneur given that they tend to act more than they think? I don't mean to be rude to our extroverted friends. But the man of action, the woman of action is the extrovert. But in my experience, thinking things through is the greatest superpower we have.
Sherry Walling: Absolutely. And it's not such that an extrovert isn't thoughtful and an introvert can’t communicate. It's that when you really sit down to be reflective about what your core strengths are, you are putting those strengths front and foremost in your business. Those are the things that you are really heavily relying on.
So Rob knows that as an introvert, he can sit at home and code for 16 hours and make something, because he's not starving for human interaction. It makes sense for him to build something that he can totally control on his own, because it capitalizes on his strengths.
The conversation about self-knowledge isn't to say, “I'm not good at this, I can't do that,” because all of these skills can be learned. Communication style can be practiced. Your ability to pitch to a group of people, if you have to do that, you can do that as an introvert. Nothing is off the table. It's just making sure that you're really relying on the cornerstone of your strength and not trying to build a business around someone that you aren't.
The Difference Between Fixed and Growth Mindsets
Brian Clark: Yeah, I agree 100%. You also touch on fixed mindset versus growth mindset. That is a fascinating topic to me, especially over at my other project Further, which is all about personal growth. I guess my first question is, do people with a fixed mindset even try to become entrepreneurs?
Sherry Walling: I think all kinds of people try to become entrepreneurs. I think sometimes with the fixed mindset folks, they’re even really determined to become entrepreneurs. But the process maybe isn't in so much becoming an entrepreneur, it's that, “I am an entrepreneur. I have this set of skills, I went to this business school or I did this and this is what will make me successful.”
But the problem, of course, with a fixed mindset is when you encounter any challenges that you aren't already equipped for, you don't have a mechanism to grow around them or to begin to expand your repertoire of skills in order to deal with a challenge that you didn't foresee.
I think all kinds of folks try it, but whether you can adapt and adjust and learn and grow on the fly is sort of the essential question of the fixed versus growth mindset.
Brian Clark: Yeah. And I guess that's why I asked the question, if people are confused out there. You're right. So you don't realize that you are going to evolve by necessity quickly in your ability to learn, to adapt, to make mistakes and be okay with it. Everything that I've studied about fixed versus growth mindset is that the fixed mindset has a real problem with that, because that mindset inherently believes that you are what you are and that's it. I guess the flipside of that is you can develop a growth mindset if you change your view and think that you can grow.
How Can You Change Your Fixed Mindset?
Brian Clark: I've encountered this before in certain people and it’s amazing. I mean, they really are stuck. How do you suggest people can get past that? Or I think, how do you recognize that you do have this fixed mindset and that it needs to change?
Sherry Walling: I think one of the tells is your capacity to cope with failure. I think fixed mindset folks, if they have early success as entrepreneurs, they're kind of set up in a bad way, because they don't learn this capacity to bounce back or to work around or grow from any early failure.
If you're really successful early on, you might get yourself into an entrepreneurial life without learning these basic skills of, “How do I grow and bounce back when I've had a setback?”
I think asking yourself some really simple questions can help you develop into more of this growth mindset. Questions like, “What do I need to learn in order to be successful at this next level? Or I'm having trouble with this part of my marketing campaign, what are my knowledge gaps? What are my skill gaps? What expertise do I need?” You're basically asking yourself questions about how to make this possible.
The growth mindset is all about believing in what's possible with the right amount of effort and energy and training and practice, instead of the dead end of, “I failed, therefore, I have to hang up my shingle and go live in my basement.”
When Have You Experienced Failure?
Brian Clark: So, Rob, you started small and incrementally did new things, as you talked about, how you did whatever it took to increase your revenue and get to the point you wanted to be. It seems like you had a lot of small successes on the way to a large success with Drip, obviously. Tell us some good failure stories. They're my favorite.
Rob Walling: Oh, boy. Yeah, I mean, I failed in 2014. There was a good one where I almost ran out of cash, mismanaged the business. Drip was growing, just starting to grow quickly. But I had this little bucket of cash in the bank. Frankly, it was more money than I had ever seen in one place. It was about $100,000, and I had built it up over several years of these small businesses. And I hired a head of revenue, which is something I've never done as a bootstrapper. So I mismanaged my cash. It just wasn't something I had a ton of experience with.
Taxes came due, I forgot, “Oh, I underestimated last year and there were some expenses that I hadn't counted on with MicroConf that came late.” Suddenly, I was almost out of money and I was freaking out, so I failed in a couple of respects.
One, I made a mistake with the cash management, and that will never happen again. But the other thing I did is I took it too much upon myself, like I stressed about it on and off for six months. I was doing things to try to fix it, but I let it kind of ruin that part of my life. There were months I regret.
These are the times I've regretted when I look back. Everything I've done as an entrepreneur, I think, “Man, it got me to where I am.” But there are certain snippets of it where I wished I had been more resilient, and I wished I had let the failure impact me less.
Brian Clark: Yeah, isn't that something?
That's another thing that people don't realize. The failure within the context of success. Drip is succeeding wildly and yet you made a mistake underneath the currents that people aren't seeing. It can almost be worse, because you still have to keep up appearances to the outside world while you're under this pressure and beating yourself up over something.
I don't know anyone who hasn't screwed up cash flow like that before. I have, also the tax thing. Yeah, we could do a whole episode on screwing up your estimated taxes.
Rob Walling: Oh man, it was brutal.
Top Tips in Knowing Yourself
Brian Clark: All right, so the theme of this episode I guess is the ancient “Know thyself.” You close out that chapter on self-knowledge with the section called “Know thyself fully or mostly.” Give us your top tips. I'd like to hear hopefully from both of you on how you make that happen. Because again, I think that's the foundation by which not only your economic health emanates from, but also your psychological health.
Sherry Walling: I think you have to create some space in your life for some self-reflection. Whether that's going off on a retreat a couple of times a year, whether that's having some even very simple journaling practice, whether it's tracking your mood, whether it's seeing a therapist, whether it's having a coach — someplace where you do some version of a deep dive into, “How am I doing? What am I learning? What are my strengths right now? What are my weaknesses? What are my anxieties?” And really paying attention to what's going on in your inner life, so that you can first, sort of meet problems before they become really big problems and do something about lingering anxieties. Do something about relationship problems that are becoming patterns.
I think the other side of that is that you can really also pay attention to what you're enjoying and how you're growing and the things that are most satisfying about your life and make sure that you're leaning into those parts of your life too.
Brian Clark: Rob, what do you think?
Rob Walling: Yeah, for me, since I tend to be more of a left brain engineer, I do enjoy the reflection and Sherry has been a good influence on me to take retreats and to sit and think about, “What do you really want? What did you like last year? What did you hate about last year? How can you do more of what you love?” I like that part.
Something else that has helped me over the years are these things that I viewed maybe with a little bit of an eye roll early on, but it's the personality tests. StrengthsFinder was a game changer for me personally (not for everybody). But if you buy the book for 10 bucks, you get a free test. It's 20 minutes of your life and it will tell you some things about yourself. “Hey, you're a learner. Hey, you're a maximizer.” These are some of my strengths.
Once that was kind of put into context, I was like, “Yeah, that is who I am, that is what I like to do.” There's the Enneagram, there's the Kolbe test. I haven't taken Kolbe, but I'm looking forward to it. I love just being told by one of these tests after answering the questions, things about myself that I probably knew subconsciously, but it wasn't fully conscious. And that has helped me realize why I react to certain situations and stimuli the way I do.
Sherry Walling: Hey, honey, I'll tell you all the things all about yourself anytime for free.
Rob Walling: That's great.
Brian Clark: I love it. I'm going to have to end on that. That was too perfect.
The book is called “The Entrepreneur's Guide to Keeping Your Sh*t Together”. If you're looking for some insight that goes beyond the surface level, hustle and grind stuff you hear every day, I would suggest picking this up.
Sherry and Rob, thank you so much for the time and thanks for the work you do.
Sherry Walling: Thanks, Brian, always a pleasure to talk to you.
Brian Clark: All right, everyone. As always, thanks for tuning in and keep going.