Episode 91: Moving from business owner to employee – with Kyle Maurer

Kyle Maurer talks through his journey from being the owner of a marketing agency to working as an employee and the difference between doing what you know and doing what you love.

Today’s guest

Kyle Maurer

Website: Kyle Blog

LinkedIn: Kyle Maurer

Twitter: @MrKyleMaurer

Facebook: Kyle J Maurer

Kyle is an ambitious creator who lives to bridge gaps and bring people together.  He used to be an entrepreneur, but in 2017 he walked away from the marketing agency he had co-founded five years prior.  Since then he’s been working for Sandhills Development, a software company that is primarily focused on WordPress plugins, as the Director of Operations.

Kyle’s background includes lots of web development, marketing, management, teaching, public speaking, consulting, event organizing, podcasting, and product management.

He is also a father of three, a Toastmaster club president, a musician in a band, a craft beer lover, and a travel enthusiast.

What you’ll learn in this episode

  • [02:57] Kyle explains how he came to start his own business.
  • [04:57] Kyle reflects on his attitude when he started his marketing agency.
  • [07:13] Kyle discusses how he felt before making the decision to leave the agency.
  • [13:00] Kyle talks about how he figured out the next step in his career.
  • [14:00] The importance of investing in relationships.
  • [19:31] Kyle explains his emotions during the transition period between leaving the agency and his new role.
  • [21:01] Adjusting and dealing with feelings of being unemployable after working for yourself.
  • [24:10] How Kyle and his employer worked through the challenge of him not being in the right role.
  • [27:07] Utilising your natural talents over acquired talents.
  • [30:02] Kyle explains what he finds the most difficult part of his current role.
  • [32:23] Kyle thinks about where he might be in five years’ time.
  • [35:09] How owning your own company doesn’t necessarily mean you’ll feel fulfilled.
  • [36:20] Exploring your priorities to understand where your best fit could be.

Resources mentioned in this episode

Please note that some of these are affiliate links and we may get a small commission in the event that you make a purchase.  This helps us to cover our expenses and is at no additional cost to you.

To see the resources recommended by all our guests, visit the Resources page.

Episode 91: Moving from business owner to employee - with Kyle Maurer

Jeremy Cline 0:00
Are you being paid to do what you know or to do what you love? Do you use your natural talents in your working life? Or is it talents that you've acquired as a result of the job that you've been in? And does acquiring knowledge and skills inevitably mean that you have to use that knowledge and skills as you go throughout your career? Those are some of the things that we discuss in this week's episode. I'm Jeremy Cline, and this is Change Work Life.

Jeremy Cline 0:38
Hello, and welcome to Change Work Life, the show that's all about beating the Sunday evening blues and enjoying Mondays again. We've spoken quite a lot in the past to people who gave up being an employee to start their own business. But what about doing things the other way around? What happens if you have your own business but decide, actually, it's not for you, and you'd be happier working for someone else? My guest this week is Kyle Maurer and Kyle did just that. Kyle, welcome to the podcast.

Kyle Maurer 1:04
Thank you, Jeremy. It's a privilege to be here.

Jeremy Cline 1:06
Before we go back into your story about this particular change, can you first set the scene for what you're doing now? What's your current role and position?

Kyle Maurer 1:13
Absolutely. I'm the Director of Operations for small software company called Sandhills Development. We're a distributed team, we work from our homes all across the world, small team right now, a few dozen people, and I am in charge of, as I said, operations, making sure that everything internally is running well, I'm responsible for the people, making sure that everyone enjoys their work, finds it fulfilling, is productive every day, and basically, at the end of the day, chooses to come back to work every day. And that entails everything from HR, to culture, to diversity, hiring, recruiting, meetings, and so on. And it's a very rewarding pursuit, something that I enjoy doing quite a bit.

Jeremy Cline 1:53
It sounds quite wide-ranging. I mean, where do you draw the line between overseeing the work and doing the work? I'm thinking, you know, HR, a lot of people, sorry, a lot of companies have their own HR operations. So, I mean, do you actually get hands-on in all that stuff as well, or is it more of an oversight role?

Kyle Maurer 2:09
This is much more oversight, and operations, to be fair, does actually vary. I've talked a lot with other peers in the profession and there are a lot of other operations professionals maybe with the same title and job description as me, but a very different focus internally, maybe a lot more on the production of the work. But in my case, that is generally handled by other department leaders. And I am thinking mostly about the company as a whole, and crafting maybe policies that work for the whole company, working on our career progression framework, opportunities for advancement for everybody in the whole company, and working on communication and collaboration between departments, but essentially thinking about the entire company holistically.

Jeremy Cline 2:49
Let's dive back a bit into your backstory. Can you tell us a little bit about what led up to you starting your own business?

Kyle Maurer 2:57
Absolutely. When I was in my early 20s, I was working in my first full-time position at a niche marketing agency. That was when I learned the basics of all things marketing, from SEO to PPC and content strategies and web design and email and affiliate marketing and PR and all of that. Some of those newly developed skills caught the attention of people in my personal network. And I found myself building websites for more than a few acquaintances in my spare time. And some key events, like getting a promotion and earning employee of the month and leading some successful initiatives and earning high praise from company owners boosted my ego, I think, this is retrospect, of course, but it boosted my ego to an unhealthy degree. And looking back, I was altogether full of unearned confidence. And all that unearned confidence led me to the conclusion that I could just do all of this myself. I thought that I could do all of this by myself, and I wasn't way off. It's not so much that I couldn't do it. It's more that it was really the wrong path for me in the end. I was a little naive, I thought that I had been working in a poorly run agency for a year, and I knew everything there was to know, of course. I was in my early 20s. I also was doing what I knew. And so, when I left that company, I started a marketing agency, because those were the skills that I had developed. And this, I think, is an important point. So many of us proceed deep into our careers just doing what we do for no other reason than because it is what we know. We feel obligated to continue on whichever path we stumbled ourselves onto when we were young. But I think that we shouldn't, now, years later, I've learned this. We shouldn't any more than we should feel obligated to wear green sweaters because our mother dressed us in them often when we were young. We do have the liberty to choose our path. And it took me too many years to figure that out.

Jeremy Cline 4:41
What were you thinking when you started the business? I mean, did you at that stage, were you just diving in thinking, 'Hey, I'm gonna see how this goes', or were you thinking a bit longer term than that in terms of what you might build it to and maybe even how you might exit from it?

Kyle Maurer 4:57
You know, if I started a business today, I would have an attitude like that with less expectations, I think. That is a much wiser approach, a more mature approach, to say something like, 'I'll see how this goes, maybe I can make this work, let's give it a shot. If it doesn't work, that's fine. And I'll pursue something else'. That was not the attitude that I had at the time. I went all in, created a brand with a business partner. And I was completely consumed by this venture, and the identity that I had became the identity of that brand. And they were so tightly coupled that the thought of ever doing something else was a painful idea. So, I approached it with this attitude of having to make it work, because anything else would be a failure.

Jeremy Cline 5:45
How long did you have the business for and how did it change over that time?

Kyle Maurer 5:49
When I first started that marketing agency, it was exciting and rewarding. And it did seem like the possibilities were endless. And we were on track for incredible success. But it was really only a year or two before I started to struggle. I didn't actually like doing it, though I wouldn't allow myself to accept that fact. I felt married to the company I'd created and I felt like that was my identity. I felt like doing anything else would be admitting defeat forever and feeling like a failure. But I ended up working at that agency for five years in total. Now, in that time, I did learn how much I hated working with clients and running a services-based business. But I also learned a lot about the industry I was in, and this is ultimately what led me to where I ended up, working for another company. So, the industry I was in mostly centred on WordPress. And I ended up investing a lot of time and energy into that community. I blogged, I attended events, I organised meetup groups, and just kept going until I was organising large events, large conferences and hosting my own podcasts and travelling the country and the world to speak at events, and generally being very involved in the ecosystem. In that process, I developed a reputation and met an enormous number of people. So, when the day finally came when I said, 'I'm done, I don't want to do this anymore', I was very empowered to make a change.

Jeremy Cline 7:05
What was, if you like, the final straw, what do you think finally led you to admitting to yourself that this wasn't working for you, and you weren't enjoying it?

Kyle Maurer 7:14
Yeah. Running your own business can be a roller coaster, and running an agency where it is, we're serving clients, paid large amounts of money, but there are large gaps in between, makes it even more of a roller coaster where there are very high highs and low lows. And after the first, probably in the third year of running this business, I started a pattern of just about every quarter going into some kind of a funk, you might say, and expressing to my partner that I don't know if this is right, I don't know if I can keep doing this, I'm really frustrated, it feels like this isn't working. And my business partner, every single time would talk me off the edge of the cliff and say, 'It's fine, we can see the light at the end of the tunnel, these things are going to work out, we're going to close these contracts, this project is really good, just stick with it'. And I would say okay, you're right. And then, he would be right, to an extent, and months would go by and it would be great. But then, it would happen again. And that happened maybe a dozen times or so, until it was the spring of 2017, I think that it was my wife who really approached me and she was the one who said, 'You're not happy doing this. You're not, you have to be honest with yourself'. And that was the first time that I got really serious about entertaining other options. And it was also the time when I began to appreciate how large and accessible my network had become due to the reputation I built and all of the involvement in this community I had done.

Jeremy Cline 8:43
Before you made the decision to leave the agency, had you looked into ways in which, the ways in which it was making you unhappy and whether there was anything that you could do about that? So, whether it was having someone else do some of the work you were doing, did you explore that kind of possibility?

Kyle Maurer 9:03
I tried a lot, I really did. And it is a good question and a smart question. Because that, I think, is something important, an attitude that is important to have in these kinds of situations. If you're a little bit frustrated with what you are currently doing, you might not necessarily need to make a dramatic change. Maybe you just need to take stock of what it is that you're responsible for and make adjustments and that could be it. And I definitely tried. There were different times over the course of running that agency where I took on various roles and focus. I did sales primarily, four years, I did a lot of our production, I was actually doing the programming for a lot of the complex websites that we were building and doing some product management for things that we had developed on the side. I ran marketing campaigns and did a lot of different things. But at the end of the day, I discovered that I really didn't want to do this kind of work. I didn't want to do services for other businesses, where at the end of the day, I'm trying to help another company accomplish their goals and another entrepreneur achieve their dreams. I was very attracted increasingly with the idea of working in a product company. And the difference that I saw was with a lot of the clients that we had, we would work with one client and work through a process, and then we'd go to the next client and work through the same process. And then we would go to the next client and do kind of the same process again, and I began to really tire of this repeating process. I felt like there's a whole alphabet of different things that we could do. And for every client, we're doing A, and some clients we get to do B, and then there's a rare client where we ever got to do C. And these are like the steps of iteration and going deeper and advancing the same systems. But if I were working in a product company, I could go as deep as I wanted, continue to work on the same thing indefinitely and improve and go much, much deeper and richer, into much richer experiences, and really push the limits of my abilities. That's the difference that I identified.

Jeremy Cline 11:03
What did your exit look like? You mentioned that you had a business partner, did this result in you sort of selling out your share? Did it result in the entire company being sold? Does it still exist? Is your business partner still involved? What's all that look like?

Kyle Maurer 11:18
Yeah, as a matter of fact, the company does still exist and it's doing fine. I might even say better without me. I don't know that others would say the same. But that's what I believe. But the company still exists, my business partner took over the whole brand. And he did buy me out in a sense. I did actually give him full control of the marketing agency. And I sold him our products division. And he bought that from me. We had some software that we had developed over the years that we were selling. And so, he took over full control of both brands that we had, and I walked away completely.

Jeremy Cline 11:53
What was the conversation with him like when you finally made this decision?

Kyle Maurer 11:57
It started like it had started many times before. But when he came to realise that I was serious this time, to be honest, he wasn't very happy. He wanted me to stay. And when you're running a small agency like that, with only a few people and a lot of big projects, someone important leaving is quite a disruption and throws off a lot of the plans that we had laid, and I had been the point person for a lot of our big accounts. And so, it was not an easy transition out. And there were even times after where he reached out to me and expressed how much he wished that I would come back. But that hasn't happened in some years. And now, I think the company is running even better than it was before.

Jeremy Cline 12:36
So, this wasn't a situation where you had kind of reached an agreement, like a shareholders agreements in the past to govern what might happen if one person wanted to leave?

Kyle Maurer 12:45
Oh, we did, we did have some paperwork that outlined more or less the legal specifics, but not in too great detail.

Jeremy Cline 12:53
When you left, did you already have something lined up to go to, and what was that?

Kyle Maurer 13:01
I did, actually. As soon as I finally came to the conclusion that I needed to pursue something else, and what I wanted to do was work at a product company, and what I wanted to also do was work at a company that I admired and with people that I could learn from, which is one of the challenges inherent in being an entrepreneur is, you're up at the top and the opportunities for you to grow are more limited, in fact, where I got good advice from someone that, who said that if you really want to grow, you need to go work someplace where everyone else is smarter than you. So, I looked around for companies like that. I started by making a list of all the companies in our ecosystem, which I thought I would be happy to work for. And that list was at least a dozen or so, they were places I admired, doing work which interested me, with people I thought I could learn from. Also, they were places run by people who knew me well enough to at least give me a shot or open a conversation.

Jeremy Cline 13:54
Was this people who knew you as a result of the blogging and your general sort of appearance in the space, in the WordPress space?

Kyle Maurer 14:01
Absolutely, yes. Especially, like running a show, a show like this, right? For years, for five straight years, I interviewed someone from the community, another professional, another peer, every single week and got to know a lot of the important people in the ecosystem through that process. And then public speaking and conference organising as well.

Jeremy Cline 14:19
You started to identify the companies that you'd be interested in working for and the people that you'd be interested in working for. So, how did you kind of whittle that down and how did that lead to you getting you your job?

Kyle Maurer 14:31
Well, it was actually pretty easy, in fact. I started by reaching out to the first company on my list, and I pinged the owner in Slack and literally told him, 'I want to work for you'. And he said, 'Okay, let's do it'. And here I am, four years later.

Jeremy Cline 14:44
Wow, that sounds like the easiest job interview in history.

Kyle Maurer 14:48
Well, that's how it went.

Jeremy Cline 14:50
But I guess what we're glossing over is the fact that he already knew you because you'd built up this reputation and networking and you'd kind of, your CV, if you like, was your back catalogue.

Kyle Maurer 15:00
Yes, absolutely, you hit it right on the head, I believe that I got this job so easily because I was a well-known person with a strong reputation. I put in a lot of time over the previous five years making a name for myself and ensuring everyone in the ecosystem knew me. I also think the company was in serious need of help with marketing, which was my professional background. And so, was in a good position to be a good fit here, not just someone that was known and liked, but brought the skills that the team needed.

Jeremy Cline 15:26
When you were doing all the podcasting and speaking and networking, were you doing it because you thought it was principally going to be for the benefit of your own agency, or did you have in the back of your mind that it could lead to other opportunities? What was your thinking?

Kyle Maurer 15:42
What a good question, Jeremy. Actually, to be honest, a lot of the time, I was not consciously doing it for some strategic reason. But I got a lot of fulfilment out of those kinds of pursuits in themselves. Now, there's a few things going on here at once. I was able to rationalise my time investment, one because I did think that raising my own notoriety would help in proving the positioning for our business and to help us get customers. And in some cases, it did. Sometimes when, I remember distinct cases where I was the lead organiser for a conference and someone attended that conference and there was a perception that I was someone of stature. And they approached me and brought me in to their business. And it became a big account for us. And there was a time where that person confided in me that they were the point person for their company, that we weren't competing for any bid, our agency, they thought that they were lucky to get to work with us. And that was a perception that they had based on seeing me in positions of authority and with a whole community of other people essentially going to me for questions, which from my position seems like not a very accurate representation of the reality, I was just a volunteer helping out. But there were times where that perception really helped our business. So, I did think it would help our company. I also did think it would help me grow and open doors. I also did enjoy it, it was really fun, and to get to know people and to be able to put myself in a position where other people would come to me to talk and I could have conversations with the people I wanted to without it being awkward or without me having to be the one initiating them all the time. And then the other thing is, the reality, that only looking back, this was the fact, I didn't like my work. I wasn't looking forward to writing the proposals or doing the client work that I had on my plate. And so, I actually spent a lot of time volunteering in the community, writing speeches to give at conferences, podcasting and things, because I enjoyed that so much more than my day job.

Jeremy Cline 17:41
That's interesting, so it was almost like a form of procrastination. I mean, a very sort of productive procrastination. It's not like, you know.

Kyle Maurer 17:48
It really was, it really was. But I did learn valuable lessons from this process about how powerful reputation can be. It isn't easy, but investing in reputation opens doors. It opens doors in your future which you don't yet know you'll want to walk through.

Jeremy Cline 18:03
And that's the key point, isn't it? That you had done all of this networking, all of this building your own reputation and authority, not necessarily knowing what it was going to do for you, but just having a knowledge that it was probably going to do something and so, it was worth having a crack at it, even if you didn't necessarily know what the end result was gonna be.

Kyle Maurer 18:22
Yeah, you got it, it's that funny thing where you kind of don't know where this is gonna go, but you have a feeling that it will be good. And you'll thank yourself later. That was absolutely the fact.

Jeremy Cline 18:32
When you'd had this extremely short job interview, I'd like to work for you, sure, come on, what sort of position did you go into? What were you doing?

Kyle Maurer 18:40
There wasn't an open position. So, the next thing that this person said was, 'Let me go make a position up that would fit'. And she came back hours later or the next day or something and said, 'Okay, we need help with marketing, so we'd like you to kind of run marketing for one of our brands, essentially'. And I said, 'Sure, that sounds great. I'll happily do that'. And we got started a few weeks later, as I transitioned out of the agency.

Jeremy Cline 19:04
How long was that transition? How long before you sort of accepted this job and you quit the agency?

Kyle Maurer 19:11
It was just a matter of weeks. It might have been a full month, I think, between the date that I agreed to start working for this other company and my last day working for my agency.

Jeremy Cline 19:20
And what was it like on your, say your first day, your first couple of weeks? Did you feel like, 'Yes, I'm doing what I should be doing'? Did you feel like a real weight had been taken off you?

Kyle Maurer 19:33
A lot of things at once. You're right, I think yes to both and yes to even more things besides that. There were a lot of emotions that I experienced in that time because, as I said before, my identity had been very wrapped up into the brand that I had developed and decoupling myself from that was painful, and there was still a sense of regret, a sense of failure that I had to fight and resist, and a little bit of sadness that the thing that I had invested in so much turn into what I had hoped. And there was pride, I was still young too, there was a lot of pride in the fact that I didn't have a boss, I worked for myself and I was running this thing and we were doing fine. And I was proud of that fact. And now I did have a boss and reported to someone else. And well, I like my boss, and it's a good company, and he's a great guy, but I still have a boss, and I just get used to that. So, there were some negative emotions. But there were a lot of, a lot more positives, because I got to work closely with people that I admired so much, people I believe are the best in the business. I got to have a steady salary. When I was running my agency, we ran it such that we the owners always get paid last. And there were definitely times where there was not enough coming in or too big of a gap between our contracts for there to be a sufficient pay cheque for myself and my partner. And it was very volatile. And that had put a lot of stress on us and our families. But that went away. Then, suddenly, my wife and I didn't need to talk about money all the time, like we used to. And so, there was a lot less stress. But the truth also is that, my first year with this company, while it was great and I thought, I do want to continue working for this company, the role that I found myself in wasn't actually a perfect fit. And I found myself in the situation, which I think a lot of former entrepreneurs do, that you feel a little unemployable after you've worked for yourself, that you're put into a situation where you're getting a lot of assignments from someone else. It can be frustrating. And I actually struggled, in my first year I did struggle reporting to someone else, our head of marketing was handing all the assignments to me, and she had made the plan, and I did not excel in that setting. And to the credit of my employer, actually, after that first year, we had a conversation about how it wasn't going really well, mostly me handling those specific assignments. And so, instead of parting ways, I was just put into a different role of essentially greater responsibility, instead of reporting to someone and handling the to-dos that they assigned me, I was given full autonomy to be head of marketing for one of our brands, and I made my own assignments. And that was when I blossomed and really began to thrive working for this company. Because I felt like an entrepreneur, again, I felt like I'm the one who chooses what I work on every single day.

Jeremy Cline 22:20
So, from their perspective, what do you think they could see that wasn't going right before you took this director, this broader role?

Kyle Maurer 22:28
Yeah, looking back, I think there were a lot of decisions made that I wished I had been involved in making. Some were made just before I joined the company. And that was that, the ball was already in motion and I was to help execute on a plan that was already made. And there were cases where I thought I knew better and it frustrated me that we were pursuing a plan that I wouldn't have approved or agreed to had I been involved.

Jeremy Cline 22:57
And how did that manifest itself in terms of sort of your interactions with your boss and your peers at the company?

Kyle Maurer 23:04
Sure, yeah, there were times where I think held things up, we had arguments about how to get certain things done or which things were priorities, maybe I would contribute other ideas that I thought we should do. And the response that came back was, 'We're already working on something, we're not going to table the plan that we already agreed to, to act on this new idea you came up with right now. It's too late in the game, file that away for later'. And there were a lot of those kinds of conversations that led to some resentment on my part. There were times where I had a series of responsibilities which I failed to prioritise properly, and I missed the deadlines on a number of occasions too. I had been coming out of years of just working for myself and being accountable only to myself, and then somebody was giving me stuff that I didn't always want to do and saying get it done by this date. And that was a bit of an adjustment, which I wasn't great at.

Jeremy Cline 23:58
I'm sure in a lot of cases, this sort of situation and these sorts of conversations probably would have led to you parting ways with the company. But in your case, it sounds like it actually ended up you being promoted to this oversight role. How did that come about?

Kyle Maurer 24:12
I think there are a number of things, and I just want to give a lot of credit to my employer for identifying what was wrong, and being willing to give me a chance, something different. And my co-workers as well, being willing to, because we had tried some stuff and it hadn't gone really well. And I don't think any of us would have called that first year like a smashing success. But they were the ones who suggested that I just take over full responsibility of something and develop the plan from scratch myself and be accountable to myself, essentially. And I thought that sounded like a great idea. And they were completely right. There were other things going on as well. And this ends up relating more to the final outcome, where I am today, but having run my own business, I was interested in and familiar with a lot of things that had to do with just essentially administrative stuff and operational things. And the owner of the company had a lot of responsibility, and a lot of things that he couldn't handle. And I stepped in and volunteered to take over a few of those things. For example, there were some administrative tasks that I had done and I said, 'How about I just handled that for you?' And there were like team retreats, team meetups, where all of us, this distributed team would get together, maybe once or twice or three times a year and we would do a group meetup. And that's quite a logistical challenge. And I said, 'How about I just plan those for you? It's a lot of work'. And he said, 'Fine'. And so, I ended up taking on more and more of those things as kind of a secondary set of responsibilities. And those went really well. And so, I was contributing a lot of value to the company by taking over some of the founder's responsibilities, some administrative work, which ultimately led to, after the completion of my second year, being offered a position as the director of operations and doing no more marketing work at all.

Jeremy Cline 25:55
And how did you feel about that?

Kyle Maurer 25:56
Yeah, that was a tremendous change. And it was bittersweet for a moment in the sense that I felt like I had invested a lot of years of my career into marketing, and I had learned a lot and accomplished a lot of things and developed skills. And then, I was going to walk away from all of that completely, and not use any of it anymore. I understand the long view, that this is, it felt like a lot of years, but really, in the terms of the length of my career, it was not extremely significant. And it's more important to find the perfect fit, the best fit for you. But for a minute, it was a little bittersweet to be pivoting in that way. But I did understand that taking on this role as director of operations was a real step forward for me in a number of different ways. And then, really the most important at the end of day is that this was putting me in a position to do something every day that I loved. Not just what I knew, but what I loved.

Jeremy Cline 26:48
When you made this transition, did you feel at that stage that everything that you'd been doing in terms of volunteering to organise things, equipped you for this director of operations role? Or was there a bit of imposter syndrome, where you kind of go to your boss and think, 'Hang on, you want me to be director of operations, but I'm a marketing guy, why on earth would you want me to do that?'

Kyle Maurer 27:10
I probably should have felt that a little more than I did. But I've never felt more confident since I started this. And now that I have been doing it, in what I do, I am extremely self-assured and feel like a fantastic fit in this role. And I did very early on when I took this position. I think that, you're right, a lot of the past experience that I had equipped me well for this. I did organise large conferences and was responsible for a lot of different things and delegating to a lot of people and working through a lot of interpersonal conflicts and managing logistics and things of that nature and was familiar with enough business fundamentals and HR concepts to be productive quickly. But what I realised early is that I've been able to, in this position, leverage a lot of my, what I consider to be my natural talents, instead of my acquired talents, which is what I've been doing in the past that I mentioned before, the importance of recognising we have the liberty to pursue what we want and not be married to something just because it's what we happen to know. And I had spent most of the years doing what I happen to know. Now I feel like I'm doing what I'm naturally inclined to do. I want to get up every single day and try and make other people happy and fulfilled and productive. I want to make this a good experience for them. I'm driven to do that. And this is what I've been driven to do ever since I was a child, ever since I was young, the oldest of a large family of kids, I was always a leader who wanted to make sure everybody else was having fun. I was organising events and activities for everyone in our family and amongst all our friends and groups. And I've always had a role as a leader, the person trying to make everyone have a good experience. And now, it feels like I'm just getting to do that again every day.

Jeremy Cline 28:53
Unpacking your natural talents and what you love to do can actually be quite a difficult thing. Did this just come to you naturally, looking back on your previous experiences? Or did you have any help to identify that this was where your natural talents lay?

Kyle Maurer 29:09
I think it was noticed by some people, like the founder of the company did look at the various things that I was responsible for, like I was splitting my time between doing marketing work and doing some administrative and operational tasks, and others of the company saw that I was doing passable work for my marketing responsibilities and excelling at my operational responsibilities, that was going great. And I was doing it better than anybody else felt that they could, if they tried, and enjoying it. And that was definitely noticed by my colleagues, even if I didn't notice myself. And my wife too, talking to her, definitely observed the things, you know, when this opportunity came, she said, 'This is a chance to spend all of your time doing the things you're most enthusiastic about', to her and their credit.

Jeremy Cline 29:55
You're now doing something which leverages your natural talents, which you love doing, there's got to be some downsides. What's the hardest thing about what you do now in operations?

Kyle Maurer 30:05
Yeah, I am definitely in a privileged position, where I get to do what I love every single day, and I get to do it for people that I think very highly of, get to feel, I feel like an entrepreneur, because I still every day do what I want and what I think is important with very little accountability except to myself. And I think it's maybe the entrepreneur in me, the former entrepreneur or something, like that comes from, but there are still very real challenges. And a couple that come to mind, one is, I am of the personality type where I want everyone to be happy, I'm driven for that. And that's, in reality, that's near impossible, especially the larger our team gets, there's no way that I really can satisfy everyone. Constantly, there are conflicting interests and any change that I make is going to improve the situation for some and frustrate others. We have a diverse group of people here, and I'm always trying to reach out to them and ask them what would make their jobs easier, or reduce their stress or make them more fulfilled at work or increase the likelihood of them continuing to work here or anything of that kind, and I get different answers from everyone. So, it's challenging for me to try and find the best solution that can make the most people the most happy. And another challenge is just the fact that I'm very ambitious, and I care a lot. And we're a small company. And some of our products are positioned against huge competitors that are venture-backed, with teams 10 times our size or larger. And it can be frustrating to see how slow our progress seems and feels at times, relative to what's happening outside in the ecosystem. And that's just a challenge that we need to accept, we've chosen to be bootstrapped-only company and not take any funding and grow at our own pace, regardless of what is helping elsewhere, and emphasise our people first and not buy into the hustle culture. We're very much not of the Silicon Valley mindset, which I do actually appreciate and it's great, but sometimes it feels like there's a mountain of work to do, and we're just chipping away at tiny, tiny pieces of it. And that can be hard.

Jeremy Cline 32:16
And where do you see your future? What do you think is going to happen for you, in the sense that anyone can predict anything in the current 12 or 18 months we've had, where do you think you're going to end up in five years' time?

Kyle Maurer 32:26
Yeah, when I was younger, I actually was more inclined to give a lot more direct and specific answers to those questions. But now, I have enough experience to know that, as you said, we can't predict the future. And that's fine. And it can be useful sometimes as an exercise, but I spend very little time thinking about the future I trust in my future self to make good decisions when the time come, and I know that there's going to be better things that come my way, I don't know what they're going to be. But I do believe that I'm at a great company that values people and is on a great trajectory. We're growing, I'm excited about the progress that we're making, and I'm excited about the impact that I am making at this company, the difference that I am getting to make, and so, I could very well still be with this company in five years. And at the rate that we have continued to grow, we could be twice this size five years from now. And I could have a different title. I don't know, I'm Director of Operations right now, maybe Chief Operations Officer or something in my future. And I am still only in my early 30s, I could see myself being a CEO of something at some point someday. I like the exercise of building companies and refining companies and making companies work really well. Thinking about every aspect of a business is a passion of mine, and probably what I will spend the rest of my career doing, building and growing companies.

Jeremy Cline 33:44
So, do you think you will go back to being an entrepreneur? Or is this basically, you will be an entrepreneur just doing it in a very different way to the way that you first did it?

Kyle Maurer 33:55
Yeah, you're probably right in all of it, I think. The truth is that I feel like an entrepreneur right now, even though I am not. I feel like one because I have such complete autonomy. I get to look at the whole company and ask the question, what does this company need? And then I choose what is most important, and then I go and work on that and have complete freedom. And that feels like I have ownership. That was something that, it took me a long time to learn. I used to believe that having like legal ownership over the business was really important. But at the end of the day, what is really important to me is having ownership over what I do. So, I feel like this and I think that this will be satisfying for me for a long time as long as this remains the case, though I do want to continue to grow and go up and manage larger teams and bigger groups and bigger companies. I could see myself absolutely continuing in a position within a company, as long as I continue to have ownership over what I'm doing and that continues to grow larger and larger. There could also very likely be a change in the future, where I start my own company or take over something of someone else's and grow it to the next level. I could definitely see myself in that position in the future.

Jeremy Cline 35:04
So, you said that you feel like an entrepreneur, but without being an entrepreneur. What's the difference between the two states? Is it just ownership?

Kyle Maurer 35:12
This is something that I took a while to realise, but I think it matters that, maybe some advice that I would give other people, that having legal ownership over the company you work for is not a requirement to be fulfilled. No matter how much you hate having a boss maybe, like I thought I did, or require autonomy or resent limits to your growth or relish freedom or think you're unemployable, believe me, a job does exist which you will love. And I've fortunately found a job where I feel like I'm getting all, I feel like I'm having my cake and eating it too. A problem, I think here, Jeremy, is that we're all informed by our own experiences and the problem with that is that, even the most experienced person has such a small set of experience, you could have had hundreds of jobs in your career, and that's still basically insignificant compared to what is actually out there. The analogy that works for me is, I live in a modest little town of about 35,000 people, and we have what most towns have, malls, parks, restaurants, breweries, museums, schools, churches, shops, libraries, all of that. I've seen a lot of what's here, maybe even most. I've eaten at most of the restaurants and walked in most of the parks and shopped in most of the stores. What if I were to tell you that based on my experience exploring my town, I think I'm a pretty well-travelled man? So, me saying that I know what's out there in terms of work opportunities, because I've worked lots of jobs is like me saying I'm well-travelled because I've explored most of one single town in this world. I haven't even come close to scratching the surface of what is out there. Finding work fulfilment starts with understanding priorities. If you prioritise freedom and flexibility, there are companies for which you could work, which allow you to work from anywhere, at any time, with incredible flexibility, like where I work. If you prioritise your own autonomy, there are loads of companies and roles in which you can effectively be your own boss within a larger team. And if you prioritise growth opportunities, there are definitely companies with generous salaries and clear paths for growth and fantastic incentives and equity programmes and more, where the sky's the limit within the organisation. It's a question of whatever priorities you are, but kind of like the point that you raised earlier in the conversation, we can accomplish any of it within a company, just as much as we could without a company and really legal ownership might be the only difference.

Jeremy Cline 37:16
Kyle, this has been absolutely fascinating. As you've gone through your journey, have there been any external resources, books, quotes, anything like that, which have just really helped you and which you can recommend people take a look at?

Kyle Maurer 37:29
There certainly are plenty. There's something that I have tried to advise a lot of other professionals who are looking to pursue their careers, grow their careers, find their place, and that is spend some time on online compensation related services and directories and resources. I spend a lot of time looking at compensation and figuring out how our team needs to be paid. And I think a smart thing for any professional to do is to really thoroughly understand what the market looks like and what the opportunities are for someone with your set of skills or in your set of interests. So, there are a lot of different sites that you can go on to look up what potential salaries and benefits and work environments and job titles and job descriptions exist for someone like yourself. I encourage people to study those. So, you can look at sites like Indeed and Glassdoor and PayScale and Simply Hired and LinkedIn and dozens of others of that kind. I maybe referenced a bunch of them at once, but routinely familiarise yourself with what the market says you should be making, you should know that, you should know those numbers offhand. Familiarise yourself with the benefits the companies are paying, familiarise yourself with the job descriptions that exist for functions like yours, and understand what realistic opportunities exist for you. That is something that I encourage people to study a lot.

Jeremy Cline 38:47
Fantastic. That's a really interesting approach. I've not heard that one before. That's great. Kyle, if people want to get in touch with you, how can they best do that?

Kyle Maurer 38:55
Thanks, Jeremy. If you want to reach out to me, you're welcome to follow me on Twitter @MrKyleMaurer. I have a blog, kyleblog.net, and I spend a lot of my time over on our company website sandhillsdev.com.

Jeremy Cline 39:07
Fantastic. I'll put links to all of those in the show notes. Kyle, really interesting conversation. Thanks so much for joining me today.

Kyle Maurer 39:13
Thank you, Jeremy.

Jeremy Cline 39:14
Okay, hope you enjoyed that interview with Kyle Maurer. I was really glad that I was able to get Kyle as a guest, so that we could explore the perspective of someone who had gone from being an entrepreneur, from owning their own business, to being an employee. And what I learned was that, I think a lot of the things that people crave from having their own business, things like freedom and autonomy and the ability to do pretty much what they want to do, well, you don't necessarily need to be an entrepreneur or be a business owner more specifically, in order to do that. It was apparent to me that Kyle really still is an entrepreneur. He has that freedom. He has that flexibility. He has the ability to mould things the way he wants them to be, but he's found a way to do that as an employee with the security that all that entails. What Kyle was saying about doing what you love versus doing what you know, and leveraging your natural talent rather than your required talent, was something that really chimed with me. In my day job as a lawyer, there is no question that I leverage my knowledge, and I leverage the skills that I've acquired over years of acting as a lawyer. But am I doing what I love? Am I leveraging things which come naturally to me? Well, I think the jury's still out on that one.

Jeremy Cline 39:14
A full transcript of the episode and a summary of everything we've talked about are on the show notes page for this episode, they're at changeworklife.com/91. And if you'd like to explore a bit further where your natural talents might lie, then do check out the exercises on my website, which you'll find at changeworklife.com/happy. That's changeworklive.com/happy, H-A-P-P-Y, there's a couple of exercises there, the first of which really is intended to help you work out what stuff do you actually enjoy doing, what is it that actually comes naturally to you. So, do check out those exercises. As we get closer and closer to Episode 100, we've got some more great interviews to come. So, do make sure you subscribe to the show if you are not already, and I can't wait to see you in next week's episode. Cheers. Bye.

Thank you for listening!

If you have any questions or comments, please fill out the form on the Contact page.

I would be so grateful if you’d: