Defining Success For Yourself

Episode 14

We all start businesses for different reasons, and define success in different ways. As you get older, I’ve found that my view of success changes, and that my priorities shift. Sometimes it’s not all about money, but it becomes more about the freedom to do work you find interesting, or the flexibility to spend time with your family. As we start the new year, I thought it’d be good to ask yourself some questions about how you define success and how that impacts starting and growing your business.

Thanks for listening to this episode of The Stretch Goals Podcast! We'd love to hear your thoughts on this episode and answer any questions.

Find us on Twitter @The_Scott_Davis or @RobDickersonJr


Robert: In this episode, Scott and I are gonna be talking about defining success for yourself, and how that impacts starting and growing your business.

Scott: This is the Stretch Goals podcast where each week we’ll share insights and lessons learned, based on our experiences as entrepreneurs. We’ll challenge you to create ambitious goals as you start and grow your business. I’m your host, Scott Davis.

Robert: I’m Robert Dickerson. We all start businesses for different reasons, and define success in different ways. As you get older, I’ve found that my view of success changes, and that my priorities shift. Sometimes it’s not all about money, but it becomes more about the freedom to do work you find interesting, or the flexibility to spend time with your family. As we start the new year, I thought it’d be good to ask yourself some questions about how you define success and how that impacts starting and growing your business. Scott, happy new year.

Scott: Happy new year, my friend.

Robert: We are in 2017. Our podcast name is Stretch Goals, but we haven’t really addressed that topic of stretch goals and how we define it. I thought we could weave that into this episode, as everyone is thinking about their goals of 2017, and how we’re gonna get started. To start out, let’s talk about what success means to both of us, because I think it changes over time. For me, now it’s not all about the money, but it’s more about finding time to spend with my family, and find a work that’s interesting. I enjoy working with people that have similar goals and similar skills. Have you found out over time that your priorities have shifted in terms of what success means?

Scott: Yeah, absolutely. When I was younger, it was all about chasing the money, chasing the fast cars, chasing the women. Obviously I have all of those things. These days it’s more about I call them passion projects. What I mean by that is if it’s something that I can get behind, and the vision of what’s trying to be achieved, then I’m on board 100%. To me, that’s what makes you want to get out of bed every day, is that passion to go out and build whatever it is you’re trying to build. I look for those types of opportunities.

I also look for is it a good team of people that I want to work with? Money’s nice, and obviously we have bills to pay, and don’t get me wrong, I wanna be paid, but there’s also times where you look at a scenario and go, “Okay, you know what? This is all fun, and it’s gonna be personally fulfilling for me, so I’m gonna go ahead and, you know, maybe do this for equity, or just see what happens.” It’s definitely changed. For me, it’s all about, like you said, family. I wanna spend as much time with family. I want that flexibility. I don’t wanna be in an office 10 hours a day. I wanna have lunch with my family every day and be able to see my son take his first steps.

Robert: A lot of times we’ll possibly give up money to have those things. It changes, and I’ve changed over time as well. I value now, just like you’re saying, picking and choosing the opportunities that you think are interesting. You can’t really start out that way. You kind of have to work your way towards that over time, as you advance in your career and as you build different businesses. For me, I really value that, and like you said, being able to have the flexibility to work wherever and whenever I want to. I’ve begun to value more, like you were saying, the team of people that you work with. I enjoy doing this podcast with you just because we’re friends and it’s nice to talk every week.

Scott: And because I’m usually topless when we’re recording.

Robert: See your beautiful face. You start enjoying to work with different people. There’s other projects that I work on with some other of my friends. I enjoy that, I enjoy being pushed by people that I respect, and enjoy working with them.

Scott: I wanna take a step back. I agree that being able to work with people that you enjoy working with, whether it’s their expertise or just some type of camaraderie, is always beneficial. What I’m about to say is by no means comparing myself to Lebron James, but look at Lebron James. When he went to re-sign, every team in the NBA wanted him to come to their team. Some of them didn’t make an offer because they knew that they couldn’t afford him, or whatever. That’s the same thing that we experience as software engineers. We’ve got recruiters calling all the time. We’ve got opportunities that we can apply for.

I’m not saying we get job offers every day, but what I am saying is that there’s opportunities being a senior engineer. You kinda get to pick and choose. That’s a great position to be in, but like you said, you don’t start off there. It takes a certain amount of credibility, a certain amount of experience, and to a certain extent, at certain levels, even some notoriety. You’ve got a history and people look at that. It’s good to be in that position. Part of being successful, my definition of success, is part of what I just said, the ability to be able to choose those projects that I wanna work on.

Robert: I feel like I haven’t achieved success yet, just because I’m always pushing myself. While I’m closer to where I wanna be, I’m always still working on it. I think you would say that as well, that you’re always kinda pushing and driving, cause that’s just kinda the people that we are. We’re always trying to get better each day and push for that success. One of the things I think you just mentioned is people think they’re kind of owed that success immediately, and they don’t wanna work for it. How do you get there when you’re first starting out? I think a lot of people will think, “Oh, I want that flexibility immediately,” but it just doesn’t happen.

Scott: Success is dynamic. What I mean by that is, at least for me, my definition of success is dynamic. My short-term goal is X, but my long-term goal is something completely different. For me, I think success is just the whole journey. I wanna go from here to whenever I decide to stop, and look back and have no regrets. That’s what it’s about for me. It’s not about a specific app or a specific anything. I’ve sold a business. Was it successful? Sure, but that didn’t define me. That was a moment in my journey that I attribute to a long-term success. The other parts of it is, I forgot what you asked.

Robert: The moment comment is really interesting to me because it’s something I’ve been thinking about a lot, and actually I’ve kinda gone through, is that as you go through life, there’re these moments that are kind of, I guess you would define, success for yourself. You move on from that. You move on to other things. I spend a lot of time thinking about once I reach those moments, whatever they may be, personalized for myself, what do I do after that? What is my next goal? What does success look like beyond that? For the listeners, that could be anything along the way of your career, of your life, getting married, having kids, career goals. All these different things are kinda milestones you set out there. What happens after that? Really thinking about that but also living in the moment to enjoy what you have now.

Scott: You hit it dead on. I remember when I younger, I very much had this idea that I wanted to buy a BMW, and that was gonna be like the crowning achievement of my life. When I bought it, I remember I kinda had this buzzkill. I was like, “Well, now what?” Then I wanted to be a manager of a software team in a Fortune 500 company. I did that, and now what? Then I was a director, and then I started my own business, and then I sold it. You sold a business. Then it’s kinda like, “Oh, this is awesome, but now what?” For a minute it’s kinda like, “Wow, I sold a business. Man, I can do whatever I want.” No, that’s not true. You’re kinda like, “Okay, well now what?” That should be the hashtag of this episode, #NowWhat.

When I retire, I’m gonna be in trouble. I don’t know if I can ever retire because it’s like you said. Our success is a different definition than I think most people. I know this much. Look at the CEO of Twitter, or not the CEO, maybe the CTO. He just quit Twitter to go work for some other company, just in the last day or two, because he wants a different piece of success in his story. I think that’s how everybody is. Donald Trump, he ran for President. Most people would say he’s probably successful financially, but that’s just one piece of the puzzle. We have to look at that like that’s really what that journey that I’m talking about is. It’s multiple pieces. It’s not just what you do for a living, or have you had kids, or whatever. The other thing is don’t let pieces that are missing define the whole journey. If you don’t have kids yet, or you haven’t sold a business yet, it doesn’t mean you’re not successful. You have to look at the whole story.

Robert: I like the way you said that because it’s definitely true. Don’t compare yourself to other people. You could be successful without having big exits from businesses. You could have a lifestyle business that you enjoy doing and that gives you the flexibility to live your life and enjoy time with family. For me, I value that a lot. Is money nice? Sure, but I’ve come to value experiences over physical objects and things. Going on vacation with your family, to me, means a lot more than me going and buying a car or something like that. It’s just kinda your personal traits and what you value.

Scott: What’s interesting about that too is when I was younger, I always would try to find the cheapest vacation possible because it was about the money. I wanted to go on vacation, but I wanted to be stingy about it. To an extent, I still try to save money, but I’m at a point in my life where it’s like if I have to pay an extra $1000 to have an incrementally better time, I’m absolutely gonna do it.

Robert: Yeah cause you can remember those things more than you could remember when you bought that beamer. You’ll probably remember it, but it’ll fade pretty quickly.

Scott: Don’t get me wrong, that beamer was freaking awesome. I had a lot of fun with it.

Robert: It was better than your Neon, that’s for sure.

Scott: Yes, my first car was white Dodge Neon. I blew the head gasket and the engine after two years because I drove it like a BMW.

Robert: When we were younger, that was success for us. You had a car, we could go around.

Scott: You remember in high school, everybody either had a Ford Mustang, a Camaro, some older model BMW, or a pickup truck. Then there was the normal kids, like us. We just had whatever our parents bought us.

Robert: I didn’t even have a car. I was unsuccessful back then. My success predicated on finding someone with a vehicle to carry me around.

Scott: Which ended up being me some of the time.

Robert: Let’s talk about when we named this podcast Stretch Goals, we were kinda thinking about things a lot this similar line. How do we define ambitious goals for ourselves that, while they might seem impossible, it’s something that we work towards everyday to achieve. I like the idea of stretch goals just because goals you might achieve over time, but there’s always kinda that longer-term view of what are you trying to do with your life? What are you trying to do with your business? Just kinda puts a marker out there that you can think about as you work every day.

Scott: What is your stretch goals, Rob?

Robert: I was thinking about that. For me now, it’s about creating products that really improve the quality of people’s live. With Mapout, I’m really focusing on the education space, and using education as a tool to enable people to really do a bunch of different things. Education can allow you to get a better job, it can bring people up to having education that maybe it’ll create opportunities that they don’t have before, kinda reducing the cost of colleges and things like that, and better aligning you with the workforce. I kind of view education as a life-long journey to get where you wanna go. That’s where I’m trying to position Mapout as a tool that enables that learning so that you can continue to get better every day. Learning for me is kind of a life-long endeavor. Every day I’m trying to learn, trying to get better, and enjoy doing that. I’m trying to weave that into my business.

I’ve been also looking at applying education in the healthcare space. How can I help patients? One area I’m looking at is patients with cancers. How can I use education to help them kinda make informed decisions about their treatment options, and kind of enable them to live better through that. Those are kinda my stretch goals for this year, is kinda looking at how I can do that. From a personal perspective, we kinda talked about it, is that I wanna find work that’s challenging and work with people that kinda push me and that I respect. I’m always looking for those opportunities out there as well.

Scott: Those are good goals.

Robert: What about you? What are your stretch goals for this year?

Scott: I don’t make New Year’s resolutions. I just think they’re stupid because I think if it’s important enough to you, you should be doing it anyway. I don’t necessary have goals for the year.

Robert: You’re not going to the gym this year, then?

Scott: No. I would say if I had a resolution it would be to make sure I’m as healthy as possible for my children. That’s an ongoing thing. That’s not like, “Hey, this year only I’m gonna do this.” Obviously you have financial goals, like, “Hey, I wanna save this much money or make this much money this year,” but those aren’t things that I consider to be stretch goals. For me, it’s just continuing to build products that I’m passionate about and getting behind a product that has potential, and getting to be a part of something that maybe I wouldn’t have otherwise been a part of. I’m not afraid to reach out to people and make connections.

Robert: How do you identify those things? How do you identify the project that kinda piques your interest. I know people talk to you all the time and kinda throw ideas your way, and you’re involved in different startups. How do people pique your interest? What kinda gets you excited?

Scott: I think for me it’s what can I relate to? What do I do in my everyday life that is something that’s important to me, or something that could be easier in my life. It’s things that resonate with me personally, that I understand. If I understand it, then I’m ahead of the game, in my mind. It’s like, “Oh, all I need to do I just go build something.” If it’s something I don’t understand, like string theory, I’m gonna have to do a little bit of research before I.

My wife and I, we eat out a lot at dinner. We’ve got kids. Disrupting that dining space to where you can have a more seamless experience while you’re eating, what’s gonna make that better? That’s something that’s attractive to me. Obviously I like sports, so being able to impact the sports industry. Those types of things are things that I’m passionate about. When I look at my stretch goals, I wanna get to a point down the line where I can take a few years off and travel and spend time with the kids, and not have to worry about money. That’s what I wanna do. I wanna take three to five years and do nothing but enjoy life, and then maybe I go back to work after that. The point is I don’t wanna be hustling until the day I drop.

Robert: I thought about that a lot, but then I think about would I really be happy taking three to five years off? Maybe what you’re working on changes, but I still feel like I have that drive to learn new things and dabble in different things.

Scott: Me, too.

Robert: While it’d be nice to go sit on a beach for a while, I don’t think I could that for a long period of time.

Scott: I agree. I will never be away from my computer for even a month at a time. It’s just not gonna happen. I’ll always be dabbling with thing, but what I mean is I don’t wanna be tied to projects.

Robert: You can pick and choose what you wanna work on, when you wanna work on it.

Scott: Yeah, and really what I mean is I just wanna build stuff that I think’s cool, and not even care if it makes money. I just wanna build something because it’s something I’ve always wanted to build. That would be something I find enjoyable. That’s how my retirement’s gonna be. If and when I retire, it’s gonna be like, “Hm, you know, I’m gonna go build this stupid thing I’ve been thinking about for 37 years.”

Robert: That’s the problem, too, about building a business around your passion, is that sometimes it takes some of the fun out of the passion cause your so focused on it every day, about making money and about driving it forward, that you don’t have that time and flexibility to kinda be creative around it.

Scott: Absolutely. I wrote an article in Medium about why I sold my first business. We’ll link it up on the website. That’s basically why. I lost the passion because what I had set out to do that was fun was no longer fun because it became all about the numbers and about the customers. For me that stretch goal isn’t about that. I wanna create experiences that just deliver themselves, like, “Hey, I’ve built a product and you can use it in any number of ways and it’s gonna make your life better.” That’s the kind of stuff I like building.

Robert: It’s kinda cool. I was reading yesterday. I don’t know if you use Zoom for video conferencing. They just raised like $100 million. I started thinking about that. If you had $100 million, even a couple million dollars, what you could do with your business and kinda the flexibility you would have to grow it, it’s kinda mind-boggling when you think about it. He just picked it out of the air, just said, “Uh, how much can I ask for that I’ll never have to ask for money again? 1 million.”

Scott: Money brings opportunity. The more money you have to throw into something, in theory, the easier it is to try and take it to the next level. That’s not always the case, but it makes it easier. What’s gonna be easier, bootstrapping a brand-new startup or having $1 million and starting a startup?

Robert: I constantly think about that because I see people raising money, and they’re able to hire these large teams. Bootstrapping is rough. It’s hard to get over that hump. Then I have the flexibility to kind of make the company how I wanna do it, too, rather than have investors that are kinda telling me where I need to go.

Scott: I’m gonna redefine bootstrapping, by the way. You guys heard it here first. When I have $100 million, I’m gonna take $1000 bills and strap them to my boot. Walk around town. That’s gonna be the new bootstrapping.

Robert: To kinda wrap this episode up, I wanted to talk about how these stretch goals affect your business. How you define different stretch goals both for your self personally, you can also define them for your business. That helps define who your ideal customers are, how you wanna hire and grow your team, and kinda the culture you wanna create. I wanted to talk a little bit about that and how it affects your business. As you’re thinking about 2017, you’re kinda defining the goals that you wanna set for your business, and you define these stretch goals. I’d like to take this kind of as an exercise too for everyone listening. Think about your business and what those stretch goals are, and Tweet them to us. Let us know so that we can help you be accountable for those stretch goals. Then let’s figure out how those goals will affect your business.

I know for me, for Mapout, because I wanna improve the quality of people’s lives, it means that I have to develop a product that is accessible by a lot of people, and it’s easy to use and it’s easy to get educational materials on there. That kinda drives who those customers are, and it drives the teams and what I wanna build, what I wanna create. Just kinda think about that. What are your thoughts about that, Scott, as you think about your goals this year. How is that kind of helping moving your business forward this year?

Scott: First of all I wanna say, reach out to us and let us know what you’re stretch goals are, like Rob hinted at. We wanna have that conversation with you, and maybe have you on the podcast. We wanna hear about what you’re doing, how you got there, and if you achieved it, and all that good stuff. For me it’s mostly about culture and just maintaining passion, and being able to execute on a vision. Like I said, I wanna build apps that are gonna change experiences. I wouldn’t say disruptive because it’s got a little bit of friction to that word. I wanna create technologies that improve the way people live their lives, in various ways. I don’t necessarily mean like giving you a new arm, but I wanna enhance experiences that you may already have. That’s what I wanna focus on this year. That’s really what I’m building and what I’m doing. That’s my stretch goal for my business.

Robert: For me as well it’s kinda like using technology to enable different things. That can mean a lot of different things. I feel like all the businesses and products that I’ve built, the goal at least was to focus on those kind of experiences and making people’s lives better. When I develop things that aren’t kind of in that vein, it’s just like, “Why am I doing this?” It might be a fun side project.

Scott: Rob, you make my life better.

Robert: That’s good. Thanks for listening, everyone. Think about what your stretch goals are, Tweet at us, and let us know. We look forward to hearing from you.

Scott: Give us a like on iTunes, thank you.

Robert: Yes, we appreciate it.

Scott: Thanks for listening to this episode of the Stretch Goals podcast. You can access the show notes for this episode and listen to other episodes by heading over to

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Each week we'll share insights and lessons learned to help you create ambitious goals for your business.

Robert Dickerson


Robert Dickerson is the Founder and CEO of Mapout a mobile learning platform that uses video courses to educate customers and train employees. He helps companies develop and launch their products.

Scott Davis


Scott Davis is the Founder and CEO of MobX, a mobile development software agency. He has 20 years of experience developing software for Government, Finance, Sports and the Telecommunications industry.