From the title of this post, you’re probably expecting something written by a boomer after finally turning in their work hat.
But I am actually 28 years old and have been (mostly) surviving on my own since I was 19.
I was luckier than most. I knew how to leverage my experiences when I unceremoniously found myself dropping out of school after my mother decided she couldn’t/wouldn’t help me get my degree. That never-completed English degree came in handy when “upselling” myself. Actually, I sold myself along the lines of, “ Hey, I’m brilliant, and I’m cheap because I don’t have a degree, and I need to eat.“
When those first gigs fizzled out, I had to live, so I got a job that semi-paid the bills. I cashiered for a parking company first at various concert venues, and then at a full-time position at one of their permanent locations.
Those were hard years. The ones spent working overnight freezing in a phone booth or standing for 14 hours at a stadium, the mental breakdown of knowing there was no shortcut to get me out of this moment. I learned that sometimes, the lesson isn’t to overcome but to endure.
Fast Forward to Today
Up until 2 weeks ago, I worked 64-hour work weeks. Hired at my current position in April, I maintained my weekend/overnight side job to the chagrin of my supervisor. He would constantly ask if I was okay saying if this was a money concern, it could be addressed. I shook it off claiming it was easy work. I didn’t have to do much, I said; I was fine. In truth, I wasn’t. I stayed because I was afraid. According to psychologists, there’s such a thing as a scarcity mindset. Long story short: When you grew up without, you continue to be panicked and worried even when you have enough to sustain. I was afraid that this job that seemed so great would find me lacking, and that I would be tossed out. That they wouldn’t need me because I was a “bonus” position. Unlike my fellow coworkers, I really don’t have a tangible work product to turn to and say, “Hey, look at my beautiful code.” My job is built on the sometimes abstract concept of culture, and that isn’t as easy to measure.
My second job was my safety net. Dealing with capricious bosses, I never felt secure because I knew that with one argument, I could find myself unemployed or underemployed. So I worked an additional 24-32 hours not even considering my commute, which could take an hour on public transportation. Honestly, I probably took more than a few years off my life living like this.
After working 64- to 72-hour work weeks for 4 years, I am now at a company where I work 40. There are no side jobs. There’s no hustling. I have one job. Now what? I wake up, and I’m in awe, like, “I made it. I have one job, and all my bills are paid.” I have my weekends back for the first time in 4 years. Sleep isn’t taken an hour or two at a time because I’m worried I’ll miss my alarm.
Embracing the Balance
I know I’m breaking millennial law here, but I’m going to say it: If you have the means, please slow down. Yes, I know “Chill don’t pay the bills,” but as someone who’s on the other side of this 40-hour work life, I have to say it’s miraculous if you prepare for it financially and emotionally.
Eastern Standard has an unlimited PTO policy. Let this sit with you for a moment: I worked as a weekend operator for $11.50/hour not more than 2 weeks ago, and I now have unlimited PTO. The concept blows my no-longer-little-more-than-minimum-wage mind. Like I can go and still have a job when I get back? And I’m going to get paid when I’m gone?! The truth is I’ve barely touched it so far. Hello scarcity mindset, my old friend.
Then I had lunch with one of our company partners, who told me about the early years and earlier fears when the partners worried they would be seen as flippant company owners gallivanting off while their employees slogged away if they took one day off. And it struck me that these concerns are shared on some level by everyone in an organization. Maybe it’s scarcity mindset, fear of failure, or anxiety that’s holding you back from a balanced life. No matter the root cause, you need to actively work on achieving a happy medium.
Steps to a Happy Work-Life Medium
100% — Give your all while you’re there. Do excellent work so when you go, you can actually be gone.
Start Small — Work from home consistently once a week. Go to a conference and stay an extra day. You have to train yourself to not be anchored to your office.
Make It Visible — Set those dates on your calendar as early as you can. This is as much a reminder to you as it is to others. Prep out of office reminders a week before you go as a way to ease your clients into the frame of you being unavailable. It can be sneakily done in a post scriptum note on your email. If you’re the office point person, list your status on Slack as on vacation.
Shhh — You are probably a workaholic (I’m one too, so you’re in good company). You’ll probably be poking your nose in while you're gone so you don’t feel left behind. You are allowed to poke in, but you are not allowed to engage! No thumbs ups or gifs in Slack, no commenting on workflows, you are in the proverbial corner unless you are intentionally tagged in by the office. Your office can initiate a conversation, but it needs to be for the mundane (i.e., “what’s the password for this?”) or “the world is on fire, and you have the only water hose left” scenario.
Prep — Work ahead as early as you can and keep a record of things you have done/need to do. I use Google Keep and my Google calendar for notes on meetings, which my office has access to so they can see what’s going on if I’m not around. One step further: List out your projects, possible problems, and key people. My system literally looks like “Project 1 — client confused on xyz — be prepared, they are prone to caps lock emails — usually requires phone call and screenshots to explain how how/why something happened.” You can make an excel spreadsheet and share with your department/point person for ease of access.
Point Person — If you have some project or client that you know needs more attention than most, prepare your point person: send an email to clients a few days before you are out of town introducing them formally as the person who will be the “temporary you”. Said person should be in your department and know your caseload. It also helps to bring them back a small gift (I recommend chocolate and candy from your destination).
Know the Madness — Your office is always quiet in September, or the office holiday party in December is mandatory. If you’re newer, talk to people who have been there the longest, your operations manager, and your fellow department people so you can get the lay of the land and plan accordingly. They can tell you the best days to work from home or when the office needs all hands on deck.
Ride the Wave — You’ve prepped yourself, your clients, and your people. You’ve done all you can do. You have controlled the variables you can control, so go.
What the Office Can Do
Start looking at your data — specifically, time records. Which employees haven’t taken any time for any reason or a small amount of time has been used. Have they done work from home? Have they taken a vacation? Talk to these individuals and do a basic walkthrough of requesting time off. Talk to those who have used it the most and understand why they’re so comfortable using it as they do. Pass those findings onto those who are reticent to use it.
Make it a part of the culture and actually mean it. It’s easy to say we have unlimited PTO and WFH, but it doesn’t mean anything if people aren’t supported in using it. Everyone from the partners to the newest employee should be encouraged in using these benefits.
If they don’t use them, you make them. Eastern Standard has a “Take A Day” policy. Leadership and employees will nominate a person to take a day to themselves. People have gone to the spas and museums at the company’s expense. It’s a simple way of encouraging people who may not have found their happy medium yet.
Finally, limit conversation to people who are on vacation via Slack, email, or phone. Think before you type! The big thoughts should always be: Can I get this information anywhere else? Have I tried the point person? Did I go over their project sheet? If you still don’t have the answer, you are allowed to reach out.
Employees want to do great work, and employers need happy workers who want to be there. You’ll eventually realize the world won’t come to an end any sooner if you’re sipping mojitos on the beach or peeping in on your Slack at the Louvre. As in all things, you must be balanced. Trust your team, trust yourself, and always have a detailed script for when you’re gone.
P.S. After I wrote this blog, I was approved for a 10-day vacation in November. There’s hope for all of us.