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Mar 28, 2018

In this episode, we delve into lifelong learning – the key to growing your superpowers, whether you’re interested in taking the next step in your career or feeding your side hustle. We gathered expert tips and advice on how to keep learning and how to decide what new skills will most benefit you. We also get the scoop on how to get the most out of learning conferences and what it takes to earn a certification from Microsoft.


Listen to this episode for a chance to win a free three-month subscription to LinkedIn Learning! One lucky Windows Insider will be selected to access the entire LinkedIn Learning library of 10,000 courses. To enter, tweet about the new talents and knowledge you’ve gained through LinkedIn Learning, and we’ll randomly select one entrant to win. So, let us know on Twitter how you’ve used LinkedIn Learning to up your game. Then, tag your Tweet with #alwaysbelearning and #windowsinsider to be entered into the drawing. Entries must be received by Wednesday, April 18.


Episode transcript

JASON HOWARD:  Welcome to the Windows Insider Podcast.  You're listening to Episode 13.  I'm your host, Jason Howard.

Today, we're talking lifelong learning, that is, how to continue growing your superpowers, whether you're interested in taking the next step in your career, feeding your side hustle, or an amazing new hobby. 

Plus, we'll share our Windows Insiders can access exclusive free courses on LinkedIn Learning. 

Our first guest is "the" ultimate lifelong learner.  She took a break from her busy job at LinkedIn to share pro tips for acquiring at least three new skills every year. 

SAVANNAH BARRY:  I'm Savannah Barry, and I am a marketing manager at LinkedIn, and I work primarily on LinkedIn Learning. 

JASON HOWARD:  Awesome.  Welcome to the studio. 

SAVANNAH BARRY:  Thank you.  Thank you for having me. 

JASON HOWARD:  So, we've heard from our colleagues at LinkedIn that you are "the" ultimate lifelong learner and are really savvy in terms of being able to work on new skills to grow your career.  Would you mind sharing with everybody your method for doing this?  

SAVANNAH BARRY:  Yeah, totally.  So, I'm just a curious person in general.  If there is a problem that I come across, I'm very eager to learn how to fix it.  I have a hard time, like, just kind of stepping back and saying, "Like, okay, like, someone else handle this problem."  Which I think has driven me to be naturally a very curious learner, and kind of have a desire to learn a lot.

So when I first joined, I actually joined the team prior to LinkedIn acquiring, and I worked on our enterprise marketing team there.  And a great example about what I did there was we needed some e-mails to be coded, and we had to basically rely on an engineering team to build them.  And I was, like, "This is not efficient, I cannot get stuff done in the timely manner that I would like it to be." 

So I basically taught myself how to code e-mails, which I had no idea how to do.  But I had a need.  I had a problem I needed to overcome, I had some campaigns I wanted to ship, and yeah, I spent months after work learning HTML, taking courses on Lynda, LinkedIn Learning, reading books -- just like basically picking my fiancée's brain, like, "Please teach me how to do this."  And at the end of the day, you know, I think it, in general, has made me a better marketer.  That's a great example of just like one very tactical thing I did.

But I reserve an hour out of my week, every single week, to learn.  Truly, I have a calendar invite on Friday, it actually will be after this podcast, where I will basically just reserve at least an hour just to sit down and read something that's like relatable to my career, watch an online course, listen to a podcast -- really, anything that can kind of help me achieve my goals, which I think that has been on my calendar as long as I can remember, so that's kind of how I can carve out time.

JASON HOWARD:  Well, it sounds like you have a bit of a system -- almost like you've planned out time to go and learn new things.  Can you describe some of the, like, the mindset and the process you have behind that? 

SAVANNAH BARRY:  Yeah.  I think just knowing that you need to make the time, like, kind of just clearing things out of your brain, off of your desk. 

I actually go to like a different place.  I'll go to a coffee shop, I'll go to a different room in my house, just kind of find a place where I feel a little bit inspired, just to really sit down and focus on the task at hand. 

So, for example, right now, I'm learning UX design.  So I got a bunch of books.  And this all stemmed because I was using an app and I was, like, getting really frustrated at it.  And I was, like, "Why am I getting so frustrated at this app?"  And there's such a psychology behind how we, like, interact with things.  And I was very keen to understand. 

So that is currently what I'm doing.  And I have a book in my car that I will be diving into when I get done here, and probably go into a coffee shop or something and read. 

JASON HOWARD:  So one of the things that I was kind of told on the side is that you have a vision board, right?  And you list personal and professional skills --


JASON HOWARD:  -- that you want to learn.  What prompted that?  Where did that come from?  I don't have a whiteboard at home, so -- I mean, you know, you might inspire me to go out to Staples or something and go get a whiteboard this afternoon. 

SAVANNAH BARRY:  Yes.  I personally think that everyone needs vision boards.  I try to make my family and friends make vision boards with me.  It hasn't really caught on with them as much as it's caught on with me.  (Laughter.)

But this year, I actually did it on a whiteboard, and I like drew out what I wanted to do. 

So I draw, like, pictures and goals and just what I want my year to look like.  And that always consists of three professional and three personal things I want to learn. 

So where did it start?  I think I was like in college and one of my psychology classes, like, talking about vision boards or something -- I don't know.  I don't even remember where -- exactly where it started, but I've been doing it since I was in college.  I used to make my roommates in college do it with me and cut out pictures from magazines and glue them on paper. 

We'd go get the hot pink, big poster boards --

JASON HOWARD:  Oh, goodness, yeah. 

SAVANNAH BARRY:  -- and like glue stuff on there.  Yeah, I did that. 

JASON HOWARD:  It's almost like a high school collage.

SAVANNAH BARRY:  Yeah.  But then when I joined LinkedIn, we have these things called "in days" where we have basically one day out of a month where we focus on doing something outside of your job. 

So every January, it's like a vision "in day."  So they actually encourage you to make mood boards.  Like, okay, perfect.  (Laughter.)

So started doing it at work and now I work at home, so now I have a little bit of a different vision board area, but yeah, it's truly pictures, words, things that just inspire me and kind of keep me motivated throughout the day, throughout the year, and just a way to kind of keep myself accountable for the goals I set early on in the year and just really make sure that those are staying top of mind for me throughout the day. 

JASON HOWARD:  Was this something that you did individually?  Did your team come together and you kind of like group -- encouraged each other?  Like, what was that process like? 

SAVANNAH BARRY:  Yeah, it was a little bit individual, but I definitely tried to source feedback from, like, my manager, my peers, like, here's kind of what I'm doing, do you have any ideas on, like, professional goals that I should maybe focus on for next year? 

This year, one of my learning goals is SEO and SEM, which I haven't really gotten my feet wet with yet, but my manager was basically, like, "Hey, here's something that would be pretty interesting I think for you to learn."  And so that's another thing that I'll be focusing on. 

JASON HOWARD:  I'm assuming SEO being search engine optimization? 

SAVANNAH BARRY:  Yes.  Yes.  Yes. 


SAVANNAH BARRY:  Thank you for clarifying.  (Laughter.)

JASON HOWARD:  No, hey, I mean, you know, this is my Microsoft, we use acronyms like they're going out of style.  (Laughter.)

So can you tell me a little bit about, like, your decision-making process?  You said in this circumstance, you know, your manager, you know, you sought some feedback to help you guide down that path, right?  And, obviously, there's things that you come up with on your own that you want to learn.  So how do you decide what's going to be the best use of your time?  Because, I mean, that's kind of the limiting or deciding factor here is you have to make the time to do it, so where does that decision process come from?

SAVANNAH BARRY:  Yeah, you know, I really try to focus on things that I think will help me become the professional that I want to be, and really the person that I want to be.  I think about, "Where do I want to be in five years, and like, what skills will help me get there?" 

So I do a lot of research.  I read a lot of blogs, I do a lot of peer research, asking around, like, people who are in jobs that maybe I aspire to be in, like, what are some skills that they think helped shape their career, take them to the next level? 

And I usually start with a pretty long list.  I'll, like, throughout the year, I'll have, like, a running Word doc and I'll just put stuff in there, and then I can reevaluate and say, "Okay, here are the things that actually feel tactical for the year."  The UX one was definitely not on my list, it just like -- my, like, obsession with, like, how I'm interacting with things, I was, like, I need to.  This is a learning thing that I need to do, and I do think it'll make me a better marketer at the end of the day.  So that was an off-the-cuff add to the list. 

JASON HOWARD:  Wait, so when you look at the concept of lifelong learning, on the surface, it seems like this great goal, everybody should be doing it, but given, you know, we mentioned time a minute ago, some of the listeners are going to sit back and say, "Hey, you know what?  I'm crazy busy, I have laundry to do, I've got work, I've got kids, I've got family, I've got to feed the dog."  Right?  You know, I had to get up at 6:00 in the morning, it feels like I don't get to sit down until 10:00, 11:00 at night.  And it was never my time for me to invest in myself.

So how do you stay motivated to make that time?  How do you drive yourself to make sure that you put it on the list of things that you absolutely have to do? 

SAVANNAH BARRY:  Totally.  I think that everyone is very busy, and I think that's, like, in general, a big blocker to learning for people.  I've just found ways that it organically works in my life. 

So I listen to podcasts a lot.  I'll find relevant podcasts that are aligned to something that I'm currently learning.  And maybe that week I can only listen to a podcast while I'm walking my dog.  Like, that's all I can do.  And that's okay.  Every action you take and every step that you take I think is part of your learning journey, and not everyone has an hour a week to carve out for learning, and that's okay. 

If it's bi-weekly, if it's once a month doing two hours a day, I think that, in general, if you need your support of your friends and family and managers, like, it's fun to make it a little bit more of a collaborative experience.  Like, "Hey, guys, I want to make time for learning, you guys should, too."  And I think that also helps create a little bit more accountability, and also maybe frees up some time for you, if everyone around you knows that it's a priority. 

JASON HOWARD:  So how has learning helped you professionally? 

SAVANNAH BARRY:  Well, in general, I think -- I've gotten a couple promotions within my role just specifically because I've been able to go above and beyond of what my normal job consists of.  I think it -- in general, it's made me a great cross-functional partner. 

I mean, a lot of the work that I do in marketing, and I'm sure a lot of other marketers out there, is very cross-functional.  You're working with a ton of different people, a ton of different teams, and I think my desire to understand HTML, desire to understand SQL, desire to, like, understand some of these things that maybe I'm not using a ton, but other people are, has really helped me to be a more empathetic partner, to be a more constructive feedback-giver, it's just really helped me a lot in, like, developing really strong relationships.

So I feel really lucky that I actually work on a learning product, it's kind of crazy, it's truly the perfect job, I love it. 

But, yeah, I think it's just that curiosity and that desire to always want to be doing more and really just -- that curious mind.  And I think it has helped me in my career, and it's allowed me to start doing like more of a different marketing role.  And I was, like, "Ooh!  This marketing role looks interesting." 

And so I started learning and developing and asking people who did that job, like, "What does your day-to-day look like?"  And I was able to move into that role with not having the total skillset that I needed to have, but I think my managers felt confident that I knew what I was doing, and I could handle it.  And if I couldn't handle it, I would learn how to do it.  (Laughter.) 

JASON HOWARD:  So one important question that I want other ask you is:  How do you inspire somebody else to learn?  Through the conversation that we've had, it seems a big piece of it is you have to have some of this natural desire, right?  If you're not the curious type, it sounds like it could be much more difficult to kind of get personally inspired.  It's almost like you need to look externally for some of that motivation. 

You mentioned mentoring.  That's one of the things that's really important here at Microsoft is the concept of having a mentor, finding somebody who's in a space, hopefully outside of what you're doing, because at least within this company, there's a lot of leaning on your team, leaning on your peers, like partner teams, and you kind of naturally build up some of that learning along the way as you work with other people, but having somebody outside of the circle of which you normally focus on, they can give you a much different perspective. 

You know, obviously, this is a bit work focused, but they can give you a much different perspective than the way that you are accustomed to looking at things. 

SAVANNAH BARRY:  I 100 percent agree.  I think something that's been really valuable for me is having those mentors who can help me look at what is outside of my narrow range of focus.  And as a mentor, that's something that I strive to do, too, is say, "Hey, like, what do you want to do?  What do you want to learn?  What do you want to be, you know, five year -- two years, next month?  What do you want to be doing day to day?"  And if that doesn't align with what you're doing now, then how can we really set you up for success to be where you want to be?  What are those skills you need to learn to get that promotion?  What are those skills you need to make a horizontal move? 

And I think learning can be tied to your professional goals.  And I think so often we lose sight of what those goals are.  I mean, everyone is busy.  Work is crazy, personal lives are crazy, your kids are running all over the house.  Like, things are crazy.  But I think if you keep in mind those goals and talk to someone, find someone in a different organization or different company, reach out to someone on LinkedIn and just say, "Hey, I like what you're doing." 

I find myself reaching out to a lot of people on LinkedIn to just say, "Hey, I saw this blog post, would love to know how you went from this job to this job.  Do you have five minutes?" 

I just had coffee last night with a friend who reached out to me because he wanted to learn more about what I'm doing professionally.  Like, he wants to make a career change.  And he's, like, "Hey, tell me about some of the skills you acquired to be able to do that.  Help me out.” 

So I think just learning on other people and keeping true to your goals and keeping true to who you are, that's really what motivates me. 

JASON HOWARD:  Do you have any suggestions on getting people started? 

SAVANNAH BARRY:  Yeah, I mean, it depends on what you're trying to learn.  I rely on our LinkedIn Learning, like our own product a lot when I'm thing to learn more of, like, the technical skills that I want for my professional career. 

An example, we have instructional designers on our team who basically build out this learning path, and it basically takes you through nine hours of learning, which is a lot, and not everyone has that -- like, it's a collection of courses that it shows you and tells you, "Hey, here's what to expect.  Here's what you're going to be learning."  You can kind of see the courses that you're going to be taking.  And you can say, "Okay, this is a very easy way for me to get started."  I mean, that's what I started doing for UX, I'm deciding to read this book in parallel.  That's what I'll be doing for SEO.  We have a learning path on LinkedIn learning that I'll be using.  That's what I did for HTML, it's what I did for SQL.

So I think there's people who have done a lot of the legwork for you, and I think just finding a resource that aligns with what you're trying to achieve. 

So figure out that skill.  What are some of the most in-demand skills?  What's going to take you to that next level?  And then find out where you can learn it.  Learning paths are a really, really great, easy way to absorb information, and it's a lot of information.  When I first looked at it, I was like, "Okay, ten hours, wow.  Okay." 

But when you actually think about it, that's the whole learning journey right there, that's it all.  Right there, in front of your face, you can look at it on your phone, I listen to just the audio sometimes if it's like more of a soft skill.  There's lots of ways to really engage with learning. 

JASON HOWARD:  Well, before we wrap up here.  Any final words of advice or life tidbits or any other awesome vision board things you want to share with the listeners? 

SAVANNAH BARRY:  Oh, gosh.  Life tidbits?  I mean, I would just always stay curious, always ask questions, and just keep learning, and have fun while doing it.  I just urge everyone to stay curious. 

JASON HOWARD:  Awesome.  Thanks, Savannah.  Thank you so much for your time today.

SAVANNAH BARRY:  Thank you. 

JASON HOWARD:  Appreciate you being here.  Hopefully, the listeners have enjoyed this as much as I have. 

SAVANNAH BARRY:  Yes, me too.  Thank you. 



JASON HOWARD:  For tech professionals, keeping up with the latest knowledge is everything.  Have you ever wanted to know if becoming a Microsoft Certified Solutions Expert would be worthwhile?  What about how to tackle the amazing and sometimes overwhelming options to learn at Microsoft Ignite? 

We talk shop with our next guest, Aaron Buckley, a Windows Insider and IT pro at the company Alex and Ani based in Rhode Island.  Good morning, Aaron, welcome to the Windows Insider Podcast.

AARON BUCKLEY:  Good morning. 

JASON HOWARD:  So, tell us about your career as an IT pro.

AARON BUCKLEY:  Yeah, sure.  I got my start in IT working at my college help desk.  That evolved into my actual career path.  Even though I was not studying IT in academia.  And so now at my current company, Alex and Ani, I kind of jokingly refer to myself as an "army of one," particularly with client management and devices. 

I am running our Intune mobile device management, I am also architecting and governing System Center Configuration Manager, and I am in charge of leading the charge for Windows 10.  We're upgrading from a bunch of 7 and 8.1 machines. 

JASON HOWARD:  That is definitely an interesting career path.  I've got to tell you, you said that you didn't go study IT in college.  I'm actually in that same boat, right?  It's something that I haven't talked about on any of the podcasts before, but I was fortunate enough to go to university, and my degree is in economics.  Right?  And here I am working at --

AARON BUCKLEY:  Economics? 

JASON HOWARD:  Yeah.  And here I am working at Microsoft, right?  Trust me, I did not see that one coming. 

AARON BUCKLEY:  I might be able to beat you in terms of relevance.  My degree -- I got a double bachelor's degree in psychology and in political science.  (Laughter.)

JASON HOWARD:  All right. 

AARON BUCKLEY:  So I'm not sure how I got to IT.

JASON HOWARD:  You took a left turn at Missoula, man. 

AARON BUCKLEY:  It's a passion.  (Laughter.)  Yeah.  I should say, you know, while I had my interest in academia, I've always been an enthusiast for technology.  And so I actually consider myself really, really lucky that as my career, I'm doing what I love.  And I know that that's kind of aspirational for a lot of people.  I somehow achieved this, I'm really proud. 

JASON HOWARD:  So I have had the pleasure of speaking with you before.  We actually met at Ignite last year at the Windows Insider booth.  We had several Insider roundtables, met you there, learned a little bit about you there and obviously, you know, happy to have you back and actually get to talk to you on a more one-to-one type basis here.

Through some of that conversation, you know, found out that you're a Microsoft Certified Solutions Expert.  Side note for our audience.  You may be asking yourself, "What is a Microsoft Certified Solutions Expert, or MCSE?" 

These are folks who have achieved a Microsoft certification that validates they have the skills needed in a particular area -- for example, app development or cloud infrastructure. 

Aaron, can you tell us why tackling the certification was important for your career?

AARON BUCKLEY:  That's a good question because I've got to tell you, some of these exams, I think they were actually tougher than writing some of my 25- or 30-page term papers.  (Laughter.)

For the first couple years of my post-college, entry-level workforce, I was at the help desk level.  And through just demonstrating my technical competency, I got to be a level-three help desk, or escalation technician. 

But it was really at the point where -- I remember the conversation.  I went to my boss and I didn't throw it down, but I handed him my certification saying that, "Wow, yeah, I really am an MCSE."  And it was actually a couple weeks after that that I got my first post-help-desk promotion.  And at that point I joined my company's system engineering team. 

And that stuck out to me because I wouldn't tell people that you have to have a certification in order to jump to higher levels in your technical career path, but it was a milestone and a marker that I was able to hand my leadership, and they were able to say, "Wow, you not only have you demonstrated to us that you know this information, but you somehow convinced Microsoft that you know that technology."  (Laughter.)

And so that, I think, was really important.  That was fundamental.  I'm going to admit that I definitely failed my last MCSE exam three times before I finally nailed it on the fourth attempt.  And let me tell you, when I walked outside having finally passed my certification, I screamed at the sky I was so happy.  (Laughter.)  I mean it when I say that I think these MCSEs gave me more of a challenge that some of my college courses and final exams.  You guys are not messing around.

JASON HOWARD:  So, no doubt, you've obviously gained a lot through this process personally, and of course it's impacted you professionally.  So kind of on a broader scale, for others out there who may be considering something like this, what is some of the extra value you see in getting this type of certification?  How would you apply it more broadly? 

AARON BUCKLEY:  Jumping to college for a second, a lot of times people emphasize at the point of going through, like, structured college courses is to really build up someone's critical thinking skills and the way that they approach problems. 

I would apply that same sort of ethos to the certification process.  I think that the way that I approach confounds now in my system or broadly in IT is strengthened by some of the problem-solving processes I picked up through the certification process.  Not just the particulars of my certification path, like, "Oh, of course, that's where you go in the SCCM console for that."  But also just advancing my core understanding of basic troubleshooting steps.  Like there's an awareness of knowledge that you get going through these certification processes that I think really just levels up someone's engineering perspective, or their troubleshooting perspective.

I'm trying to think of the right way to describe this.  It's almost like a refining of the way that I approach problem-solving.  Does that make sense? 

JASON HOWARD:  Yeah, absolutely.  If I'm interpreting some of what you said correctly, it's -- part of it is learning the actual materials that you're reading through, right?  Some of it's going to be new stuff, you'll pick it up along the way, you'll get a chance to, you know, take a preview build and go tinker around and see how it works and see how it functions.  But on top of actually covering just the specific materials, it's changing the way you think about what you do already and you've found some ways to kind of tweak and enhance and gives you new products in just some of your day-to-day type activities. 

AARON BUCKLEY:  Absolutely.  And I think that's something that Microsoft in the certification process does really well, and I think it's part of Microsoft's intent.  As you're going through these certifications, they're updated constantly, like, I think yearly.  Like, the questions you're asked, the technologies you're asked about.  And I can definitely say that the actual certification and testing process has made available to me the various ways that I can solve particular problems. 

Like, for example, there have been a couple of times where, after going through my Windows 8 MCSA, I realized that there were so many things I was doing wrong, or just not doing the best way with even just customizing a Windows image. 

And then I take some of that that I've learned and I'm, you know, using PowerShell to strip out -- sorry Microsoft -- the default Modern applications that are in your corporate image.  Maybe my users don't need Candy Crush pre-installed.

But even then, like, a recent example would be a problem that I have at my company is that we have a bunch of iOS devices that I have governed through SCCM and Intune, sort of your hybrid solution.  And we've run into some issues because iOS devices, we have no way to govern updates for them, and that's important because my company has a number of line-of-business apps that are made for certain versions of IOS. 

Testing might not be fully complete for updating that app to the next version of iOS.  Well, I mean, it turns out that I learned in some of my recent certifications that testing that Intune standalone, Intune based in the Azure portal does have these iOS update policies.  So now that has directly informed me for the next six months or so that I have some architectural changes I'm going to be making to my device management and governance structure. 

And that's something that I probably wouldn't have known right off the bat unless it was being made available to me through this process.  Just one example. 

JASON HOWARD:  That's awesome. 

AARON BUCKLEY:  Really helpful, actually.  (Laughter.) 

JASON HOWARD:  So I'm going to shift gears on you a little bit here.  On top of just certifications and things of that nature, obviously Microsoft has many events throughout the year.  Right?  We have Build, we have Ignite.  I mentioned at the beginning of the show, you know, I actually had met you I person last year at Ignite.  What do you think about these types of events?  For somebody who hasn't been to Ignite before, say they're presented with the opportunity this year, right?  Do you have any, like, extra tips for them to try to get the most out of the experience? 

AARON BUCKLEY:  I have been privileged enough, and really it is a privilege to have been able to attend two Microsoft Ignite conferences.  Certainly, I'm really hoping my company would send me for a third time this year.  And that is because of how much I've learned. 

Ignite isn't a vacation, it's definitely a working trip.  And my first trip to Ignite, I would look around and see everyone, you know, sitting on couches on their computers.  And I'm, like, "What are you guys doing?  There are so many trainings to do, and there's this event!"  (Laughter.)  No, no, no, they had the right idea, I understand why they are taking things they're learning from these hands-on opportunities and starting right away in their environments. 

I would recommend that people go through the actual schedule, it's up a month or so before the actual conference.  Go through, pick out a good five or six knowledge areas that you are executing against in your company.  Pick those areas and go through and add them all to your scheduler.  I understand that at the end of that process, you are going to probably be triple or quadruple booked at probably every time slot available, but what I've found is that instead of trying to really structure my itinerary to Ignite, layer it all on and pretend you're Hermione Granger with the Time Turner and that you're going to attend them all because I've found that, you know, Microsoft does all of us a really great service by recording all these workshops. 

You're going to be able to attend one per time slot, you know, in person.  Go to the one that you think that if you had the opportunity, you would like to talk to the people hosting those particular workshops.  The other ones, if they're just technical deep dives or maybe introducing new technology, keep it on your schedule, but definitely be sure to go back on your own time after the crunch of the conference week is over, look through all those videos and actually catch up. Thank you, Microsoft, for providing this as a service. 

If you can't attend Ignite, I find that a lot of those videos also find their way to the Microsoft Mechanics site, also Microsoft Virtual Academy.  And so all of that is available to you. 

I would also recommend that even if you've layered up your schedule, it can feel intimidating.  Your phone's buzzing a lot with alerts for all these workshops and such.  Be sure to actually allow yourself some down time, because it's not going to be helpful to you to be sitting through five straight hours of workshops and then you sit down at the end of the day, and you're trying to remember this massive information dump that you sat through.  No, it's okay to actually skip a session here or there, some are on repeat later on in the week. 

I mean, it probably sounds a little cliché, but take care of yourself.  Give yourself time to sit down at lunch, absorb the morning, and prepare yourself for the next round of workshops later on in the day. That's something that I did not do my first year, and I came back thinking that I somehow needed to, in a panic, restructure all of the systems in my company.  There was this crazy anxiety that came from feeling so -- again, I said this word like three times, but so "empowered" by the experience at Ignite. That's some quick survival advice I'd give. 

Oh, and there's coffee everywhere, drink all the coffee.  (Laughter.) 

JASON HOWARD:  I don't drink coffee, but Mountain Dew, especially Diet Mountain Dew, is my best friend.  Caffeine is a wonderful thing.  (Laughter.) 

So kind of on a personal level for a moment, for you as an individual, what drives you to keep learning? 

AARON BUCKLEY:  I'm constantly refining my processes.  And as I gained more information, primarily from Ignite and these training videos, I am all the time sort of revising, refining, solving for efficiency, solving for capability -- all these things.  And I've found maybe a little too much of a technologist at this point, but I found that that perspective has been informing me in the broader and broader aspects of my life including, you know, going to the gym and working out and a more healthy lifestyle.  Even my personal finances and such. I've almost found that I'm taking this systems perspective and applying it to so many components of my life. I can't really help laugh at it sometimes, you know?  In a good way. 

JASON HOWARD:  Almost like the challenge of it is, in and of itself, a solid reward that keeps motivating you. 

AARON BUCKLEY:  Oh, without question.  I guess when I was growing up, I always had this fear of being stuck in a redundant, boring -- I've got to invoke, like, Office Space here, that sort of job situation.  And so working in IT where -- I mean, depending on where you work, every day is a whole, bright, new crisis to solve.  That's something I get a lot of personal and professional fulfillment out of. 

JASON HOWARD:  Yeah, I have to say, obviously being a different person, I take some of that same challenge, and that's part of what keeps me interested in my job is each day that I log into Twitter and I talk to some Insiders, see what they have to say, did they like the newest build?  What kind of crazy stuff did somebody find?  And unless it's a broad, widespread issue, every day that I log in, I either learn something new, I meet somebody new. 

AARON BUCKLEY:  Definitely. 

JASON HOWARD:  I have the chance to learn something about Microsoft technology that I never knew because it's not something I had ever touched before. 

I'm going to be writing a blog post here pretty soon on the topic of legacy filter drivers, and you know, some bugs that we worked through.  And it was before this bug came up, I honestly had never heard of it.  I had interacted with them before, right, as an end user, but it was one of those things that it was just part of the operating system, part of the software I was using, and at the same time, you don't know what you don't know. Until I was faced with the need to learn it, I didn't know it was something that I needed to go and learn about.  And now that I know more about it, it's fascinating. 

And I'm, like, "Oh, my goodness, there is a lot surrounding this."  And it's amazing how -- without getting too deep into the technology side of it -- one little change can have some really big outcomes, whether those changes are expected, and sometimes unexpected.  But the learning aspect of it is one of the key factors for me that keeps me really excited about my job because every time I get asked a question about something that I don't know about, it means that I have to go learn something. 

AARON BUCKLEY:  It's a whole new rabbit hole.  (Laughter.) 

JASON HOWARD:  Yeah.  What's something you, individually, are learning right now?

AARON BUCKLEY:  So, cars.  I come from a working-class family.  I have a couple uncles, a cousin, a grandfather who are all car mechanics.  And so I'm a computer engineer, I eventually got so aggravated -- not on my current car, I love my car -- but an older car.  The "check engine" light was constantly always on.  And that is horrible for a computer technician.  It's, like, "Oh, my God, there's an error message.  There's an error code.  I must fix." 

Instead of putting black electrical tape or something over the "check engine" light, I sort of started the conversations with my family of, "Okay, I need to replace this thing, Uncle.  I don't want you to do it, this is my car, I'm used to fixing machines, I am informed by my passion for computers and fixing those machines."

So it's really funny.  I then -- sort of applying that same ethos to learning how to fix my own car.  I can replace my tire, I even replaced my own brakes a couple weeks ago.  Kind of proud of that. 

JASON HOWARD:  Well, Aaron, it has been a pleasure chatting with you. 

AARON BUCKLEY:  Thank you so much for having me. 

JASON HOWARD:  Take care.  Cheers, man. 


JASON HOWARD:  By now, we hope you're inspired to grab lifelong learning by the horns and maybe even make a vision board or tackle a Microsoft certification. 

Our final guests are going to share a few more tips, and some exclusive resources available to Windows Insiders.  Here's Thomas Trombley, senior program manager here at Microsoft. 

THOMAS TROMBLEY:  You may have heard that Microsoft purchased LinkedIn, which purchased a few years ago. 

Now, LinkedIn Learning combines all the great content of -- that's more than 10,000 courses spanning business to tech skills and creative skills, with the personalization powered by LinkedIn. 

Here's a pro tip:  Windows Insiders get access to free LinkedIn Learning courses, and we'll let you know how to access those at the end of this podcast.  We'll also have a surprise giveaway.  Stay tuned for how to enter. 

JASON HOWARD:  Thomas is here with our second guest, Doug Winnie. 

DOUG WINNIE:  My name is Doug Winnie, I'm the chief evangelist and head of community for LinkedIn Learning. 

THOMAS TROMBLEY:  Some of our listeners may not know that LinkedIn is now in the Microsoft family.

DOUG WINNIE:  Uh-huh.  (Affirmative.)

THOMAS TROMBLEY:  What do you find most exciting about LinkedIn now being part of Microsoft? 

DOUG WINNIE:  It's interesting because the culture of the whole LinkedIn experience is still very much LinkedIn.


DOUG WINNIE:  But now we have the benefit of everything we have from Microsoft.  So I go to work, I go to a LinkedIn building, I'm able to exchange and do everything, just what we always did, so I don't feel that anything has changed, and everything's been going wonderfully.

THOMAS TROMBLEY:  Now, what is LinkedIn Learning versus the LinkedIn social network and platform that most people are familiar with?  And how do the two sort of play off one another?

DOUG WINNIE:  So your LinkedIn profile is essentially the front door for all your skills, your background, your experience, volunteer opportunities.  But LinkedIn Learning is able to tie in the skills that you currently have, job opportunities that you're looking to get, and can connect all the learning content that we have to the skills that you want to achieve a change in your career or to apply for another position. 


DOUG WINNIE:  Or to look at areas that you want to improve, to maybe do a career shift, or to maybe do a side hustle.

THOMAS TROMBLEY:  We're going to talk more on side hustling in a moment. 

DOUG WINNIE:  Awesome, okay. 

THOMAS TROMBLEY:  Online learning isn't just for students anymore, but people of all stages in their careers.  It just seems to have exploded in popularity.  Can you talk about some of the trends that you're seeing in technology and in the job market that are driving this wave of lifelong learning, especially through platforms like LinkedIn Learning?

DOUG WINNIE:  We have this model that we talk about inside of LinkedIn called The Four Squares.  The Four Squares involve major steps that you're taking over your evolution in your position. 

You first start off as, like, the eager beaver.  I'm ready, this is my first job, I'm really excited, and I'm going to nail it, okay? 

And then you get to this point where it's like -- not quite sure, maybe I bit off more than I can chew.  But then you start doing one thing.  You do one task, you get a little bit of confidence going into that.  And you're, like, "I got this, I can do this."  

Then you start doing meatier and larger projects, and you get to the mastery part.  Each one of these four squares represents a step on the journey that you're taking in your career.  Could be a career, could be a job, but it could also be something you're doing outside of your job like a side hustle or some sort of volunteer activity. 


DOUG WINNIE:  What's important, though, is as you're navigating from square to square, you need to find a new way to engage with your learning because you might have technical skills that you need to get from, say, eager beaver to, "Oh, my God, I'm not going to be able to do this."  To focusing not just on what you're doing, but how you're doing it.  To talk more about the interpersonal.  You might have some life situations that are coming into the workplace, things like that that are not the technical tactical things, but they help you kind of get through roadblocks or hurdles that you need to overcome in order to get your job done. 

What happens, though, is when you look at all these four squares, people think that they are in one of these squares at one time.  In reality, you actually are in all four at the same time.  Whether I'm in my career, I'm in my job, whether I'm a parent or a new parent, you know?  My baby's born, this is awesome!  And then you're, like, "I'm responsible for a child."  You know, this is hard. 

All these different things exist at the same time.  So if you look at it from that perspective, there's this constant cycle of needing to learn as you're going through this process. 

THOMAS TROMBLEY:  Kind of somewhat of a segue to this four-square approach, or this thought process, it kind of feels like a pendulum going back and forth. 

DOUG WINNIE:  Uh-huh.  (Affirmative.). 

THOMAS TROMBLEY:  And, eventually, you find your path as the pendulum kind of narrows towards the center. 

But I recently read a book by Angela Duckworth called Grit, I don't know if you've ever read it.  She shares stories about people striving to succeed, building perseverance and resilience into what she calls, well, "grit."  Doug, do you find it difficult or tough for folks to stick to classes on LinkedIn Learning, given how busy life can be?  Like, how do people have the grit to really see their learning through?

DOUG WINNIE:  Everyone has a different approach to what they need to learn.  So sometimes we'll have people that want to tackle a really long learning path, which is a sequence of courses that we've created that might map to a certification, like the Associate Android Developer Certification, which we recently partnered with Google on. 

Then we also have PMP certifications and other things that, you know, are very long-tail approaches.  But sometimes you need to just have that one thing that you need to get you through what you're troubled with today. 

And it's funny you talked about the grit.  We just launched a course with Sheryl Sandberg and Adam Grant on Option B


DOUG WINNIE:  Around resilience at work.  We just launched that this month.  And the nuggets that are inside of that, that if you just can watch one thing just to help you through a setback or a hurdle that you're having and to renew the positivity that's inside of you that you know is there, that's just being kind of --

THOMAS TROMBLEY:  Right.  Right.  Exactly. 

DOUG WINNIE:  -- pushed down, that can then propel you forward and then be able to go back onto your journey. 

THOMAS TROMBLEY:  And I think that offers some of the value proposition around online learning.  Like, there's this explosion of online learning opportunities that can kind of give you that "oomph" you need.  And I wonder if you could talk a little bit about how LinkedIn Learning's offerings different from, say, your competitors at, like, Treehouse, you've got Code Academy, there's Udemy, and the like. 

DOUG WINNIE:  I'd say the flexibility.  So just like I mentioned, if you want to go through a long path, you can do that.  If you want to just take one course to get you through a skill that you're trying to work on, or just that one video. 

The mobile applications that we have integration with LinkedIn, I mean, all of these things combined make it flexible for what you want to get out of it. 

A lot of times when I talk to someone that's really struggling with, "What do I need to know?  What do I need to learn?"  Sometimes, they focus on the skills, they focus on the technology.  "I need to do this, so I, therefore, need to know C#, I need to do all these programming languages and tactical things."


DOUG WINNIE:  And I say, "Lead with your feelings.  What do you want the emotional outcomes to be of what you're doing?"  And look at that as another way to approach your learning. 

Because the skills we have on LinkedIn and how you can build your profile is able to accommodate those more emotional social aspects of how you do your work, that creates a really unique way of building your learning journey on LinkedIn Learning as opposed to our competitors. 

THOMAS TROMBLEY:  That's really compelling.  I feel like you need to teach a course on just preparing to learn or an equivalent. 

DOUG WINNIE:  Getting into the mindset of your emotional learning journey.  Yes!  (Laughter.) 

THOMAS TROMBLEY:  I think a lot of professionals these days can identify with having a side hustle, as you mentioned earlier, or wanting to make a big shift in their careers.  Could you share with us a story about a LinkedIn learning participant you know or heard about that successfully fed their side hustle?

DOUG WINNIE:  There's one person, Sebastian Bleak, I read about his story recently.  And he recently had basically lost everything.  Lost his job, lost his home, everything, was basically living out of his car. 

And what turned into a career for him started off as just something very small, a little nugget. 

A friend of him said, "Just learn one thing, one thing every day.  It doesn't matter how small, doesn't matter how insignificant you think that it might be.  Just one thing."

So in his car, he was basically going through the library learning things like around illustration, graphic design, and through just chipping away at it one day at a time, he was able to get a job at an awesome graphic design company in LA, and he's now an instructor with us, actually, covering T-shirt design.

THOMAS TROMBLEY:  That's amazing. 

DOUG WINNIE:  But the thing is, if you think about it as just one little chip that you can do to this giant statue that you're trying to create, okay?  It can be overwhelming when you think about the vast amount of things you have to learn.  But if you just do it from a very agile approach and thinking about it as just, "What am I doing today to get there?" 


DOUG WINNIE:  I think that's something that's compelling about his story.

THOMAS TROMBLEY:  I feel like all too often we get so focused in our day to day -- like, I personally have a to-do list that's a mile long and I sat there and mapped it out in Excel and it said one day to complete all those tasks would take 25 hours per day.  (Laughter.)

DOUG WINNIE:  I have, you know, we talked about this before the show.  I've got some tattoos.  And I have one on my arm.  My husband, he always tells me, "Stop planning.  Stop planning everything.  You always are planning everything, why aren't you actually doing the things that you plan?" 

So I actually have that on my arm as a constant reminder to say it's not just about planning and creating to-do lists, it's about checking them off and having that sense of accomplishment at the end.  That's part of education, part of learning as well.  Don't get overwhelmed by the sheer vastness of what you have to learn.  What did I learn today?  And take pride in the fact that you learned that. 

THOMAS TROMBLEY:  Yeah, I remember my mom would always say life is what happens when you're busy making other plans. 

DOUG WINNIE:  Yes, that sounds familiar.  Sage advice.  (Laughter.) 

THOMAS TROMBLEY:  Tell me a little bit about how Windows Insiders can access LinkedIn Learning for free. 

DOUG WINNIE:  So, we've got some opportunities for the Windows Insiders to take courses on LinkedIn Learning.  And Insiders can stay tuned for the next Windows Insider newsletter to arrive in their e-mail.  And that will include codes to select free courses. 

And what we've done is every single month, we have courses from business, technology, and creative libraries, and we recently launched it so that people that are getting the German, French, Spanish, and Japanese editions of the newsletter get localized videos for those languages. 

The other thing is tying in with why we're all here in Redmond this week.  We have about 16 courses for our Microsoft MVPs that cover technology from all kinds of different topics -- business, creative, and technology -- and we're unlocking those courses along with the traditional four that we do every single month. 

So, that's great to see how we're taking the strength of the Microsoft leadership community and our community leaders and showing how they are able to give and provide their expertise on LinkedIn Learning. 


DOUG WINNIE:  So there also is going to be a Twitter contest that we're running.  And for --


DOUG WINNIE:  Ooh!  For those that are listening, we're doing a three-month subscription giveaway for LinkedIn Learning.  So if you win this, then you'll get access to LinkedIn Learning plus other LinkedIn career premium benefits to help you with your job hunt, you're looking at salary information or other aspects to basically boost your game on LinkedIn. 


DOUG WINNIE:  So what we ask you to do is tweet all the new talents and knowledge that you've gained through LinkedIn Learning and we'll randomly select someone to win. 

So to enter, you need to let us know on Twitter how you've used LinkedIn Learning, then tag your tweet with #AlwaysBeLearning and #WindowsInsider, and then we'll enter you into the drawing. 

And if you want more information about the contest instructions and rules, you can see that on the Windows Insider website. 

THOMAS TROMBLEY:  Let's talk a little bit more about how these folks could get started.  Do you have any tips for folks who want to get started with LinkedIn Learning, like, for anyone who might be feeling excited, but may be overwhelmed by having so much knowledge at their fingertips?  It can be a little daunting when you see the catalogue.

DOUG WINNIE:  It is.  One of the things that's unique is when you go to LinkedIn for the first time, you can identify key skills that you're looking to learn.  Based on that, it will then create and curate a selection of courses based on those. 

You can then go in and modify.  You can add one, you can remove one.  That will continue to kind of shape the recommended courses that are there.

The other idea is to look for a career or look for a job that you are looking to achieve and if you can do that, you can see on LinkedIn all the skills that are required to get that, and you can compare yourself to see, like, all right, how do I match up to that particular job? 

Then take those skills and feed them into LinkedIn Learning so you can build a list of courses there. 

The last one is to go through our learning paths.  They look daunting at first, but if you look at them from one step at a time, just like I said, one day learning one thing, you will get through and build the statue by chipping away at it one day at a time. 

There all kinds of learning paths based on business, creative, and technology careers and topics that are then segmented down into specific job roles or if you're a new manager or if you're entering into an executive or leadership position, there are all kinds of courses that we curate in learning paths to help you down that path. 

THOMAS TROMBLEY:  Let's talk about your own learning path.  We've talked about learn one thing every day, your arm says, "Stop planning."  You know, what are you learning these days?  Any secret things you're -- or hobbies or learnings that you're working on right now? 

DOUG WINNIE:  So when we talk about side hustles, for me, it's not necessarily a side hustle, it's just something that I love to do.  I love teaching.  And I've got my job at LinkedIn, which I love, but I really enjoy being in front of people and teaching and giving back all the skills that I have amassed in my career. 

So I've got 20 courses on LinkedIn around learning how to code and product management, I was a product manager for many, many years prior to coming to LinkedIn. 

But I wanted to make that different for me, so I became a teacher.  So I'm a part-time AP computer science teacher at a local high school in the Bay Area. 

The experience and the energy I get from that, but also the different challenges of looking at how do I approach a classroom is a learning opportunity for me.  And what's been fascinating is taking my product management skills where I look at things as agile, I put together roadmaps and I am constantly doing feedback from people on an engineering team or a design team and bringing that to the classroom.  Using a lot of the things that are on LinkedIn to help me with gathering data, to put together data visualization and to create a compelling story as to how the students in my class have ownership of the classroom and how I teach has been wonderful.  It's been fascinating because they feel, and they do, have ownership of how I teach.  What do I change?  Do I do more of this?  Do I do less of this?  Do I ditch my lecture notes and do slides instead?  And they're able to add and have ownership as to how they want to learn.

THOMAS TROMBLEY:  It sounds more collaborative.  Like, they have a stake in the game in some way and in that, there's a vested interest.

DOUG WINNIE:  And they know that I'm accountable to them.  When you think about a lot of teachers and a lot of classrooms sometimes that's not necessarily the case -- at least it was when I was a kid, where it was, you know, "I'm gonna teach this way, this is how it's going to happen." 

But when you take skills from other careers or other tracks and are able to kind of blend them together, that's where you're able to unlock about how you can change the way that you approach your career, and hopefully be a ripple effect to other people. 

THOMAS TROMBLEY:  That's inspiring.  I happen to know that you're a teacher.


THOMAS TROMBLEY:  I didn't know you were teaching high school kids part time.  I don't know how you can do that. 

DOUG WINNIE:  I'm also a part-time varsity lacrosse coach as well, so --

THOMAS TROMBLEY:  Okay, now I'm feeling lazy.  

DOUG WINNIE:  No, no, no.

THOMAS TROMBLEY:  All right, well, I discovered yesterday that you have a huge presence.  You're almost somewhat of an Internet teacher celebrity of sorts as a programming and technology-focused teacher. 


THOMAS TROMBLEY:  I saw you have a Computer Science Principles lab on C# with 100,000 views.  You have the Android App Development Quick Start, which I think you mentioned earlier, and that's got 300,000 views.  Programming Basics, half a million people -- Programming Basics, half a million views.  I even saw one on Windows Phone 8 development.  (Laughter.)  Which actually brought me over to Microsoft a little over five years ago. 

As a PM, I'm also looking forward to taking your Product Management Foundations course, it's been added to my list.  But what really got you interested in teaching technology? 

DOUG WINNIE:  When I was a product manager at Adobe, which if you go to my LinkedIn profile, you'll see very clearly listed there.  I managed a lot of the developer interactive products that we had. 

And I'm the kind of product manager that approaches everything with compassion for the user, understanding the problems that they're having, and good compassion for the struggles that they are experiencing with their products. 

I can approach that by improving the products, but I can also approach that by helping people learn how to use the products and the technologies that are there. 

So when I was a PM on the side, I did a series on programming and scripting with Adobe products.  And it was just something I liked to do, I wanted to help.  I wanted to share what I knew with other people. 

So I did that, and it was a big success.  And it led to a couple books, it led to some other teaching opportunities at places like San Francisco State and other places.  But I found that doing that gave me a new perspective in terms of how I could help people in a virtual way, because I always saw it as kind of a classroom thing where I had to be physically with them. 

Because of the power of the Internet and video and being able to connect with all these different people, gave me an audience that I never thought that I had. 

When I left Adobe and went to Lynda, I've now had even more people that I was able to really talk to.  And with LinkedIn, we have over half a billion members on LinkedIn. 


DOUG WINNIE:  When we think about the power that everyone individually has to write articles, to write short-form posts, or even with your phone, just record a video right with the LinkedIn app on your phone and just immediately put it up there to talk about something that you're going through today or a quick tip about how you were able to solve a problem yourself. 


DOUG WINNIE:  You can immediately learn and teach at the same time on LinkedIn.  That got me really excited. 

So I joined the content management team, trying to find awesome people to help add more of their experience onto the platform, and then eventually I wanted to connect all these communities together, which led me to my job today. 

THOMAS TROMBLEY:  That's a tremendous amount of value under that big umbrella that you described. 

DOUG WINNIE:  It's overwhelming sometimes.  But on the same note, I feel lucky to be able to have this opportunity. 

THOMAS TROMBLEY:  Doug Winnie, it's been really inspiring to speak with you today.  There's a sign that sits outside my office that says, "The only place that learning comes before knowing is in the dictionary."  And I feel like newly inspired to jump back on my own educational program.  And I hope some of our listeners do as well.  Thank you for your time today. 

DOUG WINNIE:  Thank you.  It's been wonderful being here and I'm thankful that I can be the drop to create the ripple effect. 

JASON HOWARD:  Thanks for listening to this episode of the Windows Insider Podcast.  Get the podcast automatically every month by subscribing on your favorite podcast app.  Until next time, Insiders. 

NARRATION:  The Windows Insider Podcast is produced by Microsoft Production Studios and the Windows Insider team, which includes Tyler Ahn -- that's me -- Michelle Paison, and Ande Harwood, and Kristie Wang. 

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Moral support and inspiration come from Ninja Cat, reminding us to have fun and pursue our passions.  Thanks, as always, to our program's co-founders, Dona Sarkar and Jeremiah Marble.

Join us next month for another fascinating discussion from the perspectives of Windows Insiders.