How To Get Out Of Retail

how working in retail management defines, breaks and humanizes you

You played Life. You understand that by the time you leave school you need to have a job. The decision to do something, anything is already made for you.

That's where my Apple journey began - a couple of months before crossing the graduation stage at UVA, in need of an income, and hypothetically excited for a fresh start.

Any job sounded cool because it was the logical collective next step. The, not my. You don't spend much time thinking about how to create the life that you want when you don't understand that it is yours to create.

Everyone around me seemed to have their shit together, so it didn't seem smart to outwardly express that I had no fucking clue and could really use some help here.

You get a job because it's expected and inevitable, and outside of the highly prestigious titles of doctor, lawyer or superman, they're all kind of the same thing, right?

I applied for a leadership development program that Apple Retail happened to be beta testing in spring 2010. Every person I met through the interview process was bright and shiny - they spoke with confidence, excitement and purpose.

When Apple Retail held out a warm hand, I ran towards it.

Most of the time I look back fondly, remembering it as one of the best parts of my twenties. Other times I remember it as the worst. What I didn't see while I was in it was how much this seemingly unconventional choice changed me for the better.

Apple taught me to:

hustle
work with purpose
see the world as a friendly place
start with why
take life in my own hands
look backwards to move forwards

Update: since writing this article I've discovered JobStep, which helps retail and hospitality workers level up by helping you share your transferable skills in your resume, apply for jobs, and land 5 interviews in 6 weeks. A good friend enrolled in their pilot program last summer and now has a Director level job in tech. If you're looking, I highly recommend checking JobStep out! If you'd rather learn more first, read my interview with JobStep CEO Eleanor Meegoda.

hustle

Our group of ~150 spent the first two weeks of work in leadership development trainings. Myers Briggs, S.M.A.R.T. goals, mind tools, root cause analysis, learning blueprints, action plans, Net Promoter for our People, conflict management. They supplied framework after framework to help us make hard decisions on the road ahead the right way before any of us could see the road. What's the big thing that ties it all together?

The two year program was structured into ~10 milestones, with one for each of the individual contributor and leadership roles. Understand the role, practice it, identify and solve a problem within it, present your findings and #ontothenextone. We lived between two worlds, not quite peers with the team around us, not quite managers, largely unaware of the perceptions cast upon us as the inaugural class.

I immediately kind of hated myself for working in retail, for wasting the money my parents invested in me and my education to take on a job that, when shared with others, probably conjured images of "would you like fries with that" or a dead eyed person folding discount denim at a strip mall. But it was Apple, bright and shiny and recently dominating with the release of the iPhone. It was beyond retail. It was an experience.

I practiced a pitch that made me feel a little better and the audience that asked "what do you do for work" a little less uncomfortable. Apple, as a brand name, was sexy. Corporate. Important. Age 21, these are appealing attributes. So I'd say that I work for Apple, drop the retail. I'd tell people how many millions of dollars each store did in volume, how big my team was, how often I had an audience with important people within the company. What I didn't get until years later is that the discomfort of every person I talked to was simply a reflection of my own.

It never felt good to describe to the outside world, but when I was in it, I loved it. I fell in love with the people on each team I worked with and the things we did each day to keep the store running. At peak moments - holiday shopping, iPhone launch weekends and the weeks that followed, most weekends 2010-2015, Apple was my concrete playground.

There was something calming about the cyclical nature of retail seasonality and Apple product and software releases, and the routine of each workday. The ability of a smile and a patient, listening ear to turn around a terrible customer experience. I had a feeling that if I wasn't there, the world may in fact fall apart, which created a sense of peace and power. Everyday, people came in with problems I didn't know how to solve and, 9 times out of 10, I experienced the instant gratification of I don't know, let's find out to solve those problems. I walked out everyday tired but happy, tank empty from running around.

Each store is its own unique node in the Apple network, but all share similar values and characteristics. Every store I've worked in looks like a 2010s United Colors of Bennetton ad and has a vibe. There are people from all walks of life: retail devotees, teachers working part time, college students trying to pay their rent, corporate people impacted by the recession and others, artists and dancers and musicians in need of solid health benefits, nomads just stopping by, entrepreneurs in search of a safety net. Everyone operates at some shy or outspoken level of Apple fan-person-dom, always waiting for the next launch.

purpose

On the sales floor, you put your blue armor on to engage in the endless battle between business, customer and team members. You build quick bonds with your leadership team, partially for survival but also through seeing everything everyone through. Work is one big open office and customers don't make appointments to see you, they just show up. This is an inherently great and supremely challenging thing. There's no lead qualification process in b2c; when the store opens each morning, so do the floodgates.

Friendships are forged over ludicrous customer/employee scenarios, the days that wear you down to the bone but crush all of your sales goals, and the glimmers of fulfillment you feel when everything is working in symphony together. The glowing customer buying their 1st or 10th Mac, the devastated and exhausted mom who dropped her phone in the sink and miraculously leaves with all of her photos intact and a fuller heart but untouched wallet. Thanks, iCloud.

Your peers and bosses and high potential people keep you going, their fire stoking yours. You show up everyday for these people, your team. You are bonded together by the intensity of each day and inflection point - Genius Bar appointments that start and/or end in screams, free and wild coworkers dancing their way across the sales floor, 15 minute breaks in the managers office actually LOLing at nothing in particular.

As with many jobs though, it becomes less fun over time. Routine begins to feel like a rut. People come and go. The purpose instilled by the original bright eyed people is questioned or even lost with each changing of the guard. Your energy sustains you, but you have the creeping feeling that at any moment, it might run out. Why am I here?

You sit in the manager's office for a little longer each week, desperate for time to be still instead of reacting to stuff or doing the same fucking thing over and over again. The smiles and connections become increasingly superficial. Your brain starts to shuts down or you shut it down. You don't remember making a conscious decision to do this. The basics happen automatically, theoretically creating space for higher level functioning. The elevator was moving up but you're stuck between floors.

When you get good enough at your work that you tune out, everything becomes easier at first. You take lengthy mental vacations to nowhere. This makes it easier to handle the barrage of iPhone owners that are also investors in the company that really cannot believe that you won't replace the phone that was run over by a car for free.

You slip into mindless routine. Easier is easier. It lets you tune out for 90% of the workday and just get on with it. And you could do more but no one is standing over you yelling at you, so you don't. You're an adult, you can eat cereal for dinner. Honey badger don't give a fuck.

This isn't enough for many millennials though. I'm not sure, but as a millennial, I think this is part of why you see the drive to change jobs so frequently and keep pushing for more. We all saw 8 Mile, we get on a theoretical level at least that life is a one chance, one shot situation. Some people understand that to survive, they have to choose to stay and tolerate it or get the hell out of dodge. They also understand that by not engaging fully with the bad stuff, they can't engage fully in the good stuff. These are the people that ask themselves honestly when's the last time you were truly happy? what's something you're grateful for today? and when hearing the same bad response too many days in a row, do something about it. More purpose, please.

There are people that stay with Apple Retail for double digit years. Some may seem stuck, but many find their purpose and value in the work. I saw it and was jealous of them and their purity. These people were aware of all of the things that make people stop drinking the Apple kool-aid, and yet they carry on. The setting, the cyclical nature of the work doesn't matter. Apple is an opportunity to mentor and develop and grow. They were like trees offering shade to all of the lost souls in the stores, acknowledged and celebrated for it but never doing any of what they did for the recognition.

I vividly remember working with a team on a project presented to Regional Managers, the people that oversee the District Leaders who oversee the Store Leaders who oversaw us/me - people who had made their careers in retail environments with 20+ years of experience. We shared what we thought to be true about ways to improve the stores that we'd been working in for maybe 8 months at the time. It was, as many of these sorts of things are, neither great nor terrible, although I'm sure we all patted ourselves on the back at the time. You don't remember what people say, but you remember how they make you feel, right? We probably made them bored. One of them made us, or at least me, further despondent about the decision to work in retail in the first place. "Corporate? No. You'll never work in corporate." That is, I think, the aspiration of all of the people that work at the stores who really want to get the hell out of retail, so 75%+ of the people in the stores. The lies I told the world and myself about the career trajectory came crashing down in a single sentence. You are in a dead end job and nothing will change that.

When you remember to look up, you remember this and drink enough wine on a Monday-this-is-my-weekend-night to Google stuff like "how to get the hell out of retail." The results are dismal, sending you down a deeper spiral.

If you talk to people who are not in it with you, they will offer you advice. Advice is so terrible. Advice is, for the person who is struggling to admit to themselves that they have a problem, the last thing that is welcome. People think that they understand but they don't. They've had a head cold before, you have a fractured femur. They don't understand the problem, and you probably think that they don't want to. To engage with your mess of a life is to have to know the suffering of others and to confront their own.

The blue shirts were a badge and a burden. I wanted the agency of my own office, schedule and wardrobe. Things I'd never really valued up until that point. As with everything, to know how much you need it, take it away.

perspective

This is all starting to sound very whiny. The whine that you hear as you read is an honest reflection on how I felt in moments and many weeks in the years that followed. You may go forward, but only so far. This is the box. The box ends here. Do I make myself clear?

Those who were much wiser than me saw it differently. Apple Retail is, in fact, a huge box to grow in, up down and sideways. These wiser, endlessly curious people learned something new everyday about a product or a person or both. Selfless coaches and players that understood their job and wanted to be really good at it while being human first. They made the box bigger for the people around them, both actually and in feeling. Titles and prestige and power mattered naught to them because they got it. They got themselves.

How many 20-somethings really get themselves, though? I was on leadership teams surrounded by a melange of better/wiser/older and youth - I won't categorize that positively or negatively, but I think you know what I mean.

Somehow, Apple understood. They understood not only the need for development to give actionable advice to help us manage our businesses, but to quench the thirst for purpose. What you're doing matters not because it makes us, big corporate entity, richer, but because you have the capacity to help those around you do more, better, faster. At Apple, the heart of our company, our soul, is our people.

When you see a word with huge meaning: body, mind, soul - how fully do you engage with it? The credo card and all that's inside of it and the Apple Retail ecosystem was created very mindfully. The team behind Apple Retail developed a best in class learning management system to help people learn the core things needed to do their jobs well: sell people the stuff that they need even if they don't know that they want it yet, don't piss people off, take your breaks on time, understand what it is that we're doing here. All of these resources were easily consumed mindlessly though. Read this, then do that. As with most work, it was easier to digest business first with a little song and dance than with real thought or discussion. What's the big thing that ties it all together?

There wasn't a single day that I opened the credo card we held in the lanyards draped around our necks and pondered soul, as a concept or within myself. I probably could have saved a lot of time on my journey to self discovery if only I had taken a theology or philosophy class in college. If only.

In my first two post retail jobs, I wondered if the real world was obscured from retail employees intentionally. Make sure people know how good they have it and how scary the world is out there. I imagined greener grass sometimes, but I never saw it. What is grass? I would wonder. I understood the mechanics of a retail store inside out, but didn't know what people did that work at offices all day. I didn't know, and didn't bother pausing to contemplate. Ignorance is bliss; I was worried that if I tried to understand, broaden my awareness, I would just see all of the things that I didn't have, couldn't have, wasn't worthy of. Do you ever do that? Everytime I went to update my resume I told myself why I shouldn't. It occurred to me that putting myself out there and then not getting any interest or receiving straight up rejections would push me further into darkness. Once I start to look for greener grass, I will be even less happy where I am. So I stood still for awhile.

It's easy when you're low to assume that the world isn't there for you, and when it's high, to think that it is. What's hard from both vantage points is to ponder and entertain the possibility of the opposite.

You love and hate the cage that you keep yourself in. It is known, it is yours, and it is all there is.

That's kind of the point. You make a choice to be sort of miserable, to think that the world doesn't have your back. And not just in the moment that you are miserable, but in the hundreds of decisions that lead you to live a life of sort of misery. A new layer is added everyday that makes it a little harder to turn back or change course. The problem doesn't lie at rock bottom, it's in all of the things that you mindlessly do that bring you lower. And you can't get out of that place without facing the things that brought you there. This requires not only the courage to see and vanquish your fears, but a willingness to be present. To use your head and your heart symbiotically to find and face and hug and love yourself. That's the thing. Are you willing to do whatever it takes to look at yourself in the mirror and love you, accept you? Not in a "I'm going out tonight and I look fucking good" kind of way, or a "I did a thing that I am proud of and can tell people about" kind of way, but in a "I see my flawed and fucked up self and I love me" kind of way. It's easy to be ok when everything is going well. It feels impossible to be ok when nothing is.

Every failure could be a badge of honor, applauding the bravery required to try and mess up and keep trying with everything you have. Instead, you beat yourself over the head with your failures, often using them as excuses that get in the way of greatness. Getting in your own way is easy, getting out of your own way is hard.

There is a nagging feeling that you have wasted all of the potential within you and the time, money and energy of every person who helped you get to this point to only get to this point. You didn't come so far to only come so far. You don't see yourself at the beginning, you are just immediately pulled into needing to be better and further along at the game of life.

No one tells you that you can get out of retail so you think that you can't. No one tells you that you can dream big and beyond so you don't. No one reminds you that you are just beginning, and you are right where you need to be.

living

I, like many, didn't look for an out until I felt like I had to. The real world was a scary place and I was successful. Comfortable. When I walked out of the giant glass doors to take maternity leave, I knew that I probably wasn't going to come back.

You have to work up the courage to let yourself start your search. Extrinsic motivations guide us, especially in young adulthood. But at some point this breaks, or you break it. What do I want? What do i need? No one else is going to save your life. This recognition requires that you wake up, turning yourself off auto-pilot to go off-roading. You don't like this road that much, anyways.

Before you change direction, you look in your rear view mirror and when you pause to look back, you see how far you've come. In addition to the routine work you busy yourself doing, you did other, awesome things - not for your resume, but because you wanted to contribute at a higher level, work with new/more/different people, challenge yourself. You tarnished your own accomplishments by adding a retail label and stuck them on a worthless shelf without seeing that the things you bragged about out of shame for years are in fact brag worthy.

You zoom out and in. Seeing everything and seeing just what you have in this exact moment. The whole can overwhelm you to the point of inaction, even with the understanding that you have. How do you begin again? How do you start?

To make a step, you look at the things inches and feet in front of you over and over again and you begin to process what it is that you're experiencing. What does your life look like? How are you spending time? Who are you spending time with? Where are you going? Can you see the path you're on, and are you really here for the ride? How do these things align with the values you claim to care so much about?

With this understanding, you see your strength and accept that movement in any direction is positive because the alternative, stasis, is too mindnumbing.

why

In beginning to look back, you start to see the value of the practical education you've received through retail.

No person comes in to get a thing, each comes in in search of a thing to fulfill a purpose. Their journey started long before they walked through your big glass doors. You start with the why at the heart of their purchase or support request, not the thing, never the thing. You're given a set of commandants to follow, the apple steps of service. You learn how to talk to customers and then your friends and family with the framework of the three As: acknowledge, align, assure. Ask for permission to move forward, then position a solution that meets the needs they've identified, repeating those needs back to them. Listen for the concerns that they bring up and repeat APP before ending with a white and silver apple bag, and a fond farewell. Until next time.

As you sell hundreds of thousands of dollars of shiny, beautiful things, you think that you're practicing the art of the sale. The framework you follow to help each person becomes mindless enough that you can disconnect from it, go somewhere else while you watch yourself going through the motions. But really, you're being taught the most important thing of all - how to care, how to give a fuck, how to genuinely connect. And that can take you almost anywhere.

Working for the best retailer in the world, problem solving with people day in and day out teaches you things that a classroom cannot. You learn:

Equanimity: You meet drama with empathy and humor, and are able to see both sides of every argument. You know how to be patient, charming, friendly, and fun.
Composure: You can keep a stiff upper lip in the worst of times because you have already experienced the opposite in the worst of times. You have seen the worst of times. You are resilient.
Candor: You understand radical candor, not because you've read the book, but because you've had the hardest heart to hearts with team members and strangers.
Restraint: You also understand the importance of privacy and can learn to read the room to know when to stfu, because you know the fallout that waits on the other side.
Presentation skills: You can present to a roomful of people on a dime because you've done it enough times to not suck.
Change agility: You are presented with new challenges daily and are always learning, and crafty in a non-sketchy way.
Humility: You change course quickly and get a lot of stuff wrong, and have to be ok saying "I don't know, let's find out." If you can accept it, it can become an opportunity to build trust.
Teamwork: You work with an open hearted army of people who wake up every day and put the needs of others before their own. This teaches you how to be a servant leader and more importantly makes you want to be a servant leader.

This is the magic of every person who has held down a job at a bar or restaurant or retail store. The thing that seems like its crushing your soul - servicing other people - is the very thing that saves it. You've gotten as many things wrong as you have right but the score doesn't really matter, as long as it helps you make better decisions moving forward. You have hard won human experience that is directly transferable to so many places in the world - you just don't know it yet. You have learned the hardest thing of all; how to be human, how to connect. Now go be one.

This is progress. You can never really turn back once you begin to look within yourself. There is only forward, although the path may seem splintered at times. All of the pieces of your life will connect if you put the puzzle together. You can do it mechanically, mindlessly, and hope that it all sorts itself out on its own, or assemble with the unhindered enthusiasm of a person working towards their dream job, life, this moment, this thing right in front of your fucking face.

It's just like the game and nothing like it. It's whatever you make it if you begin to make choices. You take responsibility for where you're at and where you need to go and the gap between, as scary as it is. You were passive, you are active.

This challenges your values, which challenges the very fiber of your existence. What does it mean to be authentically you?

When you've lived in a floating state for so long, the values that you eventually identify come into focus so quickly and clearly that they come down hard. You reckon with their assuredness, pillars you use to consciously and unconsciously prop yourself up as you move forward.

You'll feel clumsy about everything you're doing until it is yours, a choice you have actively made to do or not do things vs always taking the path of least resistance and going with the flow. The bright and shiny people have made choices to be where they are, and have made peace with the things that impact them that are outside of their control.

Do not minimize your own story, your own truth. Do not build additions to the fractured foundations of other people who are not you, that you do not understand. Do your research, find your soul. If you like a place, you can build your own house in the same neighborhood from the ground up once you do understand. You know you don't need to have it all figured out on a surface level but maybe you don't really believe that, forever pulled to make decisions and take action faster to keep pace with your peers and enemies.

onward

I worked for Apple retail for 5 years, cutting my teeth as a leader working with 100 person teams on hard AF concrete sales floors.

Working at Apple taught me the importance of listening, what it means to be a servant leader & how to have fun at work while being obsessive about the employee and customer experience.

It also taught me humility - putting on the same blue shirt as everyone else on my team, working crazy hours, and being endlessly open to fearless feedback from team members and stockholders.

During the best times, we got to have fun because we were hitting/crushing our numbers (and we were hitting/crushing our numbers because we were having fun). During the worst, the team and the hustle and the occasional reminder to look and listen kept me going.

Sometimes I miss it. Maybe I would have turned a corner and, getting so good at the basic job functions, finally seen the meta-game.

"You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something – your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road will give you the confidence to follow your ❤️even when it leads you off the well worn path; and that will make all the difference." - Steve Jobs

You learn as much as you can, you teach as much as you can, and then you move on. A good marker of your readiness is whether there are other people ready and able to step in and fill your shoes.

This exercise will develop others, prevent you from feeling like you're abandoning your team, and help you build confidence in the process. You know stuff, you are worthy, you got this.

It took me 5 years to learn how to be human, and another 5 to be conscious of my humanity. When I was there, I thought I'd squeezed out every last drop of wisdom and opportunity but in looking back I see how much further I had to grow. Have.

Advice is the worst but maybe, if you're still reading, you will take it from me. Write down your skills and interests. Consider what elements of your job energize vs deflate you. Talk to friends, relatives, friends of relatives to learn more about what they do. Search for job description templates online and see how your skills and interests and passions align and where the gaps are. How can you fill the gaps at your current job and/or in your free time? If you're a 75%+ match with a job description that interests you, start your search.

Your next step could be finding a new path within your four walls through other opportunities or educational assistance, or a step outside of them - sales, tech support, teaching, customer service, HR, operations, leadership, project management, product management, IT. The next thing isn't just the next step, it's your next step. You make a decision to push fear and insecurity aside and take a chance. You update your resume and draft a cover letter and from there it seems like everything gets easier. The first step is the hardest.

Your resume will require a lot of work. Don't let it overwhelm you. You have to connect the dots for the sourcers, recruiters and hiring managers that will review your resume. You have to do the work to showcase your transferable skills. Never assume the person screening your profile understands what you do working in retail or how it translates back to making a contribution at their company.

Doing NPS calls makes you a great problem solver. Running a queue at the genius bar makes you a great time manager, multi-tasker, customer service superhero. Selling a $3,000 computer to someone who came in considering an iPad makes you amazing at uncovering needs through consultative sales. Never calling out showcases your insane work ethic. Positive customer feedback shows how you build relationships quickly. Leading store initiatives demonstrates your project and maybe change management abilities. Hitting goals as a store team for multiple consecutive quarters shows consistency, and an ability to replicate success wherever you go next.

Many job boards offer a terrible candidate experience. Explore some of the ones that don't:

The Muse
Angel.co
Uncubed
Underdog.io
LinkedIn

Many companies have a bad candidate experience for the non-obvious applicants, too. Big companies have their job descriptions down pat, and often have the recruiting technology that screens for transferable skills over potential. Smaller companies and startups offer human connection. When you're getting started, a small and medium businesses give you the opportunity that big ones often won't: they see you and your potential. You can become a big fish there. Even if you don't, you can learn a lot more through osmosis; working side by side with the person who founded the company, the people who build the product, the sales team.

Know yourself enough to understand how well you perform with and without structure. A benefit of the retail job you have is the amount of training and development big companies offer to help you be good in your job. Many startups don't offer this, and if you aren't used to being a beginner, thinking outside the box and structuring your own time, a bigger company might be a better learning environment for you.

Read up on companies that have open positions and that match your vibe. Your team members and company culture will quickly matter more than your job title so do your homework before you start applying. Remember that no job you apply for expects you to be perfect, and many are willing to teach you. You bring value, you are enough. Apple is much more than a job, it's a vibe. Don't take the first non-retail thing that comes your way. Understand the impact on your life beyond giving you better hours and don't settle. You have spent time with the most magical human beings on earth, don't underestimate the importance of the team on how much you love your next job.

Yes, you can get the hell out of retail if you really want to and you're really ready, but replace retail with wherever you are if you've hit a company imposed ceiling on growth. I guess the question is: is your next job an escape or a portal? Are you running away from, or towards something else? No one wants to hire someone because they want to do something else. That's boring and aimless and easy to add to the declined pile. If you aren't happy where you are, how much of your unhappiness is because of factors outside of your control? How much of your unhappiness is because factors that you can control? It's clear that you know what you don't want to do. What do you want to do? No one else can answer this for you.

Move on and move forward with the belief that the world is here with you, not against you, and that you are ready to start over. If you weren't, you probably would have stopped reading a long time ago. Begin again.

Questions? Want to talk? Shoot me an email: haleymbryant+retail@gmail.com.