What can we learn from micro-pivots, those little hop, skips and cookie crumbs we take and leave on the path as we navigate our career? From VP of Sales in Manufacturing to Workplace Trauma Coach, meet Rob Connelly.
What can we learn from micro-pivots, those little hop, skips and cookie crumbs we take and leave on the path as we navigate our career?
In this episode, we meet Rob Connelly from Charleston, South Carolina, who went from VP of Sales in the manufacturing industry to starting his own business as a workplace trauma coach. Rob’s journey started with helping turn around his cousin’s window and door business, which sparked his love for problem-solving and team development. Over the years, he’s made several micro-pivots, testing out different industries and roles, all while finding the work that truly aligns with his values and passions.
Rob opens up about the power of reflecting on your values, being honest with yourself, and how side jobs and hobbies can help you explore new interests before making a full leap. He’s proof that sometimes, multiple career flips are exactly what you need to grow personally and professionally.
If you're feeling stuck or looking for inspiration to make your next move, Rob's story is full of takeaways on designing a fulfilling work life, especially when it comes to addressing and healing from workplace trauma.
Connect with Rob
LinkedIn: https://www.linkedin.com/in/rob-connelly/
Turnstile Coaching: https://turnstilecoaching.com/professional-coaching/
Rob’s Music: https://robconnellymusic.com/
Jenny Dempsey (00:00.044)
and we spend more time trying to prevent the things that we're afraid of than we do actually building our life the way we want it. Welcome to the Career Flipper, a weekly podcast featuring career change stories from people around the world in a bunch of different industries about how they get from point A to point B and all the twists and turns in between. I'm Jenny Dempsey, your career flipping host. After more than a decade working in customer service and experience leadership at tech startups is
as teaching to Udemy training courses, speaking at business conferences, things like that, I gullied off. And despite my experience, I received hundreds of job rejections. I just couldn't land a new job. And I really started to question my worth. What am I supposed to do now? Then a friend gave me an old junkie table. I saw potential. I binged YouTube, TikTok, and Instagram videos to learn how to fix it up and
found joy in giving something unwanted a brand new chance at life, which really resonated with me after getting laid off and feeling unwanted myself. This led me to start my furniture makeover and restoration business, San Diego Furniture Flipper, where I rescue and restore good furniture to keep it out of the landfill. You can follow along with the makeovers over on Instagram if you want. Alongside the furniture flips, I host the show,
speaking events and yes, still do some small scale customer service consulting on the side. Okay, so even with all these amazing things I've developed over the past couple years, I was still feeling pretty alone and wondering if I was a bit delusional about this new path. I mean, who really goes from the corporate tech world to being covered in paint and sawdust in their garage? So I reached out to a few people on LinkedIn that I knew who'd also put their careers
And hearing their stories motivated me and it made me realize that it's okay to change direction at any point in life. And I soon discovered that there are way more people out there who flipped their careers more than I'd ever imagined. And I thought if their stories are helping me feel less alone and more confident in my career path choices, they might help someone else too. And so that's why I created this podcast.
Jenny Dempsey (02:17.816)
to share these incredible stories and offer support to anyone considering going through or having already been through a career flip. So wherever you are in life, I hope this podcast inspires you to dream bigger, learn from those who've changed their careers, and really grab on to the changes and risks that can help you grow beyond what you ever thought possible. Okay, let's get into today's episode.
What can we learn from micro -pivots? Those little hop skips and cookie crumbs that we take and leave on the path as we navigate our career. In this episode, we meet Rob Connolly from Charleston, South Carolina, who went from VP of Sales in the manufacturing industry to starting his own business as a workplace trauma coach. Rob's journey started with helping to turn around his cousin's window and door business, which then sparked his love for problem solving and team development.
Over the years, he's made several micro -pivots, testing out different industries and roles, all while finding the work that truly aligns with his values and passions. Rob opens up about the power of reflecting on your values, being honest with yourself, and how side jobs and hobbies can really help you explore new interests before making a full leap. He's proved that sometimes multiple career flips are exactly what you need to grow personally and professionally.
So if you're feeling stuck or looking for some inspiration to make your next move, Rob's story is a full takeaway on designing a fulfilling work life, especially when it comes to addressing and healing from workplace trauma. Let's get into the episode now. So glad to have you here. Thanks so much for, for being open to being on. Yeah, I'm pumped to be here. It's a very personal topic for me. You could maybe consider me a
serial career flipper. So I'm definitely pumped to be a part of this. It's been a huge part of my personal growth journey. So thanks for having me. Yeah, absolutely. I like that term, serial growth flipper, serial flipper. That's where it's at right there. my gosh. Well, you know, I just like to jump right into it. So Rob, take it from here. Tell me, tell us about your career flip. Yeah. So, I mean, there's really about three flips in about four years for me. So
Jenny Dempsey (04:37.546)
It really began as I was finishing up my time in the nonprofit sector and wasn't really looking to make a change, was not looking for a job. And I walked into my cousin's window and door manufacturing business and they had a big need. They needed somebody who could build a website, somebody who could actually chart a go -to -market plan. You know, they really hadn't been able to do that. The main leader in the business was
doing all of the selling, doing all of the design and doing all the manufacturing with a few helpers scattered in, but there was not a consistent growth plan for the business. And so the business was in trouble. I just walked in because I was curious about what my cousins were up to. Thought it was pretty cool stuff. Went home that night, did a little bit of research about that industry and that particular segment of the industry and realized, wow, this is a potential gold mine.
One of the things that also made it really a passion for me is that it was in my hometown where the ability to create a positive employment situation in my hometown would run with the success of the business. so I built two websites in the first year, launched a new product category into the building materials industry. And we basically, went from the company being in trouble to over just sort of three years, we 10 X'd.
the revenue of the business with a 15 % net profit, which in manufacturing is really good. We changed from a beta C model where you're selling directly to homeowners to selling through a distribution network that I personally built. And for a while I was gone six out of every eight weeks across the country building that distribution network. And I was in charge of all the marketing and sales as well as all the linkages between the different parts of the company.
It was quite the experience. So, you know, that was the beginning for me. That was that moment where I took an interest in something that turned into something that I figured out that I enjoyed solving the problems and creating the opportunities. And I learned so much about myself from from that first pivot, which was not intentional. It was something I just stumbled into and found a ton of passion for.
Jenny Dempsey (06:59.148)
Yeah, that's so interesting. You were just curious about what your cousins were up to and then who knew that this was like, not only are you interested in it, but you're really good at it. Yeah. And it's like every rock I would pick up, there's a whole universe of stuff to learn underneath and a whole new industry. I was really learning sales and marketing at the same time. So anytime I generated a lead, I was the guy who had to do something with that lead.
And so it helped me really understand what quality marketing looks like, you know, generating new business from the internet, basically for a window and door company. And those first few weeks, I was also driving 10, 12, 15 hours to sell and then back to install those windows doors that I sold. So that's a lot. learned engineering skills. I learned installation skills in the window and door industry.
Learned lot about manufacturing. It was a very immersive experience. But what I learned most is that I enjoy complex situations and I enjoy helping people see their own potential. The team building that that initial effort allowed me to engage in was far and away my favorite part of that work. And it turns out that's still my favorite thing to help people find their potential. that
That was really the first moment where that light bulb went off. Like, hey, OK, yeah, I built this on -ramp, but I love this interstate highway of personal and professional growth that a growing business provides for others. That's a big eye -opening learning to come out of that when you're just like, OK, let me try this. Yeah. So there was some challenges that the industry and building materials really met with at the early pandemic.
timeframe where the supply of raw materials was backed up sometimes four or five times as long as the lead times used to be. You know, our customers and our dealers' customers had job sites that were troubled by these delays. I ended up pivoting my second pivot into the distribution side of the window and door business and then pretty quickly into equipment rental. And both of those were very, very quick.
Jenny Dempsey (09:20.95)
I didn't stick with them very long because neither of those really had that dynamic of team building and the problems that needed to be solved were really just more traditional sales lift problems. Just, you know, get people to buy on lead and that kind of thing. I didn't find that particularly fulfilling, but there's a theme through those two micro piddits, as I like to call them, that
I think it's really important for your listeners who might be considering a pivot, who are maybe in the middle of a pivot, who maybe feel like they've got a stalled pivot, who might think pivoting sounds like the worst idea ever, but they're curious. And here's that principle, it is possible, even when you don't know what you're doing or why you're doing it, to be true to yourself. The work that I kind of did on the fly through all of that was really building off of the values
that I had developed unconsciously in that first pivot of what's important to me and what gives me meaning and work and what I enjoy. And sometimes you realize that's actually not the work that I'm getting paid to do right now. And sometimes it's really helpful to just, okay, now I'm not gonna go burn the bridge and intentionally direct myself towards foreclosure and bankruptcy. this time...
There's after a while of really sitting with the fact that the work that I was doing wasn't aligned with the values professionally that I had sort of created for myself in that first pivot, there was a need to find something that was a better fit. Yeah. And so that's where the second major pivot after those two little micro -pivots really kicked off for me. About halfway through that time frame, I had started to really pay attention to what was happening in tech.
And in the early pandemic years, tech was a great place to be. Everybody was buying software to make it so everybody can work from home. The tech industry was growing almost at all costs. Growth was the whole thing. And so very little caution. Now, we've seen the ugly side of that more recently, where things that weren't realized no longer make physical sense. And the layoffs that
Jenny Dempsey (11:40.66)
And sort of the end of the parentheses have come to be the other out go of that same income dynamic when it comes to the people like me who pivoted into tech. But at that time, many of us were saying we have skills that really make sense from the sales and marketing for me and the idea of the potential of being able to build team and to engage.
for me in an industry that was all about people, which is the customer service industry. So I was given an opportunity for a couple of years to work for a company that is positioned to sell software solutions to help customer service agents be more effective and more human in their work. So that was a much closer alignment for me just right out of the gate than renting equipment or just selling a window.
That second major pivot, which is really the fourth pivot in about three years or so, was a much better alignment for me. And so as that time went on, I realized how passionate I am about working with people. And also, as I've been tracking along, my personal life was going through an enormous amount of change. And so I've gone through a lot of major changes.
all kind of within a short period of time in my personal life and realizing that there was actually quite a bit of professional trauma, as well as some other traumas that I had endured and gone through and some adaptations that I had made in order to survive, which that's what trauma is, that maybe weren't super healthy or great. And the professional side of that is pretty significantly misunderstood or not understood in the economy. think we...
We think of trauma as car accidents or major abuse or something of that nature. But, you know, really one of the main things that is traumatic about any of those things that occurred to us is our powerlessness in them. You know, where we have things happen to us and we can't stop it. We can't protect ourselves. We can't make conscious choices for ourselves. And I mean, I don't know about you, Jenny, but I've had some corporate experiences that felt very much like
Jenny Dempsey (14:01.728)
I'm not in control of my own life and how to provide for myself. And so there, I mean, really it's at the core of trauma. Any kind of trauma is when your nervous system gets overwhelmed in a way that you make adaptations in order to survive. And oftentimes that's through the feeling of powerlessness. So as I was kind of healing myself through, you know, the last couple of years leading up to this most recent pivot,
I had people, friends that would come to me and would say, wow, like you've grown so much, you've been through so much, how are you so healthy? And I would just explain a little bit about that and the tools that I've come to use, the books that I've read, the processes and patterns that I use in my daily life. And they would say, can you guide me in that? Can you help me in that? Basically, they asked me to be their coach. So I discovered that that is actually the most fulfilling work I have ever done is to
help someone heal and grow themselves with some of these tools that I've developed. So that's sort of the final pivot. Here recently, I've pivoted full -time into that role of helping people heal and grow themselves. And then I'm also helping organizations to understand what professional trauma is and how it impacts their business outcomes. So through workshops and courses and things of that nature. So that's quite a multi -pivot story.
Especially if it's like four year period of time, it's really five pivots in four years. So yeah, that's a, that's a lot of pivots in a very short amount of time with so much going on, you know, in the world with COVID in your personal life. And I'm wondering like the last pivot. So, you know, with this, the company we're with, which is actually where we know each other from.
because both in the customer service world and wanting to bring more human elements into customer service and you know, that was a job that, know, a stable income and you know, kind of like the, I don't know if it was not actual nine to five, but you know, typical nine to five type of role, great company. So when you made the decision to kind of pivot from that to do what you're doing now full time to help people.
Jenny Dempsey (16:22.658)
What was that like? Can you talk a little bit about that decision and any fears or, you know, what was going through your mind when you decided to do that? Yeah, I mean, at end of the day, you know, there's a difficulty in our society. I'd say Western society when it comes to these paradigms of what is acceptable or what is expected, the systems around us are built to reinforce that in a lot of ways. The W -2 income is
by a lender in a way that your own business never will be until it reaches you know a size that it's maybe more of a liability for you than anything else. So it's not necessarily particularly reasonable the way that that stability is looked at. Now I'm not downing stability. I'm not saying anybody's got a W -2, you know, they're just a fool. That's not what saying. I'm saying that for some of us
the need to fully align with the work that we do, it's not even like a sirens call. It's more of a source of peace within itself. Now, there's the guidance counselor statement of, if you had all the money in the world and you could do anything that you wanted and money wasn't a problem, what would you do? And I think that that can be a helpful question, but it can also be an unhelpful question because most of us spend most of our time trying to avoid bad outcomes in life.
And we spend more time trying to prevent the things that we're afraid of than we do actually building our life the way we want and so I think that's been the big shift is for me I Don't want to live that way anymore. I don't want to live in this box of Okay, well if I Risk than this if I risked in that I want to live in a way
that feels like I'm alive in everything that I'm doing. And a lot of people in our society would say, well, that's just a pipe dream. And I would say that there's degrees of this that you can do no matter what your job is, no matter how you feel about your job, that you can actually design your life within those parameters to a certain degree. But for me, it's that very message that I just shared that is my greatest alignment. And it's not just my coaching business, it's...
Jenny Dempsey (18:42.134)
It's my music as well. I'm a musician and I write and record and share my music on most of the streaming platforms. But, you know, it hit me one day, I was commuting downtown here in beautiful Charleston and it is really beautiful despite the humidity that we get about. But we've got this beautiful bridge where I cross every day, or I used to cross every day when I was commuting to the office downtown.
And for a few months out of the year, we get some serious condensation on the windows because of the humidity here. And about five, six minutes into the drive, the sun starts to bake off the condensation. And one day I'm doing that thing that most of us are used to doing in the commute. And I've got my coffee. I'm rolling down the windows. And I realize that there's thousands of other people.
on this road and we're all doing the same thing. And some of us are pretty aggressive about it. Like I gotta get here now. I gotta get, gotta cut in of this person. I'm gonna get, I'm gonna save 3 .3 seconds by risking everyone's life, by cutting across two lanes. And there's all that whole, and it just occurred to me how mindless it all can be. Not that it is for everybody, right?
But it's easy for it to become very meaningless and very mindless and very unconscious. So there was just a part of me that said, I want more. I want more. And so actually a song that I wrote out of that talks about how that feeling inside is like a neon sign telling you that there's supposed to be more. And it starts literally the first verse is about the condensation and the caffeination and the lemmings fighting each other to get to work just two minutes early. And it's a bit of a
commentary, but and I would say if you are genuinely present with yourself and you are pleased with your work life, then you should keep doing it and you should enjoy that. There's nothing wrong with what fulfills you for work. There's not one right way, but there's also not one right way. And, you know, for many of us, we're just not wired to do this. I was looking at my second grade
Jenny Dempsey (21:02.668)
report card the other week, I went to visit my parents and, and this poor teacher, you know, I was really never a good conformist. It appears, you know, Rob's doing well academically. We will work on other things was kind of how she started. want to see this. It's always been a part of me, right? there'll be a, there'll be a LinkedIn post soon on that. But there's always been a part of me.
that just needed to explore, needed to understand, needed to connect. And so this last pivot has really been about finding that full alignment for me that allows me to help others find alignment for themselves. Wow. Yeah. And you mentioned earlier the micro pivots. And I want to hop back to that for a second because when I'm hearing you tell this story, Rob, your journey,
where you are now, like those micro -pivots were such a big part of it. And it sounds like it really helped to kind of fine tune your values. Like you knew, like you're like, yes, these are the things that I really enjoy. But it wasn't, it almost like it, you had to kind of step into those other roles that you're like, okay, yeah, no, I can do this, but it's not really where I want to be in order to kind of continue down the path of where you do want to be. And I think a lot of the people listening to this with career flippers, we
You know, we think it's, well, I mean, even myself, I get caught up in the trap of this like very black and white thinking point A, point B, you get from one place to the next. And there's not, there's so many steps in between and so many of these, which I love the phrase, micro pivots in between that we have to do, whether or not we like them, we have to kind of do this to really figure out who we are, how we want to show up in the work that we.
that we want to do. And I don't know, I just think that that resonated with me a lot because there's so much more than just one step to the next step, right? Yeah. mean, in my parents' generation, the idea of pivoting your career was almost like jumping off a cliff. Why would you do that to yourself, basically? No parachute. are you thinking? But there were also pensions and
Jenny Dempsey (23:24.942)
there was a whole different viewpoint of society's continuity. I mean, the research out there about the distrust of society with large institutions and businesses, the simple fact is it ain't the same world. you know, for those of us that are finding ourselves on the journey, we have to recognize that that is a journey. And, you know, it's not the squeaky clean college degree equals 40 years equals
Gold watch, corner office, And that's just not the way our economy functions anymore. And so within that, and I would say also the pandemic kind of had a two -edged sword effect on this dynamic, but within that, it is way more normal, way more accepted for people to change jobs more quickly than it used to be. And when I say the pandemic was a two -edged sword in that way,
I mean, in some ways I'm a perfect example because I pivoted into what appeared to be the only place you really wanted to be with tech where you got unlimited PTO, you work from your living room and your underwear if you want to. remote life. Yeah, you know, but then there's this 30 % of us that are left over at the end going, wait a minute, we moved out of an industry that
no longer exists maybe in the same way that it did when we left it. And now the industry we moved into has majorly shifted or left us behind or needs less people, especially with AI moving in. So I think the theme in the micro -pivots is openness. And it's openness to yourself mostly. Each of those micro -pivots that I did, I gave everything that I had to understanding that job, understanding what was needed of me.
And I wasn't in either of them very long, but I feel great about my investment in that work and in myself that helped me to understand, hey, remember those things that used to really fulfill you in that last role? How do we get something that's a blend, you know, that has some of these things that has the ability to grow into what aligns with your values better? But there's an openness to yourself.
Jenny Dempsey (25:45.802)
in that process and the ability and willingness to even reflect and not just clock out. Because here's another thing that I think is really important that has helped me a lot. I used to think, as many of us do, that we have a professional self and we have a personal self. And they're really not the same people. know, many of us even put on a different persona when we go to work. Many of us are forced to, in some ways, behave in ways that are not really
us when we go to work, but what happens at work is happening to us. And what happens outside of work affects who we are when we're at work. We see this in a large way in the way professional trauma impacts life at home and the way that our whole life and things that we've been through impact our performance and our ability to relate well and be stable at work. And so it's a false dichotomy to
to separate the personal and the professional self fully. Not to say that we don't have skills that we don't use at home that we use at work. Not to say that there isn't a part of our personality that's more expressed at work or at home. It's not to say that we're literally identical, the same exact expression of ourselves. But for me, enough pivots in a short period of time starts to give you a common thread that kind of gets sewn through that.
And I'm not necessarily recommending we try to set the record out there for how many pivots you can have. There's certainly some downsides to that. But there's some real beauty in that as well. And I would say it's possible, even if you've been with the same company in the same role for 30 years, to actually sit and reflect, what are the things that have been most fulfilling? And what are the things that I have also been the best at? And where do those two meet?
You know, the beauty for many that are considering a pivot today, and I'm sure some in your audience are this way, is that there are more opportunities for side hustles that can turn into something bigger, but they don't have to, than there has been. So you can almost dabble at your pivot before you go off the cliff all the way. And especially if you're aligning your pivot with the reflection of who you believe that you are professionally and personally.
Jenny Dempsey (28:11.702)
over the course of your career, then doing something that gives you a little extra, you know, Mason jar money on the side, you know, maybe it pays for your vacation, you know, to start, but you know that it's work that you love and that makes that you're effective at while it makes you happy. That can be a really healthy way just to get maybe you're wrong and you actually don't like that work, but you didn't go all in. Right. And so I think there's a lot of
sort of just common wisdom that seeing those values and that common thread can give you. And those micro -pivots were those opportunities for me. Yeah. Yeah. I hear it from a lot of people about the side hustles or wanting to make time for those things that they enjoy and wanting to do it just as a hobby, but not doing that because they're so, you know, pressed for time with work and work comes first. And I know this firsthand for myself as well because
I would just put all my creative pursuits on the backboard. Nope. And work comes first. friends wanna hang out? Nope, I gotta work. And then it's like, wait, what's happening here? And so to just set boundaries and make that time and hearing how you said that, it's like, it doesn't have to be jumping off. You can do a little bit, you can make the time and you can figure out, do you actually like this? Or is it something that maybe you're like, all right, I'll do this every so often. You can kind of figure that out.
and you just have to try it. It's a journey of exploration, you know, and unfortunately what has happened for many of us is in the way that the economy has gone and society has gone, many of us are not in a financial position to do a lot of experimentation. Yeah. True. Or at least we believe that we are. And so, you know, I'm not advocating your responsibility here, but I do want to just, you know,
throw out there that you do have choices in your life. And, and, and we don't often live like we have choices. And, and so I think that that is one of the things that does not benefit most of us that are workers in the economy that are actually producing the most value for those who benefit the most from that work is that we feel we don't have any real choice.
Jenny Dempsey (30:33.518)
And so I would just say, I'm going to plant the flag of that's not true and encourage people to open themselves to themselves and have times of reflection. And I have a lot of coaching clients where this is what we do best together is really reflecting on those common threads of values and helping them to design their work life in a way, whether it's a, you know, a new role.
whether it's within the role they're staying in, whether it's adding a side hustle, whether it's going all in on something that's completely different. Once you find yourself within your work and find alignment with yourself within your work, it doesn't have to be a four letter word anymore, even though it'll still have four letters in it. It doesn't have to be this thing where you're literally dreading it. And it's like, dang it, I can't work. Redefining the four letter word, shifting our mindset on it.
So there's a lot of topics here that I feel like we could talk about for a long time, Rob. Thank you so much for taking the time. I really want people to connect with you. I feel like there are so many opportunities to work with you, to learn from you, to hear your music. How can people find you? How can they connect with you? Yeah, absolutely. So I'm on LinkedIn. That's a good place to find me. Rob Conley, it's R -O -B -E -C -O -N -E -L -L -Y. And then
For the coaching stuff, you can find me at TurnStyle Coaching. And I do just want to mention what the turn style is all about real quick. So this idea of the turn style, I'm going to do a little show and tell. I know you might not be able to see it because you're probably just listening. But if you literally Google turn style, you'll be looking at the same thing I am. And the turn style symbol is from the study of language and the study of computer science. And the idea is that everything that we need to know to move forward
we already have the foundation for it within us. And so the way that I help people to think through that is that you know everything you need to know to design the life that you want. You just need to know yourself. And so turnstylecoaching .com is where you can find me there. And you can just search for my name on Amazon Music or Spotify or Apple Music, wherever you find your music, and you'll find my music there. Thank you so much, Rob. I appreciate you being here today. It was fun, Jenny.
Jenny Dempsey (32:58.2)
Thank you.
If this episode gave you a little boost, share it with a friend who could also use some inspiration. Rating and reviewing the show helps more than you know, and hitting that subscribe button means you'll get more amazing flippin' stories like Rob's every Thursday. Your support helps me reach even more career flippers and those dreaming of making their own leap, spreading all the good vibes and motivation that we need on this journey is necessary. And if you're maybe looking for a career flipping speaker at an event, wanna sponsor the podcast,
or just want to say hi and share your career flip story, pop on over to thecareerflipper .com. I'd love to hear from you. What I love most about doing this podcast is the hope that it might inspire you to go after what you're dreaming of, even if it feels scary right now.
I know it's really hard to take that first step. Trust me, I'm there right now when the fear of the unknown is really holding you back. But if I could ask one thing of you, it would be to tie your shoes, take a deep breath, and just start. You never know where it might lead, and I believe that you can achieve anything you set your mind to. So keep on your path, my friend. What's the best that could happen? Talk to you next week.