How to Plan Your Career Pivot: a Guide for Millennials and Gen Z
If you’re here, I imagine you’ve been working for 1–8 years, probably after a traditional undergraduate path, and you’re feeling a little lost and considering a career pivot¹. I’m going to list a few statements about myself that I imagine will resonate with other people who may read this, but are certainly not requisites for continuing on:
- As a child and teenager, I was told to work hard in school so I could get into a good college. I worked hard, and I got into a good college.
- In college, I felt pressure (from myself, from peers, from parents, from faculty) to be successful by having good grades, doing impressive summer internships, taking advantage of cultural opportunities in my city, being/having fun, and managing my personal health. I did my best to manage that, with the last one usually being the first to go.
- Spring semester of my senior year, in the months before graduation, every person I spoke to asked, “What are you doing next?” This conversation was stressful. It felt like every student around me was going to do a fellowship or getting into law/medical school or using a mysterious pot of money to travel Asia and Europe. Everyone else seemed to have a great plan.
- I got my first job. It was a whole new world I didn’t feel that my life-to-date had prepared me for. I learned whole new muscles on everything from discovering the attempt at “work-life balance” to budget management (taxes, ew) to interpersonal office drama. For the first time in my life, I wasn’t on a conveyor belt towards what “success” was. I realized it was up to me to make choices about what the rest of my life would be like, and it was lowkey terrifying.
Who am I and why I am writing this
I am not an expert in anything but my own lived experience (a white-passing 28-year-old American cisgender woman who grew up on Army bases and overuses “lol” as a text crutch). Since I graduated undergrad in 2014, I have made several significant life choices. I have quit three full-time jobs. I have moved multiple times and have lived in New York City, Providence, New Orleans, and Pittsburgh. I left the comfort of corporate life to do a Venture for America Fellowship. I think my biggest decision occurred when I left a job after almost three years to go full-time freelance and simultaneously apply to grad school. This year, I started an MFA in Fiction, a long held dream. Over the past few years, about a dozen people in my age group (early to late 20s — millennials + Gen Z²) have asked me for advice about life paths and pivoting. It ultimately all came down to this question: “How do I know what to do next with life?”
This long blog post attempts to answer that question. It is not a guide on how to find a job or how to start freelancing or how to be successful (lol) (see, there it is). Rather, it’s a collection of reflections and links and concrete steps for young people (who probably don’t have a trust fund) who are trying to design their own life.
As of posting this, I am in a pretty great (for me) life stage. I see a lot of friends in my networks that don’t feel happy with where they’re at and where they’ve ended up. They’re in all different industries, and different life moments; some are in their late 30s, others in early 20s. What they have in common: a lack of alignment between what they’re doing day-to-day and with some undefinable sense of purpose/joy/values/desire. I write this because I want to help those friends and others; I am not an expert in career development or transitions — so consider this blog the way you might as advice from a friend’s older sister or at a networking event. That is to say, a well-intentioned stranger who wants to help you find your best life as you reflect over the course of several months to a few years. This blog post is an attempt to articulate what I’ve learned from supportive parents and mentors, from peers and friends, from myself on my own journey of self-reflection, and from the internet. I hope it is valuable to someone out there.
This post is oriented along the following journey that I think will be most useful for anyone asking the question, “What do I do next with my life?”
- Get to know yourself
- Get to know the art of the pivot itself and your industry
- Get comfortable with making a big decision, and how to know when to take the leap
Step 1: Get to know yourself.
No matter what stage you’re at, whether you’re a senior in college or a year into a crappy job and want to get out or plodding along for years in a “fine enough” role doing your best, you can’t make an informed decision about your life without being informed on the most important factor: you.
I’m not talking about your favorite color or what Hogwarts house you are. I’m talking about the deep stuff. What are your dreams? What do you want to accomplish before you die? What ways do you hold yourself back? What do you love about yourself?
During my biggest pivot, I took time to get to know myself BEFORE I quit my job, BEFORE I started hustling on freelance full-time, BEFORE I spent a lot of money. Here is what I did, much of which you can do for free or for low-cost:
→ A. Do a life audit.
Do a life audit [link]. This is a great activity made up by Ximena Vengoechea, another person on Medium. You essentially get a bunch of post-it notes, and do a guided walkthrough of where you’re at in life and where you want to go. I took a Saturday to do this. I discovered I did have dreams like “live in Italy” that could wait for later, and dreams I wanted to achieve sooner like, “have a dog.” (I now have a dog.) I realized how much time I was spending socializing and drinking (I lived in New Orleans), and how I could cut back and try to spend more time on hobbies I enjoyed and missed. There’s no obvious “WHAT NOW” answer after a life audit, but you’ve got to be real with yourself about where you’re at right now before you proceed. And it’s a nice entry point for a long journey of self-reflection and growth.
→ B. Read a thought piece called “How to Pick a Career (That Actually Fits You and Why)” and do the associated worksheets.
Read this insanely long, insightful thought-piece from Wait But Why: “How to Pick a Career (That Actually Fits You and Why)” [link]. A friend who was going through his own journey sent this to me a few years ago, and I’ve continued to recommend it to others. This blog post helps break down (with casual, earnest language and illustrative stick figure comics) all of the factors that go into being the people we are. It makes you ask really hard questions of yourself about what you value and what your influences are in your life. At the end of this process, you may realize that making a positive impact on the world through a job is more important to you than the prestige level (or vice versa) or that what’s most important to you is a big salary or that you want something that will make your parents proud. There’s no shame in wanting what you want with regards to a career; I think it’s just important to be honest with yourself. Tim Urban (the writer behind Wait But Why) writes with genuine kindness to the reality of being a millennial/Gen Z born into a world of climate change, anxiety-inducing constant news internet bulletins, and fiscal insecurity. There are worksheets as well that you can download for free. Take your time — a long weekend, a week of weeknights after work— to read through this.
→ C. Go to therapy.
Go to therapy. I believe everybody should go to therapy. Even if you’re not dealing with a “particular something” (like grieving the loss of a loved one), therapy is really useful for getting to know your own head. I personally like cognitive behavioral therapy. In that work, a therapist listens to you and helps you learn how to listen to yourself. You start to recognize patterns in your own behaviors and thoughts, and you can learn how to better manage your own anger, sadness, anxiety, hope, and more. Here is a great resource on what you can expect from therapy [link].
How to find a therapist
- You can use a database like PsychologyToday to sort through therapists that are accepting new patients with your insurance and what their specialities are [link].
- The suicide hotline is always free (800–273–8255), and also now has a chat function: [link].
- You may also try a virtual therapy service like BetterHelp and TalkSpace, which can help you find counseling that fits your budget and lifestyle.
- There are a lot of great sites out there for specific groups that you can find by Googling your needs including “How to Find and Fund Therapy as a BIPOC³”, the Asian Mental Health Directory, Mental Health Resources for Veterans and Military Families, Resources for LGTBQ Youth from The Trevor Project, etc.
Alternative/additional note: you might consider paying for a life coach. These are professionals whose job it is to help you work through professional (and some personal) life pivots, how to develop yourself as a leader, and figure out what’s important to you in your career. (I think you can do a lot of the work you would get from a life coach — at this stage in your life, anyway — by doing the first two seriously and taking the time to do them.) A life/professional coach is not the same as a job headhunter or an industry coach/mentor. It is also not the same as an executive coach, which is also a great investment if you’re in a leadership position and are trying to improve yourself and your management skills.
→ D. Attend a professional development program.
Attend a program whose purpose is to help you grow. I heard of a professional development workshop called “StartingBloc” [link] that a few other people I knew had done. I was able to get my full-time job to comp my ticket to be a StartingBloc Fellow (I still had to apply) because we had a budget for professional development. It was a great week of my life in New Orleans. I was essentially on vacation from my job, but I wasn’t just hanging out…I was surrounded by 50+ other people who were at a similar life moment to me (curious about what was next). We spent that week in targeted workshops and sessions all about reflecting, growing, and evolving.
There are many kinds of programs like this you could do, some for free and some for pay. Maybe for you it’s a yoga retreat or a trip into the woods with a guided notebook. Maybe it’s a more structured program like StartingBloc. You can also find programs that are specialized for an aspect of your identity; for example, post 9/11 military veterans who are considering life after service should consider initiatives like The Mission Continues and Team Rubicon. Regardless of what you choose, finding time like this to take a step back and reflect is really special. With programs like this, you get out of it what you give.
→ E. Establish your own goal management system.
Create systems for yourself about how to manage your goals. When you’re going through changes and evolving, you may identify that you want to achieve Goal A in a year from now. But in order to get there, there are several mini steps every week and day until that year mark⁴. For example: if your goal is to have a new job a year from now, then start identifying tasks you can do to ready yourself for that. Your tasks for a month may include starting to learn a new skill, attending two networking events, and having three informational interviews. (More on informational interviews and testing things out in the next section.) During this month of goal building and achieving, you may find that, for example, that after trying coding for a month, you don’t enjoy it after all and that’s TOTALLY OKAY and you can pivot (within the pivot!) and create a new goal to work towards.
I personally need a bit of structure and guidance, and I have found the Ink & Volt Planners [link; pictured above] to be the most useful to me (suggested by another millennial; I had met her through work and knew she was a freelancer, so I asked her for advice in managing side projects!). There are tons of great notebooks [link to a list] and apps [link to a list] and strategies for identifying and managing goals. Do some experimenting and find out what works for you. The key is to find something that forces you to reflect at junctures (like at a month, a quarter, a year) and to communicate with yourself.
Note: goal management systems are great for things besides career-pathing. You’ve probably known (or are) someone with a fitness plan. Maybe you’re working on a long-form art or technical project. But you can really do goal management with just about anything: I know someone who wanted to start dating for the first time but felt insecure about it, so she made herself a goal-based plan to get into it with goals like “send 5 messages per week on Hinge” or “have 1 coffee date per week” or “ask 1 friend for dating advice this month” etc. Imagine your dreams — and then make a plan to get there.
Step 2: Getting to know the art of the pivot itself and your industry
→ Get comfortable with the pivot itself by reading a book called SO GOOD THEY CAN’T IGNORE YOU
If you go to the self-help section of a bookstore, you’ll find a lot there about career finding and soul searching (a lot of them have the word “parachute” in them). I’ve read a lot of these, tbh. And, spoiler alert, I don’t think you need to read them if you’re doing the above exercises in Step 1. There is one book I consistently recommend (so much so that I’ve gifted it to at least two friends going through the pivot struggle) is So Good They Can’t Ignore You. It’s by a scientific and econ researcher named Cal Newport who essentially interviewed a lot of people who are successful within their fields because they’ve done opposite of the unhelpful “Follow Your Dreams!!!” mantra. It supports the stat that Malcolm Gladwell coined that it takes 10,000 hours to get really good at something (which has been echoed by Ira Glass of NPR’s This American Life saying he was really bad at making radio shows and just kept doing it until he wasn’t).
My one beef with this book is that it takes a long time for Newport to profile someone who’s not a cisgender man. What I do love about this book is how it refuted a lot of the language that’s been hyped up in American culture about how to do work that you love and vice versa, and rather explored the reality that getting to a point of success is about hard work and commitment. My biggest takeaway lesson is this: even if you don’t know what’s next for you, focus on continually getting better at whatever your craft/skills are and taking advantage of smaller experiences (a conference, a stretch project) so that way when the right opportunity does come along, you’re a great version of yourself to apply for it.
The book’s title comes from advice by comedian Steve Martin who shared how he wasn’t successful in the stand-up circuit because his material just wasn’t strong enough. So he made himself so good that no one could ignore him. Steve Martin is also lauded in another aspect of the book in that he had a goal that he wanted to get good at playing the banjo. Talk show hosts and other performers made fun of him. He said, “Well, if I play the banjo every day for 10 years, I’ll have played the banjo every day for ten years.” The implication being that he’d get pretty good at it. And, after ten years, guess what y’all: he is pretty good at it. (He has an album on Spotify of bluegrass bops; I especially like “Clawhammer Medley.”)
So, all in all, I personally found this book to be very useful. It utilizes individual story narratives interweaved with research to make helpful comments about modern professional life. You can get all of this knowledge for free by checking it out from a library. Or buy it cheap on the internet (or for not-cheap from an independent bookstore if you can afford it!) and you can highlight it and make notes in the margins.
→ Get to know opportunities in your field by asking people to talk to you
What follows is a step-by-step guide for anyone who feels unsure of how to network and/or seek out mentors.
A. Ask other people to talk to you for 20–30 minute “informational interviews”
It’s free, and all it requires is a little bit of your nerves/pride/awkwardness. You’d be surprised how many people want to be helpful to others and feel like they have learned valuable knowledge they can pass on. The point of this is NOT to ask for a job. The point is literally to interview them for information about their own lived experience so that way you can reflect on their takeaways and compare that to what you’re looking for in your life.
B. How to find people to talk to
- Pull up your LinkedIn⁵ if you have one (and if not, make one), and look through your network and suggested network. Search for people who went to the same school as you. Search for people who have the job you think you want. Then look through their networks. Message them (see the next step) or ask a mutual connection for an e-introduction.⁶
- Ask people that you actually do know and respect if they have anyone they think you should talk to. Frame your ask clearly, such as, “Hey, I’m interested in talking to someone who works in Startup Education/UX Design/Medicine, do you know of anyone who might be willing to talk to me for 20 minutes and just chat about their experience?”
C. How to reach out to them
Send them a cold⁷ message that reads like this:
“Hi CoolPerson! My name’s Amanda Tien*. We’ve never met but we’re both Columbia grads;** I found you through LinkedIn. I would love to hear more about your role as a Popcorn Flavor Inventor.*** Would you be open to talking with me on a quick phone call for 20 minutes so I can pick your brain about your journey and experiences? I’m generally free weekdays after 4pm****; if you’re open to chatting, please feel free to let me know a few dates/times that would be good for you. Thank you for considering!”
*Obviously, tell them your name instead. **We met briefly at a conference in 2019 / We both know ABC person, they’re so great / I found you on LinkedIn after you posted about XYZ / etc. *** About your law school experience / about your time living in London / about building up public speaking skills as an engineer/ etc. **** These people are BUSY; by giving them some indication of your availability, you’ll make it easier for their response to be, “Yes, here are two dates that work for me” rather than just “yes.” Too much time coordinating back and forth and you are likely to lose their interest/patience in finding time with you. You want to reduce the amount of time between the ask and the call.
Note: In pre-COVID times, if you found someone in the same city as you, you could ask them to grab a coffee or a glass of wine at happy hour after work, somewhere convenient to their office. The polite thing to do is to offer/insist to buy their latte for them; they are giving you two incredibly precious resources: their earned wisdom and their time. Not only is it a respectful thing to do, but it also will make them in a better mood and be more receptive to talking again with you — so if you’re having trouble legitimizing spending the money for yourself and someone else, consider it a small investment in a relationship.
D. How to have the conversation
Once they say yes, ask them for their email address so you can send them a calendar invite (even if it’s through your personal gmail, that’s still good because these people are busy, time is precious, and you don’t want them to forget!) and ask for the best number to call them at. Even before COVID-19 and the ubiquitous Zoom panopticon, I personally preferred phone calls because it eliminates the visual overload that comes with seeing someone (wasting time commenting on each other’s Zoom background, feeling self conscious about how you look, having to monitor your own facial expression rather than take notes) and instead hones all attention on the contents of the conversation being had.
You call them. A little small talk at the beginning is okay. If they ask me something vague like, “How are you?” I might respond with, “I’m good today! It snowed a ton here in Pittsburgh and my dog loves it.” Mini weather chat, yadda yadda yadda, THEN make sure to transition to the point. Here’s the magic phrase: “Well, I want to be respectful of your time, do you mind if I ask you a few questions about XYZ now?”
Be prepared with open-ended questions like, “How did you decide that doing X was the right move for you?” or “What surprised you the most about Y?” and “What should someone doing Z consider before going into it?” Take notes as you go. And if you’re slow to respond after they talk, it’s okay to say, “This is so helpful, sorry I’m not talking a lot, I’m taking notes!”
After the call, send a follow-up email within 36 hours thanking them for their time; you can also ask if they know of anyone else who may be a good fit for you to talk to. Add them on LinkedIn if you’re not connected already.
E. If y’all really vibed, ask them to mentor you
Occasionally, you’ll get lucky and someone will offer to be your mentor, but this is rare. They might say, “Keep me posted on how it’s going,” and you should feel free to send them short emails in the future with updates or ask for another phone call after a month or two. If you really vibe and talk with them a few times, you can ask, “Would you be open to mentoring me?”
In essence, a mentor is really just someone who is open to having regular conversations with you about how you’re doing, questions you have about the industry, and maybe even connecting you with other people or resources. There’s no rule book to mentorship, but here are the typical parameters:
- it’s nice to check in a few times a year with this person (think annual quarters i.e. Jan-March, April-June, etc…) with a short email
- you as the Asker should initiate the reconnects
- you’d let them know what you want to talk about (example: “I’d love to tell you about this project I’m working on and get your thoughts on skill development”), and offer to catch up over coffee/wine.
You can also find mentors through formal mentorship networks (try googling one in your area, like “Philadelphia women in healthcare mentorship”) where you apply and are matched with a mentor. If you work for a corporate organization, there may even be an in-house mentorship program, which is great. Colleges often have alumni mentorship programs (older alum mentors younger alum).
Mentorship, like everything else on this list, is a “you get what you give” situation.
Mentors will come in and out of your life like seasons; you may talk to them a lot over a year or two of change, and then as you get more settled, you may just send them annual short emails with updates on your journey. Eventually, those will likely peter off, too, and they’ll get updates about your life through LinkedIn and will write short comments like, “Congrats, that’s so great!” The next time you’re in their city, you can offer to catch up in-person over lunch or something — the relationship slowly evolves from active mentor to a sort of friendly professional aunt/uncle who’s proud of you.
→ If you can, “test” the pivot you want to do
Take a cue from science (or from the startup scene) and test out something before you commit to it. Depending on what you’re doing, it can cost an investment of time and money. This can look really different depending on what you’re interested in, so here are some concrete examples:
- After several years of not writing, I wanted to try again but wasn’t sure if I could even do it and felt frustrated trying to write after a long day of work. I found a local community-run writing workshop and took an 8-week novel writing course. I think it was about $500.⁸ Easily best $500 I ever spent. It gave me structure, community, and time. Rather than apply right off the bat to an MFA in Writing⁹, I was able to really figure out if I still enjoyed writing and if I could build the muscle of doing the work. You can probably find a lot of classes by googling the thing that you want plus the name of your city.
- Another example of this: take a course in the thing you’re curious about (like data analysis or coding for example) online through a site like Coursera or Udemy that may not even be graded. Both of those sites have collections of free classes and frequently heavy discounts; when you’re ready to get serious, you can use courses to get certificates in new skills which will boost your resume for job transitions. See if you enjoy it enough to do it in your spare time.
- I found a freelance design gig to do on the side of full-time work.¹⁰ I slowly built up my confidence and my skills, and did a few at a time so I could test out the feeling of having to manage a lot of different conversations and projects before jumping into the deep end.
- In college, I did a lot of paid internships that helped me explore different industries. It definitely wasn’t the same thing as working full-time, but I kept my eyes open about what the experience of that industry looked like. I learned, for example, that I probably didn’t want to work in the film industry in L.A. after all because I didn’t like the Hollywood culture and driving constantly.
- If you’re in college or grad school, utilize your school’s Career Center to find internships in various fields. Chances are the people working there are underutilized by other students and would love to help you find something. (Alumni are also usually entitled to utilize a Career Center as well!)
- If you’re not in college, consider small ways you can explore a real-world experience. You could consider asking someone to shadow them for “a day-in-the-life,” watch a documentary about the industry you’re interested in, or get a part-time job or short volunteer stint.
- If you have a business or startup idea, you can apply to an incubator or trial it at a hack-a-thon type event. You don’t quit your job or anything. It’s probably something you just do for a long weekend. But you’ll get to explore it with other energetic people and find out if it really resonates with others before you commit years of your life to it.
- If you have a project you’re interested in that doesn’t need to be shared with others, then just try it! Set some parameters for yourself and just do it. For example, want to try woodworking to build a coffee table? Give yourself a budget, take the time to research how to build a table and what tools you need, go to the store and ask for advice, then spend a weekend trying to build the table. Want to try designing a website? Rinse and repeat the above, just with a website builder like Squarespace and perhaps doing it for free for someone that really needs it like a family-owned local restaurant.
- You can do good for yourself and your community by volunteering with your skill set. For example, a friend of mine volunteers teaching engineering and other STEM projects to young women in her area. She can discover a few things: 1) if she likes teaching and working with young people, 2) if she likes the content of the work/is excited about it, and 3) can feel good about being generous with her time. You can volunteer a skill you’re good at with a service like Catchafire that matches nonprofits to people donating their time. With volunteering, you’re able to build a portfolio/CV in real time and also help real people. For example, if you want to try more photography, volunteer with a local animal shelter and offer to take photos of dogs and cats for their adoption website (animals with better photos are more likely to get adopted!). You can also do copywriting for animal shelters! This is all to say — open your mind to what you’re good at (or want to get good at), and help other people while you’re at it.
→ Getting to know your industry: more reading
This sounds boring AF but read your industry’s periodicals for a few weeks. You will absorb a lot very quickly. For example, if you’re in marketing, read AdWeek and FastCompany; if you’re in tech, read the MIT Tech Review or IEEE Spectrum; if you want to explore culinary, check out Saveur or Gastronomica. (Did I not mention your industry? Google that shit! “Best magazines/journals/newspapers to read for _______”) If you don’t have a reading budget, you can find a lot of an issue’s articles online, print copies at your local library, or in a rack at Barnes & Noble that you can sit there and read. And, if you still find it boring, then maybe you’re not that interested in that industry after all.
Industry periodicals get into the nitty gritty of what’s new, what’s bleh, who’s doing great, who’s innovating, what’s a problem, what’s exciting. You’ll read job titles of people being interviewed and featured in articles. These insights into the industry might show you a world you’ve never seen before. And, it’ll likely be less painful/awkward than a one hour networking session (which was tough even before Zoom; that being said, networking events are still useful especially when you’re actively on the hunt for a gig).
I’ll never forget the first industry periodical that opened my eyes. I was just shopping at an Anthropologie for boho skirts on sale or something and saw an issue of their short-lived, wonderful journal called Anthology (rest in peace!) [link]. I bought it regularly for the next four years until it closed in 2015. Anthology was a magazine made by creative professionals (a term I had never heard before) that featured work by other creative professionals. There were features on graphic designers, on people who ran their own Etsy stores, on American women who had made a living abroad, musicians, interior designers, teachers, makers, entrepreneurs, artists…people who had made pivot after pivot to pursue a life that made them happy. It inspired me to see so many diverse, creative people doing diverse and creative things with their lives, and made me want to be one of them. An industry periodical should make you feel that way, too.
Step 3: Getting comfortable with making a big decision, and how to know when to take the leap
→ How to not have regrets
You will never know for sure if this is the right choice. There are several times in my life that I thought I was making the right decision (even if it didn’t ultimately go the way I planned or wanted). And the thing is, I was. I was making the best possible decision at that time. I truly do not feel I have regrets on any significant life choice, and that is an awesome feeling.
On a hiking trip during my senior year of college, I ended up talking to a rando I was seated next to on a park shuttle. That rando was a high school guidance counselor named Reagan who was traveling alone from Texas.¹¹ I (kind of jokingly) asked if he had any insights for a college student about to graduate who wasn’t feeling very confident about the world (remember my intro?). He gave me some of the best advice I have ever received, and I am giving it to you:
“With big decisions, take the time to reflect about the options. Make your pro-con lists, talk to your people, journal your thoughts, whatever your process is. Identify what you truly believe is the best possible option. Then, make the decision and commit. Don’t second guess it or you’ll make yourself crazy. You will never know for sure how a decision will pan out. But no matter what — weeks, months, years later — you’ll be able to look back at yourself with kindness and grace and tell yourself, ‘I made the best possible decision with what I knew at that time.’ And you won’t have regrets.”
→ How to know if it’s the right decision
My mom, a teacher with a psychology and art background, has been an incredible thought partner to me and many others in making decisions, big and small. I’ll tell her about a situation I’m having, and without fail, she says,
“Okay, let’s imagine: you do Option A. Try that decision on. Imagine that you have made that decision; how do you feel?
I then answer her, or I answer myself if I’m doing it in my own imagination/journaling.
“How do you feel about that decision 10 minutes from now?”
Rinse.
“How do you feel about that decision a week from now?”
Repeat.
“3 months from now? 1 year? 5 years?”
You can replace these numbers with whatever intervals you found useful. These are my personal favorite because these force you to put a decision into perspective.
Some decisions, you’ll find, may not be that big of a deal in the long run, or some actually do have a potential impact far beyond what you can see in the present moment.¹² This exercise regularly forces me to articulate why I was considering doing something and what I really felt I would gain or miss out on. It helps you define what is urgent and important versus what just feels urgent. You can’t predict for sure what will happen, but you know yourself and you can interrogate your own reality.
→ How to get comfortable with making decisions
Some of the most useful life guidance I heard was from a TED Talk several years ago. (At that time, TED talks were being shared constantly on Facebook, a social media platform that was integral and omnipresent to our lives, rather than what it is now, something mostly only our older relatives use regularly.) This one has stuck with me. It encourages you to frame decisions as OPPORTUNITIES — an opportunity to define your life and decide what your values are and what you want to see for yourself. It takes the fear and anxiety away, and replaces it with hope and power. Ruth Chang says it better than me:
In closing…
I originally called this section a TLDR¹³, but this is long for a reason. And that’s because if you want your life to be a certain way, you have to be willing to work for it. You have to take the time to read the things and feel kind of bad about yourself and then make a plan and try to get better. You have to be okay with failing on the way there. You just keep trying. I say to my best friend all the time, “Yeah, today wasn’t great, but I’ll try again tomorrow.” You have to take the time (instead of wasting the time however you choose to waste time) to be serious about personal development. There’s no end state. There’s no magic path. True stability is not possible. Stability, as well as peace and happiness and fulfillment, is always a work-in-progress. YOU are a work-in-progress. And that is okay. We all are. All we can do is be intentional about how we can choose to spend our time to make that work-in-progress into something we can enjoy and thrive in as much as possible.
Even for me, right now as I write this today, I feel that I am in a “dream version” of my current life stage, especially given the pandemic. I am filled with immense gratitude and the desire to help others. But I am also insecure; I know I’m not an expert. Will I come across like a trite asshole? Will people find this useful? Will I be unhappy at the next mini life stage? I don’t have answers to those questions! All I know is I feel good right now, at this moment. I know that I may receive criticism for this piece, and I accept that, because, on the flip side, I do believe it will help people I know, and I hope that it will help people I don’t know. I think so much knowledge about careers and industries are kept behind gates (of privilege, of power), and I don’t think that’s fair. I hope that this guide pulls back the curtain for some people. I will choose to be unafraid of failure by sharing this in the hopes that it does help somebody out there, and that, when it’s time for “my next step,” I will remember this gathered wisdom that has previously helped me be strong.
Wishing you courage, health, happiness, safety, and hope -
Amanda, a millennial trying her best
Footnotes
[1] For some people reading this, this may just be the founding stage of your career, rather than a pivot. “Pivots” are an “intentional, methodical process for nimbly navigating career changes” (as defined by career expert Jenny Blake in this Monster.com interview). So, you don’t need to have worked for 20 years for a “pivot” to occur. Pivots are really, in my understanding, just the choice to switch it up rather than stay at the same company (or industry path) for decades the way that many of our parents likely could and did. And not that there’s anything wrong with that. Just for a lot of us, it’s not an option for a variety of reasons. But that’s a whole other article and this is a footnote just based on the title lol whoops.
[2] You certainly do not have to be a millennial or Gen Z to get something out of this piece; this is just my assumption on who needs this/who will resonate with this, and my language is tailored as such. If you’re not in this age group, I think you could still find this piece useful! If you’re older than this group, perhaps your situation looks more like reflecting on the major you loved in college that didn’t translate to the job you have; maybe the volunteer gig you do is more compelling than your paying job, and you could consider ways to convert that into your full-time work; or maybe you have enough money now that you could go back to graduate school to pursue a long-term dream (I know of a writing professor who, after teaching for 20 years, went to nursing school because it was a dream she’d had for a while); maybe the career you want isn’t in the city that you’ve prioritized living in. Life gets more complicated as we get older, for sure — obligations, especially with family and housing, evolve. You may already know how to do things like network (in Step 2), but perhaps therapy in Step 1 is a more novice idea for you (which is something that millennials and Gen Z are much more comfortable talking about openly). So, all to say, I hope this is useful for other people, too, and I can only speak to my experience in life so far.
[3] BIPOC stands for Black, Indigenous, and People of Color, and is a relatively new terminology to be more inclusive of native peoples and create solidarity amongst all people of color. You can read more about why it’s important here.
[4] Consider that you’re laying a brick road — you might lay three bricks on Wednesday and seven bricks on Friday and one brick two weeks later; as long as you hit your monthly totals, by the end of the year, you’ll have a road. What you can’t do is expect to lay a thousand bricks in one day and be disappointed in yourself when, inevitably, you don’t accomplish a huge goal. Consistent effort will bring you closer to your goal than one-off big surges.
[5] LinkedIn is a truly useful professional networking platform, and right now, a lot of the people you probably want to talk to are on it. LinkedIn is one of the easiest ways to close the gap between you and them.
[6] This works. Quick example starting with 2 facts: 1. I used to give campus tours at my college, and 2. my LinkedIn title was “Creative Professional” for a while. A guy that was a senior (also a tour guide) when I was a freshman was searching his networks for a good friend of his who was trying to pivot from being a lawyer to a graphic designer, saw I was one of his few contacts with that as a LinkedIn Title, and asked if I would be willing to talk to his friend for 20 minutes. I barely knew this guy other than that he was a nice person during tour training who I only overlapped with for ONE YEAR OF COLLEGE almost ten years ago (whoo I feel old lol), but I was totally game to talk to this other perfectly nice woman about becoming a graphic designer. Why? I don’t know, I just wanted to be helpful. More people than you would imagine say yes. You just have to ask. The worst thing that happens is they say, “No, I’m busy.” They don’t write you down in a black notebook with emblazoned on the front with, “Annoying people to take revenge on who dared ask me for help!!!”
[7] A cold message means one that is random from the ether/from left field/from the internet. I.e. it literally came in from the cold. Before the internet, this was called “cold calling.” Like you might cold call a company you wanted to work for and literally say, “Hey, you’ve never heard of me, but I want to work for you!” People often admire the ambition and the courage of receiving a cold message. Sometimes people never respond to cold messages. But sometimes they do! And that’s great. A warm intro, in comparison, is one where another person makes the introduction for you. For example, you were in the college drama club with Maria, and you see on LinkedIn that Maria used to work for Chrissy Teigen, and you ask Maria if she would be open to doing a warm intro between you and Chrissy Teigen. Maria will then make a judgment call: does she remember good things about you? Is Chrissy open to making connections? If it all lines up, Maria will say, yes, would be happy to connect you with Chrissy, and Maria will start a new three-way email introducing you to Chrissy Teigen. You then reply all and say, “Thanks so much Maria, I’ll move you to bcc to spare your inbox, and Chrissy, thank you so much for being open to talk, do you have any availability to chat for half an hour on Friday?” By the way, if you know Chrissy Teigen, please consider giving me a warm intro to Chrissy Teigen.
[8] I recognize that this is a privilege to have $500 to spend on exploring a skill. At the time, I worked for a nonprofit and did freelance on the side. I actively saved money each month for expenditures like this and reviewed my spending habits (amazing how much I could save by just ordering less takeout…). Here is a list to 13 free online classes about personal finance management.
[9]I will likely write a separate blog post about this because it’s really tough to find helpful information out there.
[10] Would a guide on building up a freelance career be useful? IDK lmk.
[11] If you’re out there, Reagan, thank you my man. Hope you’re good.
[12] For example, I remember being asked to do a volunteer leadership position for one of my communities. Everyone — my peers, the org leadership — assumed I would do it. No one else was stepping up for the position; I felt morally obligated to be a good leader and do the work. But I actively didn’t want to do it because it would’ve taken a lot of additional time that I didn’t have, the asks would uncomfortably overlap with the same tasks I did for my full-time work (but this time without pay), and it would’ve put me in a tricky social position of having to try to frequently rally my disaffected peers. I asked my dad for advice, and he did this exercise of my mom’s with me and asked me to consider that I said yes to this ask. For the 10 minutes from now, I felt begrudging acceptance. For a week from now, I could tell I would feel a little social boon that people thought I was a good person they could count on. For 3 months from now, I was already frustrated and overworked and regretting it, feeling that I had been trapped into yet another obligation I didn’t want to do (common refrain for many womxn in America/the world, I am sure). For a year from now, I predicted I would feel like it hadn’t paid off socially or professionally, and what’s more, I’d be burnt out and slacking on it; I hate doing a bad job on things, so I’d be disappointed in myself, too. In five years I predicted that everyone would honestly forget I had even done the thing to begin with, and no real long term impact on the community would’ve been made whether I did it or not. And so in a rarity for me, I said “no.” It’s been almost three years since that decision, and I don’t regret it at all.
[13] TLDR = Too Long, Didn’t Read — i.e. a self-acknowledging summary usually included at the end when someone knows what they wrote was hella long ;)
