Chapter 1
Are You Lost?

Your dream job doesn't exist. If there was a single piece of advice I wish I had known the day I started my first job out of college, it's this. Young adults are not prepared for “real life.” No amount of internships or college classes can equip you for the realities that are corporate America and the working world. It's a tough lesson to learn, but once you realize it, you're ready to take your career to the next level.

The Nine-to-Five Fallacy

It's likely you grew up with an idea of what your dream job would be. For me, I always thought I'd be a lawyer or a doctor or something very professional and highly regarded. This is because I was told in school that I was smart and capable, and the results spoke for themselves: I got straight As, I rarely struggled, and I didn't have a hard time getting into the college of my choice. Because of my academic experience, I figured it only made sense for me to pursue an elite career path. I had no idea what it actually took to enter these fields.

College humbled me. Straight As weren't easy anymore.

The thought of taking a college-level science class? Hell no.

The idea of struggling through a political history class with 48 hours' worth of reading a week? Not a chance.

I ended up choosing business—finance, specifically. Money has always been my thing. Not only were my classes interesting, but the information came easily to me. I loved the numbers, I loved working in Excel, and I loved sitting in the finance lab watching the trading board flash stock prices while I did my homework.

In the fall semester of my senior year, I landed my first post-grad job. I had done a few different internships over the course of my college career, so I thought I knew everything. I'd interned in various sectors of the finance industry, I interviewed for a handful of different jobs, and I was psyched to score—what I thought was—my dream job.

It was at a huge financial firm based in downtown Boston. I had to dress professionally every day. I was important. I was going to be living the dream.

TL;DR: It was not dreamy. I did not have a good time.

In this chapter, I share some of the most important lessons I learned from this job experience, along with the tumultuous career journey I experienced that transformed the way I approach work.

Lesson 1: No One Knows What They're Doing

This was the most surprising realization for me. At first, I figured it was unique to the company. Maybe the culture there was lackadaisical, and I just ended up in a fluke department. But this wasn't the case. Throughout my next two jobs, I noticed similar patterns. The “adults” who I always looked to for guidance and advice? They were just making things up as they went.

I always thought that everyone around me was smarter, more capable, and knew so much more than me. I spent a lot of time thinking that I was hired by mistake; maybe I am just good at interviewing and making other people think I'm smart, when really, I'm just an idiot.

But the truth is that no one has any idea what's going on, or what they're doing. It doesn't matter if it's your first year working or if you've been on the grind for more than 10 years: if you don't know the answer or the solution … just make it up.

My best advice? Stop pretending you know what you're doing. You and I both know that you're making things up as you go and hoping no one notices. Thinking that anyone else knows what's going on is an illusion, and it's causing you to doubt your own capabilities.

Lesson 2: Your Job Is Only One Part of Your Life

It is not your whole life! A nine-to-five job requires more time than simply the hours between 9 a.m. and 5 p.m. More often than not, there is at least one hour of the day for the commute, plus the time spent before and after both preparing for, and unwinding from, the workday.

Do the math: if you're awake from 7 a.m. to 10 p.m. on any given day, it's likely your schedule looks something along the lines of this:

• 7:00–8:30 a.m.: Wake up, coffee, get dressed, pack your bag, eat breakfast. You're doing all the necessary things to get ready for the day.
• 8:30–9:00 a.m.: Commute to work (assuming you have a short commute).
• 9:00 a.m.–5 p.m.: Work.
• 5:00–5:30 p.m.: Commute home.
• 5:30–7:00 p.m.: Exercise/some type of self-care activity.
• 7:00–8:00 p.m.: Shower, eat dinner.
• 8:00–10:00 p.m.: Relax.

Essentially, you only have about two hours a day for your own personal time. With the aftermath of the pandemic, luckily work from home has become a much more normalized practice, eliminating the commute and gifting some time back into the day for personal endeavors.

However, utilizing that personal time outside of a nine-to-five can be challenging for a few reasons. One being that many nine-to-five jobs are not actually nine-to-five; oftentimes they can look more like an eight-to-six or even a seven-to-seven, depending on your line of work.

Beyond that, working is exhausting. It's normal to feel mentally and physically wiped after a long day, whether you were in the office or not. This means that using that small amount of free time that you do have to nurture relationships, focus on a side hustle, or dedicate to personal hobbies is even harder.

I struggled finding purpose outside of my job for many years. A disproportionate amount of my life revolved around work: I lived in the city where my office was, my gym was around the corner, and many of my friends were coworkers. I found that in the few hours of personal time that I did have, I spent watching TV because I was so tired.

I fell into a trance: every day felt the same, and I wasn't working toward anything tangible. All of my life I had always been working toward the next big thing: in middle school, it was preparing for high school. In high school, it was preparing for college. In college, it was preparing to land a job.

Now I was in that job, and the next step was up to me. I was lost. I had no purpose, and I felt unstable in my life. It wasn't until I decentralized work and focused on building the life that I wanted that I started to feel more in control.

Work is only one pillar of your life. If you want to have a life outside of your job, you need to treat your job as what it is: a job, not your everything.

Lesson 3: Nothing about Work Is Glamorous

Maybe it was just me, but I always fantasized about “working in the city” and having a big glitzy office where I got my own cubicle and had all these important “work things” to do. Growing up, I always saw adults working, but I had no idea what they were actually doing. It sounds silly, but I was excited to finally find out!

I was hit with a big, fat reality check. There is absolutely nothing glamorous about working in a big office or in a cubicle. For the first few weeks of my job, I felt so cool commuting into Boston with my work bag and my business professional clothes. I had my own cubicle, they gave me a laptop and even business cards. I felt important!

Once I actually figured out what “work” was—an endless loop of circling back, following up, touch-bases, and Kanban boards—I realized that the reality of what I thought I'd be doing and what I was actually doing were quite different.

Whether you work in a high-rise office building with floor-to-ceiling windows in a major city or in an office park in the suburbs, work is work. Sure, the environment can make things exciting at first. But after a while, the environment becomes your normal; it loses its luster and becomes mundane.

I struggled with this a lot. For my whole life, I thought that working was going to be exciting and every day was a new opportunity for me. But after a while, the days blended together, and all of a sudden, years had gone by, and I was still feeling lost and unfulfilled.

The glamorization of work is entirely based on perception, both from what you want to be perceived as, as well as what you want others to think about you. Does it really matter if your job is perceived as being cool or important by other people if you hate what you're doing?

Lesson 4: If You Don't Own Your Career, No One Will

You are your own best advocate in the workplace. No one cares about your job and your career more than you do. Waiting for the next best opportunity to fall into your lap or for your manager to stick their neck out for you at performance review season is a surefire way to end up disappointed. Don't wait for others to advocate for you; advocate for yourself.

I always thought that when I felt ready for a promotion, I'd just get one. What I learned (the hard way) is that you don't get what you work for; you get what you ask for. There are a ton of strategies for this—from task-tracking to negotiation—and I will unpack all of them in detail in future chapters of this book. What you need to understand now is that you—and only you—are in the driver's seat of your career.

If you hate your job, you have control over leaving it. If you aren't getting paid what you deserve, you have control over finding another...