How to Make a Mid-Career Change (Without Blowing Up Your Life) w/ Jake Kennington

Every man hits a moment in his career when he wonders: Is this really what I’m meant to do?
In this episode, Don sits down with Jake Kennington, a structural engineer turned coach, to talk about how men can recognize when it’s time for a career change — and how to make that pivot wisely. You’ll learn:
 • How to know the difference between a rough season and a wrong path
 • Why success on paper can still leave you empty
 • How to redefine success and build a life that fits your values
Guest Resources
 🎯 Jake Kennington — Actively Human
 Website: https://activelyhuman.com
 Free “Own Your Life” Playbook: https://activelyhuman.com/#playbook
 LinkedIn: https://www.linkedin.com/in/jakekennington
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Question for You
 What’s one area of your career or life that you’ve felt restless about lately? Drop it in the comments — your story might help another man find the courage to make his next move.
⏰ TIMECODES
 00:00 Introduction to Jake Kennington
 01:12 Jake's Career Journey and Realization
 04:20 Navigating Mid-Career Transitions
 12:03 Redefining Success and Personal Growth
 18:34 The Role of Creativity and Experimentation
 28:58 Building Connections and Coaching
 40:59 Conclusion and Contact Information
HASHTAGS
 #ManhoodTribes #MensGrowth #CareerChange #MensLeadership #PurposeDrivenWork #FaithForMen
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Transcript

Don Ross 0:01

Man. Have you ever gotten to a place in your career where you're completely dissatisfied with what you're doing, but you don't know if that means you should really make a pivot in terms of what you're doing for work, or just figure out how to make things work where you're at? I'm really excited today for, uh, my guest who's here, who's gonna tell us a lot about mid-career transition and what all that looks like. Jake Kennington is a licensed structural engineer who spent over a decade designing a hundred million dollar buildings and climbing the career ladder only to realize that success on paper didn't match the life he wanted to live. As a husband and father of four, Jake went through a personal transformation. Rebuilding his health, restoring relationships, and redefining success on his own terms. Out of that journey he founded Actively Human, where he now helps mid-career professionals to redefine success and realign with what matters. So they're energized at work and excited to come home each day. Jake, welcome to the show, man.

Jake Kennington 0:58

Thanks Don Appreciate it I'm glad to be here and it's been a pleasure getting to know you over the last couple weeks and be on the show

Don Ross 1:03

Yeah. Excited to have you here. And I think, uh, the guys watching and listening are really gonna benefit from what you have to share with us. So let's get started. I want to hear from you a little bit about like what it's like being a full-time structural engineer and what led you to the place of just saying eh I don't think this is actually what I want to do with myself for the rest of my life

Jake Kennington 1:25

Yeah it's a difficult transition I think a lot of people even if you're not an engineer a lot of people get seven to 10 years into their career And they climb that proverbial mountain Maybe they're not at the top but they're they're at a summit and they look around and they go man this isn't as satisfying as I thought it would be And this is no knock on the engineering career or any structural engineer It's just you change life changes Um I started my journey as an engineer back in 2000 let's see would've been 2010 I graduated in 2014 from Fresno State So even with with my uh schooling in college and and my work experience after that um you know I'm a different person than I was back in 2010 I've got four kids I'm married and and life changes And so it it wasn't necessarily that the industry is bad or or it was a wrong fit I don't feel like I got duped or or tricked or anything like that But I just got to this summit again this this uh top of the mountain so to speak And I looked around and I said you know what This this isn't really for me And and the way that I knew that Don was I looked at the people 10 or 15 years ahead of me and I said they might not be miserable but if I do what they're doing I'm gonna be miserable And so I quickly saw that I'm like okay we need to we need to pivot here and do something different I think a lot of your listeners will empathize with the thought of knowing that they want something different and they want something more But they don't know what that different or what that more is and that's how I felt Uh maybe four or five years ago I was just like man I need something different and I want a little bit more but I didn't know how else to put that into words

Don Ross 3:12

I think I think that feeling is totally relatable especially for guys who are I would imagine probably in the like 35 to 45

Jake Kennington 3:20

Mm-hmm

Don Ross 3:20

You know like have uh exactly what you said you know have invested a lot in their their current career or maybe their current company that they've been with And are just kind of looking at it going is this all that there is like not only to their career but also to their life Like is this really where I'm I'm headed Um and yeah I think uh I mean you know my story is a little bit of the same I mean I had Si kind of a a similar uh dissatisfaction and um you know kind of confusion over like able to look at like the people who were at the top of the of the kind of the ministry career that I was a part of and going I don't think I want that life I'm not really sure that that's for me but also kind of left with a feeling of like What else is there Like I've invested so much into like knowing how to do this career that I'm in like how would I even think about doing something else You know So tell us a little bit about that for you Like you got to that kind of place of like eh this is not in the mountain I wanna keep climbing Like what do you do at that point

Jake Kennington 4:21

Yeah So um that's a great question and and it's different for everybody um given their circumstance their their their life whether they're married or have kids or they're single I mean when you're single and you're not married and don't have kids it's really easy to just pull the para cord or pull the parachute right and and start over Uh me with four kids and and a family and a mortgage and everything else it it wasn't necessarily something that I just Exactly Yeah You're kind of you've got some some things tying you down in in good ways Right Um and so for me the the difficult or the frustration part of that whole story was that I felt like I had all my eggs in this one basket in my career that I had spent you know 15 years pursuing And I felt like I wanted to do something a little bit different I didn't know what that was but I also felt like it would be starting over So what I had to get over in my own mind was that it wasn't an either or decision It could be a both and decision What I mean by that is I didn't have to quit my job and work for myself the next day

Don Ross 5:26

Yeah

Jake Kennington 5:27

So um long story short I I worked for a firm an engineering firm in Fresno California for 12 years I left that firm moved my family 800 miles to Salt Lake City Utah Took another job two years later told my wife I want to go back to the firm in California And she's like what are we doing Um so she's freaking out Yeah exactly She's like what What is the plan here The reason I went back to the firm in California was because I had an opportunity to scale back my engineering I went from five days a week to four and when I tell people that they go oh four tens and I go no I work four eights so I work 32 hours a week as an engineer and then one to two days a week I get to work on actively human my coaching company So it was a solution for me to transition a little bit more slowly into doing both but also not having two 40 hour a week jobs like that was not on the table for me I was like I I don't wanna work 80 hours a week

Don Ross 6:26

Yeah

Jake Kennington 6:27

I had to get really creative on how how can I do both but not sell my soul to my job You know what I mean

Don Ross 6:36

Yeah Uh absolutely But I gotta say as as soon as you're saying that I like I have to ask um how did you pull that off Can you please share your secret sauce with the rest of us of how we go down to the magical four day work week

Jake Kennington 6:50

Uh again I I'm not arguing that this is the solution for everybody I think the overarching principle is be creative and don't don't necessarily fall into the trap that it's one or the other that I have to quit my job right now and I need to do something else that we can experiment with other things maybe scale back the time commitments that we have currently if that's not what we want to do To answer your question though I won't beat around the bush I I went back to the firm I left uh luckily I had not burned that bridge left on good terms Um and I spent over a decade with these people They they were good friends and and I considered them family Um so when I reached out to them and I said Hey what would you think of me coming back They were like wait a minute You you're gonna come back Like they it was never on my radar to come back and they felt that um but they welcomed me back with with open arms and and I got really lucky I was strategic but I was really lucky I was willing to take a pay cut so I was gonna go to to four out of five days a week 32 hours So I was gonna lose in my mind one fifth of my income and my idea was to start this other business and supplement my income with that I was like if I could make you know 20 grand this year doing this other business then I'll be at a a a net zero Right Like I'll I'll be a a no net lost But um I I again blessed lucky whatever you wanna call it we negotiated for me to actually not lose any of my salary And I actually made a little bit more money working four days a week instead of five And so I feel very blessed and very fortunate Um my Fridays are kind of my my day to spend on my own business I treat those days as sacred man because I I fully realize that I'm very blessed and very lucky But again I'm not trying to paint a roadmap for exactly what people should do

Don Ross 8:41

Yeah

Jake Kennington 8:41

just saying get creative and and and discard this idea that it's one or the other Maybe there's a solution that you could do both

Don Ross 8:50

Yeah I like I like that I like the creativity of it and I like the fact that um you were willing to just ask you know it takes uh

Jake Kennington 8:58

Yeah

Don Ross 8:58

do that you know Uh I think that's something that a lot of guys would um avoid for one reason or another You know like either out of fear of the hard conversation or out of uh pride of not wanting to go back to their former employer And you know kind of like Al it's not really begging but just kind of like asking for something that you willingly gave up Uh you know that's hard for men to do I think So kudos to you for having the courage to be able to do that and that it worked out in your favor You know I I think it's great Um but I think it does just speak to that idea of um exactly what you're saying you know it's not one or the other Mid-career transition doesn't mean just like jumping from one ship to the other It it probably is something of a transition for anybody who wants to be able to pull it off Um and I think you you kind of got creative about how to make that transition work for you and your family and that sounds like it's been a win all around

Jake Kennington 9:51

I have one thing It's it I agree with everything you just said but it it's really easy for me to tell this story and and focus on Going from five days a week to four and that kind of happening overnight But the the whole story that I shared is you know I started at a firm I realized that I kind of wanted something different or something more I left it took me two and a half years to figure out that I wanted to go back

Don Ross 10:13

Yeah

Jake Kennington 10:14

Uh I moved my family 800 miles They're all in my kids are all in new schools My wife has to make new friends It wasn't this straight line It's you know it's not often something that somebody can go do tomorrow But what you said is like Try something uh ask uh get creative and and figure it out along the way And a lot of times there's more zigs than zags as opposed to like the straight up into the right kind of trajectory But eventually those zigs and zags lead to where you wanna go

Don Ross 10:44

Yeah No that's great okay so related to that like um you know I um I did not follow your wisdom at all when I was in the midst of my mid-career transition I very definitely jumped ship and

Jake Kennington 10:57

Sure

Don Ross 10:57

and tried to just you know land on my feet as best I could I did all right but uh it was scary and uncertain and not something I would wish upon my enemies Um you know and you know I fought myself for wishing it upon my wife but Uh you know we made we made it through Um but it was not ideal And I I think some of the um the advice that I had been given that I ignored was um don't run from a job run to a job Um and uh you know I kind of ignored it because at least in my situation like I was in a lot of Pain The the job reality that I was in was just kind of no longer tolerable And I was just at a place where it was like I it's not just like that I don't want a future here It's like I don't want this present here anymore You know I I I can't really uh endure this anymore but I I would kind of like ask you Do you think that's sound advice that idea of like don't run from a job run to a job um does that still hold weight in kind of the job market today Would you advise people in the same way as they're thinking about a transition Like how how would you kind of go about that

Jake Kennington 12:03

Yeah what I'd read into that con Don is there's a proactive nature to what you just described when you're not running from something but you're running to something you're kind of intentionally deciding what to do next as opposed to just reacting to a horrible or a toxic job or whatever you wanna call it Um there's a time and place for reaction We all need to react Right And if if there's a job that's just not not good for us then then yeah get outta there and again Circumstance uh and and context is important here Whether you're single or married or have kids or at the end of your career or financially stable whatever it may be uh gets a little complicated But I think the preferred approach like you mentioned would be be intentional and proactive and run to something as opposed to away from something But uh the hardest thing about that Is what do you run toward

Don Ross 13:03

Yeah

Jake Kennington 13:03

And that sounds like a really simple statement or question Uh in my experience myself included most people don't know what they want

Don Ross 13:12

Yeah

Jake Kennington 13:13

Um

Don Ross 13:14

really wanted to hear that from you uh as you kind of you know came to that conclusion of I I look at these other folks in my industry and I know that that future path probably isn't the future path for me How did you figure out what you wanted your future path to be

Jake Kennington 13:32

Sure Yeah It's it's it's Sometimes very clear for some individuals or at least at Pierce So from the from the outside you're like man that guy really knows what he wants you know Um but my experience has been that most people have a hard time um putting that into words and being super clear about what they want from life And so this is a big part of what I do with actively Human is I I kind of uh have a three pillar system or a three-pronged system of redefine Realign and reconnect So the redefine the first part of that is redefine what success means for you I think it's really easy we all do this to simply follow the leader whether that's your parents whether that's your boss or your coworkers and just kind of like Get used to the day to day and do what everybody else does We're we're all individual We we all have our own different characteristics and traits but if you looked at like just a company that you work for and where you fit in like you you're kind of like a lot of the people that you work with For the most part You just kind of follow suit and you you there's status right And so when you ask people like what does success mean I love the word success because it's so vague If you ask 10 people what is success You would get 10 different answers right Um it might be achievement it might be some sort of career path It might uh entail some definition of happiness or something like that But for me I had to get really clear on what does a successful or good life look like for me Um There's this quote the difficult part about this There's this quote from a guy named Harus I think his name He is like 2000 years old one of the ancient Greek guys and he says something along I'm gonna butcher it but paraphrasing He says uh no man ever steps in the sand river twice because the river's never the same and neither is the man And so the river is life Like we all go through different phases of life It's always changing Just like when you step in a river it's always gonna be a little bit faster or slower or or deeper or whatever it may be But the person like you you're changing as well

Don Ross 15:38

Yeah

Jake Kennington 15:38

So my definition of success might have been different In 2010 when I decided to study structural engineering I wanted to become a structural engineer So I was gonna get the degree I was gonna pass the exam I was gonna get the the work experience and I did all those things But the funny thing about that is when I got to that pinnacle to to getting my license it took me 10 years to do that I start even before I passed my test I I started to have these feelings of like well what's next You know like what am I gonna do next And so what I learned for me is that success cannot be a destination Because if it is a destination then when you get there what happens Like you're just done like you know what's next

Don Ross 16:22

Yeah

Jake Kennington 16:23

And so for me success is a compelling future I help people in my group coaching program define what that is for them There's a lot of similarities amongst people in in the group but there's also very unique definitions of what success is And I know that's a very high level definition of what is success but for me a compelling future is like spending time with my kids uh having freedom of time to work on the projects that I wanna work on starting a business That was a big one for me I hired a coach uh two years ago now my first coach I ever hired his name is Richie Norton and he helped me understand that I want to be an entrepreneur And for 30 plus years of my life I thought the exact opposite I thought I would never be an entrepreneur cause my dad was an entrepreneur and I had a front row seat to that and my little child brain thought

Don Ross 17:18

I

Jake Kennington 17:18

dad's never around And we struggled with money

Don Ross 17:22

Hmm

Jake Kennington 17:23

and I don't want that In fact my dad told us kids we have six kids in my family he would tell us go get a get a college edu education Get a nine to five job get the benefits that's the safe route But in the end of that sentence with the same breath he would say but I would never work for anybody else

Don Ross 17:40

Yeah

Jake Kennington 17:41

And what I've learned as an what I've learned as an adult is he wasn't pushing us away from entrepreneurship He was just letting us know that this isn't easy

Don Ross 17:50

Yeah

Jake Kennington 17:50

And if you want it and you wanna do it do it but only if you want it And so that coach helped me kind of switch my thinking there and realize that success for me was working for myself Now that's not true for everybody but what is true is you have to figure out what success looks like for you

Don Ross 18:09

That's great Um so okay so walk us through then a little bit of like once you had some sense of what that was for you how did that kind of take fruition as uh okay I need to start this business and it looks like coaching and or you know like how did you begin to kind of formulate in your mind this is what I want this is what I wanna do and this is kind of the shape that it's gonna take

Jake Kennington 18:35

Overall this whole process has been several years four or five years of you know getting coaching reading books working on myself figuring out what success means But the last two years specifically is the timeframe that I've done the coaching What I would say to your audience is everybody wants clarity Everybody wants to know what to do next Um my experience is that more often than not uh you can find clarity but it's only the next step You you you oftentimes don't get an outline the next three to five years and be like this is what my life is gonna look like It's like what do I do tomorrow What do I do this week What do I do over the next six months What's the next step that I could take towards this future that I think I want cause part of it is you define success whatever that is for you and then you take action And like I said there's more zigs and zags than there are straight lines So my story was I became a book coach for like a couple months I was gonna teach people how to write books um that went like this real quick and and it didn't work out And so there's a lot of Failures that occur along the way Um but what I would say is just figure out what you want from life and take the next logical step And that's the way that you get clarity That's where clarity comes from It comes from action not planning

Don Ross 19:56

I I've loved so much of what you're saying uh in that process because I you know I think um I I know for myself personally but I think for men in general you know this idea of like man we would really just love a roadmap Right

Jake Kennington 20:12

Yeah

Don Ross 20:12

just please tell us what the steps are we'll be happy to follow em You know like I can I can stick to a plan Could somebody just please

Jake Kennington 20:19

Yeah

Don Ross 20:20

me what the steps are And uh life unfortunately just doesn't work that way You know uh a lot of what I talk about here on the Manhood Tribe Show uh even coming from a a faith perspective is our relationship with God often doesn't look that way

Jake Kennington 20:33

Mm-hmm

Don Ross 20:34

we would really love if God would just kind of like lay it all out for us like tell me the things that I need to do and I'll do it Um and he kind of refuses to do that for us and I think there's a lot of reasons for that I think some of that from a faith perspective is that he's more interested in relating to us than in just providing us with The things for us to do And so by uh by you know forcing us to relate to him in order to be able to get answers it it maintains that relationship which I think is really key and important for us as men to realize that like the goal of our faith is is not about just obedience it's about relationship And that makes a big difference Um but at the same time I think even if you're not coming from a faith background I think what you're saying is just you know like as men we so kind of hungry For the the blueprint right The the engineer's blueprint to be able to just tell us like here's what the final product is gonna look like and here's how you're gonna get there And that's just not the way that things work in life And so to be uh to be successful in this process is recognizing like It's gonna look different than you think it would The final product probably isn't gonna be what you anticipate it being at the beginning Um there's gonna be failure along the way Right I I think you just kind of mentioning that of like I tried something and it tanked was no good at all Uh you know that was kind of a similar experience for me Stepping out of the ministry world and trying to you know make a change there Uh my first kind of foray into this like online business entrepreneurship world um didn't didn't launch so well you know it didn't go like I had planned on it going or like I expected it to go And so trying to figure all of that out I I'm just learning that that's like that's not actually an indication of I've done something wrong It's just simply an indication of I've gotta pivot I've gotta learn I've gotta try again I've got to do something different And it's like those things come real intuitive to us when we're in the very early stages of our career But something about like trying it again at mid-career point it's like those those muscles aren't there anymore You know Like we don't want to do that We don't want to fail we don't want to try things We're not used to trying like uh it just gets so much harder to do all of that So like what have you done to be able to Handle that To handle the you know the complexities the failures the um you know the like curve balls the just all the things that have come your way in ways that you haven't expected What's helped you to be able to kind of hang in through this wild process

Jake Kennington 22:59

Yeah so that's a great question Don Um I mentioned a guy named Richie Norton He has a wonderful book called Anti-Man I read that book uh before I knew the man um I was thinking about he's he's a coach I was thinking about hiring him to do some coaching and ironically I ran into him at In and Out Um I I saw him standing there I was there with my wife and I'm like that's like that guy that I read his book Um and he is a real human It's always fun to meet your heroes Right And um I walked up to him and I totally blinked Like I I I said my name's Jake nice to meet you And I he's like I don't know who you are I couldn't I couldn't remember his name I'm like you wrote that book you know and he is like Richie Norton And he stuck out his hand and I got to meet him He was fantastic But um Since then I ended up hiring him as a coach And he has this really awesome framework um that kind of answers the question that you just asked He calls it the four P framework And the four Ps stand for the four priorities And so oftentimes what happens is especially as fathers or as men we have a lot of priorities We have a lot of things on our plate We gotta pay the bills We have jobs we have families we have children we have hobbies Hopefully we have other things in life That we're doing And he said a really easy way to stay focused on what's most important cause the battle that we have is is between what's urgent and what's important Another definition of success for me is success is choosing what's important over what's urgent Um and oftentimes we think things are urgent but they're not so urgent But he he has he has a really easy framework to define what's important to you So he says take a piece of paper write these four words down And I did this with him And it got me really clear on on what was important to me He said write down personal people Play and professional those four categories And then under each one of those words write down any responsibility or priority that you have Just write a ball down You might have 20 in each category so you got 80 total And he goes circle the top most important one in each category so you'll have four Now that doesn't mean everything else doesn't matter What he's saying is you can work on those four most important priorities right now So that's your next step right

Don Ross 25:21

Yeah

Jake Kennington 25:21

And then you create a project around those priorities So if your physical health is is something that you've neglected which is something I found myself doing um the first 10 years of my career is you just kind of grind it out and work and study and put in the late hours And then you look in the mirror and you're like man I could lose 40 pounds because I'm not very healthy I'm pushing 40 next year You know Um and so my physical health right now is one of those projects I I do this regularly I I do the four P exercise I I figure out my top four priorities I create a project So my project right now around my physical health is my name for it My cheeky funny name is Dad Rod or I can't even say it Dad bod rad bod Um and so and I have metrics I have you know a diet that I'm following and so many times a week I go to the gym and whatnot But it's a it's a project and it has a timeline You know I'm doing it for six months or whatever it may be And I work on those things on a fairly regular if not daily basis

Don Ross 26:18

Yeah

Jake Kennington 26:19

And I encourage people in my coaching program to do the same thing We go through this exercise what are the four things People personal play and professional Write em all down circle the top one create a project around those and do those And it's funny when people say I don't have time for that And you're like you just told me these are the most important things in your life and you don't have time And what Richie's really good at this this mentor and coach that I hired and kind of use his framework What he's really good at at at helping people understand is we often don't have a time problem We have a priority problem So we're just not making time for our priorities We say they're important and then we don't do them right So there's a disconnect or a misalignment And so for me to answer your question that's been super helpful to try to just get things off the ground is like do these little things that are more project based cause projects succeed or fail right Like I might have a professional Projects that I'm working on and I put a timeframe to it and I say I'm gonna do these things and it doesn't work Like the book coach thing right That was one of my projects for a while and it didn't work That's okay You know what I mean I learned a lot along the way I learned that I don't want to do that And so uh when we treat it like that kind of temporary or or let's see if this works out Or let's see how this turns out Then there's a lot less to lose because it's not about the destination Again it's not about the achievement it's about the journey right

Don Ross 27:53

That's great No I I love that Uh I love the the aspect of creating those kind of projects for yourself

Jake Kennington 28:00

Mm-hmm

Don Ross 28:00

in our manhood tribes world we we call those manhood challenges Uh

Jake Kennington 28:04

I love it Yeah

Don Ross 28:05

a way to to force yourself to keep Working on something you know keep getting better at something that actually does matter to you And uh yeah I I I love that uh just those categories I love the um the emphasis on it's a priority issue It's not a

Jake Kennington 28:22

Mm-hmm

Don Ross 28:23

Um you know just uh having somebody else in your life just be able to tell you that too is is super

Jake Kennington 28:29

Yeah

Don Ross 28:29

just to remind you

Jake Kennington 28:30

Yeah

Don Ross 28:31

You know if you really wanted to you could find the time for it You know if it really was the priority that you're saying that it is you could and would find the time for it So

Jake Kennington 28:39

Mm-hmm

Don Ross 28:40

I think that's um that's that's super helpful perspective Okay So uh you know where do you go from there Like where do you start to gain some traction You know the book coach thing kind of falls through How do you how do you pivot from there And you know what what does that pivot kind of look like

Jake Kennington 28:58

Yeah So for me uh like I said there was a a couple of failed things along the way trying to figure out there's a lot there's a lot of self-doubt that happens day to day There's a lot of like What the hell am I doing kind of mentality and and will this ever work Um but at the same time it's it's a rollercoaster but the next day you you have some small win that gives you so much confidence in what you're doing And that might be you know for me it was writing Um I write a a weekly kind of a newsletter kind of thing Um I I don't necessarily do it to to grow an audience or anything like that although that is part of my business I have just found a new uh a new love for writing Forgetting my thoughts onto the paper and editing that and making it into something um that I enjoy it It's not easy It it's something that I love even though it's hard it's like running for me Like I I you never see me smiling while I'm running Like I'm out there running and I'm miserable Right But after I'm done running I'm like I

Don Ross 29:57

anyway The

Jake Kennington 29:58

yeah Yeah

Don Ross 29:59

it's like

Jake Kennington 29:59

Oh they're the worst They're the worst Yeah And so I'm sweating I'm frowning I'm grumpy But when I get home from a run I'm like man that was really good And it's the same thing for writing Every day I sit down to write I'm like oh this is so hard Um but every time I do it I I find great peace Um and a lot of learning that happens in that reflection And so for me it was finding little activities like that that are like Hey writing this newsletter could help my business But even if it doesn't I would spend my time doing this anyway

Don Ross 30:31

Yeah

Jake Kennington 30:31

I often tell people like if money wasn't an issue let's just pretend like money wasn't an issue What would you do

Don Ross 30:38

Yeah

Jake Kennington 30:38

With your time and oftentimes it's like okay well maybe there's a business opportunity or maybe there's a way that you can scale back what you do for your career and spend more time doing that even if it's not a money maker Right My my neighbor I just talked to him the other day he's in tech I don't know what he does because he's in tech and who knows what people in tech do but um

Don Ross 30:59

so true

Jake Kennington 31:00

he Right Oh I'm in tech I'm like I don't know But um he probably says the same thing about engineering but I said what would you do if money wasn't an issue If you your mortgage was paid for and you could take care of your family what would you do And he is like oh I'd teach and I never want to come off as like um judgmental or or anything like that So I had to say it very lightly but I was like well maybe you should try doing that in some capacity Whether that's through the church or whether that's like an adjunct professor or maybe even in your profession Somehow if you could teach on a regular basis it's like don't wait till you retire to do the things that you want to do Like scoot that timeline up and start doing those things now So for me to answer your question again it was writing this newsletter It was realizing that I wanted to be an entrepreneur Slowly but surely figuring that out Um for me coaching it's like okay I'm gonna coach somebody Um but I've never done this So how in the world do you tell somebody Hey hire me as a coach even though I've never done it Right So for me again it wasn't an either or It was more of a how do I do this kind of simultaneously And so I called a friend that was an engineer that I used to work with and he was going through a tough time I was really close with him but he was trying to Look for a new job and and trying to figure out what was next for him kind of this mid-career crisis right And I said how how would I'm trying to grow this business I wanna become a coach I think I wanna become a coach I'm not sure What if I called you once a week and we just had like a a chat for an hour and I could be your coach but you could also help me with some things and and it would be very casual And he said yeah we did that for almost a year

Don Ross 32:42

Yeah

Jake Kennington 32:43

Um And so I learned a ton He got a new job He's a lot happier It wasn't anything that I did or said but again like you mentioned it's it's nice to have somebody to talk to and and voice those frustrations with And and also it's hard to read your own label You know uh people can see you from the outside and oftentimes ironically Understand you better than yourself sometimes in certain situations And so it's good to have a sounding board and um so that's kind of how it started That that that was kind of the next step to answer to answer that last question

Don Ross 33:18

I man I uh again I just think there's so much wisdom here I I think you're you're Your question your very clarifying question of you know what would you do if money wasn't the issue

Jake Kennington 33:29

Mm-hmm

Don Ross 33:29

take money off the table I think that is for I think for men in particular That's that's so helpful Because you know money is an issue right We're we can't pretend like it Isn't Um we do have to most of us have you know family obligations of some kind or you know financial obligations one way or another It's a you know mortgage or a car payment or whatever like money is an issue But what that question does is help you as a man get to the heart of the matter of what am what do I actually care about Like

Jake Kennington 33:59

Mm-hmm

Don Ross 34:00

it's it's more of a legacy question you know like

Jake Kennington 34:02

Mm-hmm

Don Ross 34:02

kind of impact that I actually enjoy making on the world around me or on people or you know on business or whatever Uh and it it gets to the things of like where do I come alive You know where do I actually find joy Um and those are the places to start right Starting with the money issue is the wrong place to start And I think too it reveals that like Okay Uh maybe your passion is you know teaching or it's healthcare or it's you know I mean pick whatever from the list It's music or you know who knows what it is Um there may not be a readily available career path for you to jump straight into to be able to you know pursue that passion or that thing that you love But I like what you said about like Could you incorporate this into what you're currently doing Or you know on the side in some small way just to start experimenting with it see what aspects of it you actually do enjoy doing You know if if teaching is your thing like could you find a way to do some like seminars or workshops for your current company or you know like occasionally like on the side as a a digital sort of thing Like what are some ways that you could explore being able to do that and incorporate it into what you're doing and see if Hey does that open some doors Do you start building some relationships or some networking with other people who value you or see your skill in that area And would you know like to see you do more of it I mean there's there's all kinds of doors that can start to open up as you get started doing something right But if you're just looking for the one door that's Says here's your opportunity to replace all of your income and come do the thing that you love Like I think for most of us that door just doesn't exist Right It's it's not a thing that's never what transition is actually gonna look like even though we all would love it to it would be so nice if it did but it just doesn't So I I just think the the perspective that you're shedding there uh is is so incredibly Full It's so it sheds so much light onto hey there is a way to be able to do this Uh the path probably looks different than you imagined that it would but you can get there and you know here's a a really simple way to get started So man that's great I just the perspective I think is so helpful for us as guys So yeah

Jake Kennington 36:11

Yeah

Don Ross 36:12

Keep us going Like where did it go from there How did you now get to kind of the place of what you're doing with actively human and like um you know are you still doing engineering stuff at this point and like what is the you know next steps look like for you at this point You know where are you in the process

Jake Kennington 36:29

Yeah So one of the missing links for me uh that I kind of figured out along the way was this element of what I call connection Uh you guys used the word tribe right And and I love that Um so for me one of my projects that I had one of my four Ps was I wrote a children's book for my oldest son Um I've since self-published that it's on Amazon It's been an awesome experience I'm writing a second one for my second son because he's like dad where's my book Um and then I know and I've committed to do at least four Um and again this is why I love the mentality of kind of a project based you know approach

Don Ross 37:09

Yeah

Jake Kennington 37:09

don't have to put all my eggs in the basket of like I'm gonna be a children's book author from that Like this is my new identity It's just like I'm gonna try this and if I like it I'll do more of it And so um I I wrote this book but I originally just shared it with my wife and my son and and that was great And and we reconnected over over that experience But a few years went by and I had the itch to polish it up make it a little bit better um and put it out into the world Self-publish it put it on Amazon

Don Ross 37:40

Yeah

Jake Kennington 37:40

and I've since sold not millions of copies but hundreds

Don Ross 37:45

Yeah

Jake Kennington 37:45

connected with people that are thousands of miles away from me that have read the book and and shared it with their kid or their nephew or or things like that I've met so many people at conferences and other places where I've been able to donate and share This book and I've realized that there's kind of this pattern that I help people follow of create share and connect And that's exactly what you're doing with Manhood Tribes You you've made something of value something useful that can help other people You've shared it with those people You're trying to share it with those people as many as you can You're connecting much more deeply with them than you would have if you didn't do any of that Right And so I I figured that out through simply writing a children's book connecting with my own family and then having the wherewithal to shed my ego and be like I don't care if nobody buys this We're gonna put it out in the world See what happens We're gonna try right And if we fail we fail But that's okay And I've gotten to connect with with various people through that effort And so now I wrap that into my coaching again with Redefine success That's kind of the first part realign with what matters is like the actionable part Like how do you live your day-to-day life to take that next step to implement the four Ps and your projects and that kind of thing And then the reconnect at the tail end Who are you gonna share these things with You're you're not just supposed to as a human being like it doesn't really help you to become this awesome human and then keep it all to yourself

Don Ross 39:20

Right

Jake Kennington 39:21

right We all wanna work on ourselves We all wanna develop personally and become the best version of ourselves But the thing that I had that was that was missing that I didn't have Was this sharing this this this pouring out right This helping other people And so that's what led me to to really do coaching was to kind of connect these dots and be like how can I make the greatest impact Not because I'm important or I have something to offer but I have been blessed with a lot of uh skills and experience and other things that I wanna pay forward To kind of the younger generation or or the the next generation And so again it's kind of what can I create How can I share that And then what connections can I make so that that's kind of the framework And then with the business actively human that it's been one-on-one For the last two years I've only done one-on-one coaching um almost exclusively I've done a handful of group Programs or group events but they've been kind of one-offs My plan is to wrap up 2025 finish one-on-one coaching and do a a a group program kind of an an accelerator of sorts and I'm really kind of bummed to lose the one-on-one because there's something about the vulnerability that happens Just talking to one person one-on-one

Don Ross 40:36

Yeah

Jake Kennington 40:36

And the deep connection But I'm also super excited for the the group aspect of Actively human because there's just a synergy that comes in the group with with allowing other people to also share their experience and and help one another and do that in a group setting So I'm really excited 2026 we're gonna launch a group program and looking looking excited and and forward to that

Don Ross 40:59

Yeah that's fantastic This has been an incredible conversation and I think super helpful full of wisdom Um if some guys are watching Or listening and they're going man I'm at that place of like I'm feeling a little bit uh discontent or I've just kind of got the itch you know of maybe wanting to do something different and they're listening to you and thinking that guy could maybe really help me figure out how to chart a course for myself What what's the best way to be able to get in touch with you and and what can they uh look towards in terms of um working with you

Jake Kennington 41:30

Yeah I I'd love to uh chat with anybody My website is actively human.com Pretty simple Um I'm on LinkedIn as well You can look at me Jake Kennington um pretty you know you'll see actively human everywhere on there and I'd love love to EE either of those avenues but I also have a free resource for anyone listening that like you said is anything that's resonated or if they they see themselves and what's being said or or they go man that's me right now And I I could use some help Um I have a free resource Um I call it the Own Your Life Playbook Um we talked about roadmaps and playbooks and things like that This isn't necessarily like here's the next five years of what you can do But it does give you it does give you a few three practical Tangible next steps of how you could just own your life be energized for work and excited to come home every day And so again that's the own Your Life Playbook If you go to actively human.com/hashtag playbook you can get that there It's free I'll just ask for your name and your email so we can connect But again actively human.com/hashtag playbook You can get that free resource and I'd love to chat later down the road

Don Ross 42:42

Awesome Uh we will put the link to that as well in the show notes so you guys can look for it there We're also gonna have uh a link to it in our weekly email newsletter So if you're not already a part of the Manhood Tribes newsletter now is the time to sign up for that You can go to Manhood Tribes Dot com Uh and right there on the homepage you can join the newsletter and be able to get updates on everything that we're doing and talking about at Manhood Tribes Um but Jake this has been really really great Thank you for taking some time with me today and with our watchers and listeners um to be able to give them some great wisdom on all of this about how to handle our careers I know it's something we're all uh as men trying to figure out Well so thank you

Jake Kennington 43:20

Thanks for having me Donna I appreciate you having me on the show and and we've become good friends I've read your book um love what you're doing with Manhood Tribes and keep going man Keep at it This is fantastic

Don Ross 43:30

That's great Thank Thanks Jake I

Jake Kennington 43:33

Thanks We'll see you