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Stride meets: Alexa Shoen



For our first episode of the Stride podcast, Sophie met with Alexa Shoen - a singer, tech thought leader, career coach and author. We’ve transcribed parts of our podcast for you below - if you’d like to listen as you read, click here.

Alexa's CV is really impressive - she's worked across Berlin, London and New York as a senior product strategist at Facebook, and in communications consultancy. She even got an exceptional talent visa for the tech industry, which the UK gives to just 200 people a year!


Alexa now has her own business helping others to build their careers, and has written a book setting out her 9-step method for getting the job you want. Entry Level Boss, is out May 14 2020 in the UK - we read a preview and really rate it!



Alexa, you run your own career coaching company, Entry Level Boss, and are about to release a book on your career coaching methodology. Can you tell us a little bit more about that?


Sure - so, the way that I started Entry Level Boss, which is the online career coaching education company that I founded a few years back, was quite simple. Many founders go through the process of founding a company because they're trying to solve their own problems. And that's exactly what I was trying to do. I could not get a job to save my life when I graduated from university.


Whenever I try to explain the problem that I'm solving to other people out in the world, I always say, “Okay, picture that you just graduated with a 2:2 in geography.”

“Great!”

“You didn't go to Oxford or Cambridge.”

“Oh.”

“Now what do you do?”

“I'd be a bit screwed.”

And I'm like, “exactly - these are the people that I'm trying to help.”


"The world is changing so quickly."

It is such a behemoth jump to get from academia into the working world. And you and I were chatting about this before we started recording, right? I realised that no one was serving that exact audience and there is actually a curriculum that should be being taught in career centers or by the NUS or something and, for some reason, because the world is changing so quickly with technology, everybody hasn't caught up yet. So, I thought I would step forward and say, I kind of have developed a little bit of a plan. If you want to follow me, I think I can help.


There's a thing that people say, about how this generation is so entitled. It wasn't that I was entitled, I just had been taught that I did all the right things.


I went to university, I got a Master's so I’m even more educated. Yes, it was in music, but still - right? And then all of a sudden, I show up on the front door of adulthood and I'm like, cool, where's my full time job? And it just wasn't there. So, I trial-and-error my way through what felt like the first three years of my career, maybe getting a 10-hours-a-week contract to do something or maybe a three-month maternity leave cover role, so on and so forth. And I had always been told it was going to be easy-ish, to get that first job because I was educated, and it just didn't wind up that way. So yes, Entry Level Boss was created based on all of my mistakes.


I love the optimism of all 25 year olds when they're in a situation that I guess a lot of us at Stride are in, where they're just like so fed up with the system, and you're like, “I have to do something!” It’s amazing that you've taken that feeling and turned it into something so productive.


Yeah, I mean, the thing that frustrated me so much is that this curriculum should exist. And the thing that made it so disheartening was just like how many grown-ups that were out in the world had forgotten how awful it was to go through this process. I had someone recently ask me why, why I'm the one who's qualified to give this advice, and I said, I don't know if it's that I'm qualified, but I've never forgotten how scary it is to try to start a career or make a career change. And I remember that fear from my own personal experience.


And how do you prioritise? With your singing career and entry level boss, how do you manage to balance having multiple passions?


"It's never as pretty as you think."

That’s a good question. I I think that so many people in our generation have these multiple passions. And I think the thing I would tell anybody is, it's never as pretty as you think that it is on the outside. And it's not like all these people have magically figured it out.


I think what I mean by that is, a lot of people see that I have a record on Spotify, and they assume that I have a label, and that the label paid for that to happen, and that if I'm doing any gigs, I have some publicists to booked me into it - and that somehow magically there's this this ecosystem that exists. When in reality, plenty of people that you see on the cover of Rolling Stone are still working like a part time job. The real secret of having multiple passions is just to realise that it's not pretty. But you do it anyway.


I loved the phrase that you mentioned in your book about career coaching, when done properly, being more like giving someone a fitness plan for them to follow. Would you be able to speak to that without giving away too much of the book?


So Entry Level Boss, the book and also the methodology that I teach people when I'm career coaching, is a nine-step process that we have formulated over the last few years about how to go through the job search effectively. I realised the one problem that people struggle with is not actually the big question of, “oh, what do I do with my life?”, and it's not “how do I format a CV?”


It's knowing what to do next, because you face rejection after rejection, or you get to a dead end, and then you kind of get stuck and you're not sure what to do next.


When you combine that with the fact that there are 20 million job postings on LinkedIn and who knows how many on Indeed, you get inundated with so much noise and don’t really have an idea of how to get through this process.


So, what we do in Entry Level Boss and the methodology that you learn in-depth inside the book, is literally just “do this thing today. Okay, now you've done this 45 minutes worth of homework I just assigned to you, so now we do this thing tomorrow,” and creating a framework for people to move through.


It’s as easy as going to the gym for your 8am class or knowing you're supposed to do five sets of 15 repetitions on a Tuesday night to get fit. It takes out that level of guesswork for people, because that is something that people really, really struggle with.


You can very easily get to information overload when you realise that one recruiter picked up your CV and passed it on to someone. Suddenly your inbox is full of absolute nonsense, but you have a feeling of pressure that should probably apply for some or all of it - it’s chaotic.


It is. I love to say that the internet broke the job search, because it really did. And for whoever is listening out there, if you think that it is hard to make a career move, it is not your fault.


Like, a cover letter, for example, always was a physical sheet of paper up until 20 years ago, that you would like to put on top of a CV and put into the mail. And those were the only two documents that anyone would ever know about you because they couldn't Google you - because who uses the internet, right?


And so we digitise this process, but now I have the ability to apply for 100 jobs a day. Or 200 if I'm really ambitious, right? If you, as a hiring manager, are getting 500 applications - how could we possibly function and find out who's the right person when there's so much noise and static, and chaos in the system?


I don't like to speak poorly of career centres at universities because I genuinely think that they're trying to keep up and do the right things. But, I think that the thing that I have said to many, many people who are older than me over the course of time is: you just don't know what it's like to look for a job after the recession unless you had to go through it yourself.


And yes, the economy's in a wildly different spot. It’s what, 10, 12 years on from the global financial crisis. But so many things changed between that inflection point and the internet becoming a default way of working. If you looked for a job in 1982, and now you've been in academia for 40 years coaching graduates on how to do their CV properly, I know that you're well intentioned, but you just haven't been through it, and you don't know how scary it is.


Absolutely - there’s a real need for people giving grounded careers advice.

Following on from that, what's your vision for Entry Level Boss in the next 5 or 10 years?


Oh, boy, good question. LinkedIn has a statistic right now that I'm obsessed with, which is the fact that today's graduates - class of 2020 - are going to have at least a dozen jobs before they turn 40.


And we know already that the career ladder is gone -now it's a career jungle gym or whatever other crap you've heard on some website somewhere. But, when you think about how many times this generation is going to be looking for new work, plus the fact that technical skill sets are changing - even if you know, Microsoft, five years from now, we might all be using a different type of word processing software - if you know a coding language, usually you're going to learn another one a year later.


Educated used to be this final state and then you would get on this career path. And now, it's going to be kind of a free-for-all of “how that hell will my career go in the way that I want it to” when you are not sure what that even means, because technology is evolving so rapidly.


There's no one on the side of the talent in this ecosystem, because recruiters want you to go and work for the companies that they work for, right? Or educators want you to go back and go to school and pay them more tuition money. And so we're kind of building this, I guess, GP for careers. That's that's the vision for what we're doing.


And I guess this is slightly a mean question, but what will it look like when you get there? Like, how will you know when you've arrived?


You know what, I've been thinking about this a lot recently. We have helped several hundred students - there are several thousand students who have read the Entry Level Boss newsletters since I started it with my silly emails when I was 25.


This book is coming out - or will be out by the time this interview comes out! My goal, or version of success that I'm trying to get to, is that we have a big enough brand presence where people know they have someplace to go for help, which seems kind of like a tricky thing to benchmark but I want to be in a situation where, when the next 23 year old gets stuck they don't feel like they're the only person in the world who's getting stuck. And also they know “Okay, I can't do this by myself, but I know who could come in help me and that is the team at entry level boss.”



And so now Entry Level Boss has really taken off, have you found your home or your niche now? Or are you still thinking that you might get back on the jungle gym?


Isn't it so funny how we all are obsessed with happy endings? So, I really specify a difference between happiness and contentment, not just in career stuff, but in love, in life, and health and whatever, right? We all are taught to be obsessed with happiness, which is a sense of euphoria.


What I'm much more obsessed with is the concept of contentment, and the way that I describe it in career terms is: I can't genuinely think of anything else I would rather be doing. I think that the vast majority of people are sitting in offices or on their shift at Tesco or whatever, daydreaming about all the things they'd rather be doing instead. I would love for everyone to get into a place like I am with Entry Level Boss.


I like that - contentment is definitely underrated. It's pragmatic.


"If you really are dreaming about it, break it down and tell me what the plan is."

Yeah, so many people have fantasies of the ‘dream job’. I think that it's great to have ambitions and I think that it's great to go towards something that you want, but I find that so many people don't actually get curious about what their dream job actually entails.


For example, I find it really interesting now that I'm a published author - or about to be a published author - how many people send me a DM on Instagram or whatever saying, ‘Hey, can you tell me how you got your publisher?’ or ‘Could you introduce me to your publisher?’


To me it's fascinating because, as a career coach, I teach people to break down what they want to do, step by step, and they are so obsessed with the idea of becoming an author that they haven't thought about the fact that the publishers that I work with only take submissions from agents. If you really are dreaming about it, break it down and tell me what the plan is.


In this country there’s so much pressure to choose your career path early on. There are patterns of choice-making: you're coming up to your GCSE's and told, "You've got to think about your options." A-levels? "You've got to think about options." The choices continue to narrow from there when you have to decide if you're going to go to university, to college, to do an apprenticeship or to start work.


How early do you think people should start thinking about how they will break down what they want to do? Is there a point where you think it's possible to say, I really love art, I really love maths, I really want to do something that combines these two - or do you think that it is better to kind of get your toe in the water and see what you enjoy on a daily basis?


I think that's a great question. And I think in the UK, especially with the pressure around whether you do A-levels or a technical qualification, it puts pressure on people even younger to try to start making these decisions. And so many people are not educated to do so.


And that's nobody's fault - it's just the world changing and all that. I wish that we didn't talk about it again, as if it was going to be this career that you're going to have for the next 40 years, because it's just not the way that the world is working anymore.


I think that we should be educating people, definitely at GCSE time, about what their plan will be. Ask, "what kind of thing would you want to spend the first half of your 20s doing?" That can make it a little bit less scary, because I think people shy away from making any decision if they think it's going to be permanent.


"Think about your strengths."

Facebook had this great definition that they teach to every employee on day one, about strengths and weaknesses and career stuff. In Facebook culture, what they mean by a strength is something that brings you energy - and a weakness is something that doesn't give you any energy.


So sometimes we have things that we're really good at, but you hate it. I think so many people are taught, well, you got good grades in this, so you have to keep going in this direction. Instead, the way that I have them think about their strengths :


  • What's something that brings you energy?

  • What's something that you do when you're procrastinating?

  • How could we put more of that into your actual career path?


For example, are you on YouTube tutorials about makeup all day long? Or are you obsessed with video games? Are you cooking in the kitchen? Or do you clean when you're stressed out? What are those natural things that you turn to when you're trying to avoid work?


That’s a great approach - it makes so much sense!



Have you seen a difference in how the process of approaching your first job is between male applicants and female applicants?


I think that all entry level people tend to feel a little bit screwed, and I've seen that across the entire gender spectrum. What I know is, we see the same thing to be true at the entry level that we do at higher levels: women want to really, really, really make sure that they are 100% qualified for a job before they apply. Whereas men have usually been conditioned to go for it, and hope that they can make something work.


A lot of the work that I do with women, in the first five years of their career especially, is about feeling you're ready for even that first job, instead of waiting for someone in the world to give them permission to move up a rank. Whereas men tend to catch on a little bit more quickly to the fact that they get to make the calls on how quickly they grow their career.


And what's the most valuable tip you have for someone who's navigating all this alone, without the benefit of a career coach, or someone giving them that validation or boost that allows them to take control of their career journey?


If people are really struggling, the number one thing that I can tell them is, studies have shown that 80% of jobs don't actually ever make it onto LinkedIn or Indeed, or any of the job posting boards that you're looking at, because they happen through personal networking and connections.


We could talk all day long about whether or not that's a good or a bad thing, but it is the reality of the situation. I find that many people hide behind their computers and want to stay safe, and their version of staying safe is to just send in online applications - and then wait and they wonder why nothing is happening. When in reality they're sending in 100 applications a week to this bottom-of-the-barrel 20% of jobs that are actually online. So networking is not an optional ‘nice to have’: it is the only way that you're going to find your way into the career that you want.


And finally, we've alluded to this, but when you started out, how did you define success? And how has that changed over time?


I don't think that I ever had success defined when I graduated from university, and certainly no one ever taught me how to define it. Actually, I think there could be entire curriculums that are yet to be created about how you actually come up with a plan for your life, and how you go out and hit those thresholds.


I was obsessed with the idea of getting to a place of safety early in my career. And I'm sure that's something I should talk about with therapists for the rest of my life, but my obsession was: how do I keep the same quality of life that my parents were able to give me and how do I make sure that the next time I go to look for a job, I have the safety of having already had a job on my resume - and that's a very real thing. I define it in the book as the ‘higher ability threshold’ because I just wanted to get to the other side where I could say, “ok, now I feel like a safe, grown-up adult.”


As far as how I define success these days. I think that I'm still trying to figure it out. But I am becoming a bigger and bigger believer in quantifying things. People constantly come to me and they say, “I just want a job that makes me happy.” And I say, “okay, what makes you happy?” And of course, people start crying whenever anyone is asked that. But it could be as simple as, “I want to take a job where my commute is less than 30 minutes,” or, “I want to take a job in the centre of Oxford because I hate going into London every day.” These quality of life things are just as important as what it says on your business card or profile. I don't think enough of us are encouraged to think holistically about the life that we want to lead: maybe you want to make this much money because you want to give back to charity, or you want to go somewhere particular on holiday someday. Those are all valid reasons to make career decisions. It's not just what you're passionate about.


Absolutely - taking a holistic approach to your career feels at odds with the linear progression that we’re encouraged to think about in school, especially with the process of progressively narrowing your options that we see throughout the British education system.


Did Alexa’s advice and experiences resonate with you, or spark any questions? Let us know!


You can contact us in the Ask section, or DM them to us on Twitter or Instagram. We’ll be recording podcast episodes where we respond to your messages, so make sure you subscribe!



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