How to Crush It, Even If You’re Starting from the Bottom

Here’s some advice that doesn’t ignore reality.

Some people think they get a whole weekend for their birthday. Take one of my students. She missed a paper deadline before skipping class Friday and Monday. Came back on Wednesday to ask me for an extension. Oh, and she wondered if I could forgive those absences.

“You don’t have to tell me exactly what’s wrong,” I said. “But give me something to work with here.”

Maybe her sister had a car accident. Or her dad was undergoing emergency brain surgery. Maybe her house burned down.

These things happen all the time.

She took a deep breath and said, “It was my birthday weekend.” Then she started talking about self care.

“If you don’t take care of yourself, then you can’t take care of anyone else.” Oh, how enlightening. The tone in her voice, combined with her facial expression, told me that she’d just learned this phrase.

This aphorism doesn’t exactly define what it means to take care of yourself. Clue — it’s probably not skipping class for birthday cake.

Still, I gave her a deadline extension. Not because I believed what she was saying. Back then, I was working as a grad student at the kind of institution that serves students from the upper-middle class.

One of our dorms offered room service.

Their parents could make your life hell. None of us lowly TAs had time to go round and round with a 19-year-old about her life choices. The poorest of us were tutoring online 20 hours a week on top of teaching two classes and taking three. It was easier to let the students win.

Comfortable people can afford to fail.

Self-improvement sound bites give us lots of room to contort good advice into bad decisions. They also ignore undeniable truths about those of us living in the margins. People with money can afford to take risks and make mistakes. They can afford to fail more often.

Failure — so often celebrated as the prerequisite for success — hurts a lot more when you’re living below the poverty line.

Failure costs money, and time.

The advice coming from middle-class entrepreneurs doesn’t work for the rest of us. In fact, it makes dangerous assumptions. That’s why I’m trying to come up with some better, more realistic tips.

You’ll have to work way harder.

Back in my 20s, someone I knew described working at a firm run by her dad’s friend. She could take 2-hour breaks most days, in order to network over lunch with potential clients for her web design startup.

My friend was given easy jobs, and minimal expectations. She talked about hustling a lot, but she didn’t have to hustle as hard as we did. She “seized the day,” but her days came with benefits.

Her day job totaled about 30 hours a week, but it paid her downtown apartment. She drove a car financed by her parents.

She was still on their insurance.

It’s easy for a success coach to talk about drive and motivation. They glamorize the 14-hour day. In truth, a lot of us have no choice but to endure 40 hours a week at jobs we don’t care for.

At least for a while.

You’re not lazy. You’re human.

When you clock out after a shift waiting tables, or brewing lattes, you’re tired. And you should be. Wanting to have some box wine, watch some Netflix, and go to sleep is the natural response to working 8 hours — especially at a demanding job, with a boss who doesn’t care about you.

You don’t have a motivation problem. You’re normal.

But we all have to charge through some nights and weekends to pursue bigger, more ambitious goals. My third year in the doctoral program, it wasn’t unusual to stay awake and work for 30–40 hours straight. It was a weekly ritual. Then I’d crash for a 12-hour sleep marathon. It was super unhealthy, but that’s how I got the work done.

It’s not fair, but that’s okay. Sometimes the only way to create equality is to win by their rules, and then change the game for the people coming up behind us. That’s exactly why I try to make life a little easier for my current students. I know they’re all working jobs and raising kids.

You’ll have to work way smarter.

My grad program would never lay down $2K for the coding software I needed for my projects. Sure, I could’ve taken out a loan and bought it. That might qualify as an investment in myself.

But it was also a huge risk. Every major purchase on my credit card was something I’d have to pay off later. Visa had already bought me a computer, and I’d foregone a summer job the previous year to try and promote my first book. What a disaster. The only thing I learned from my book tour was not to do book tours anymore.

Like I said, failure hurts more when you’re on the poverty line. So, no fancy qualitative data coding software for me.

I had to get creative with Excel.

My university also never paid much for travel to conferences and archives. So I stitched together freelancing and tutoring jobs to cover the costs. My friends and I shared beds at lavish hotels — sometimes four to a room. We ate our dinners at the keynote receptions.

All this didn’t feel like hustling.

You’ll have to work way faster.

Sometimes, you can’t escape busy work. You have to hack it. A common piece of advice from middle-class entrepreneurs is to delegate and avoid. Well, guess who they’re delegating to? People like us.

So they “seize the day,” by basically robbing us of ours. When we complain, they tell us to delegate more.

So I’ve stopped listening to anyone who spouts this advice. You can’t just kick your busywork at someone else, or ignore it.

But you can automate it. I’m terrible at software design, but I at least know how to find Google add-ons that make my life easier. I’ve learned how to create my own templates to make paperwork faster.

Scanning chapters and articles for my classes can take forever. So I just slice the pages out with a box cutter and feed them through.

Much less pain. And now I have a PDF for myself. Our department secretary loves me, because I’m the only teacher who doesn’t try to load her down with photocopy requests.

I’ve configured my inbox to make email less of a pain. And I’ve turned time-consuming meetings into online video chats, to save me the trouble of driving across town when I’d rather stay home and grade. Finally, I’ve found better course management tools that save me hours a week. It all adds up. That’s time I can use for other work.

You might be amazed at how much time and energy you can free up just by troubleshooting and redesigning tedious tasks.

You’ll have to come up with tricks.

Few people can actually afford to quit their jobs to pursue their dreams. These days, even the “safe” jobs like teaching aren’t safe anymore. They come with plenty of their own risks and sacrifices. Now more than ever, it feels like if you don’t already have money, you’re f*cked.

Most of us have to pull over-time, just to keep food in the fridge. But that doesn’t mean you have to give up your aspirations.

It just means you have to go about them differently.

For example, let’s say you get 30 minutes of break at your shitty job. That’s half an hour you can put toward your goals before you start to feel tired. You can write an outline for a blog post on your phone, or the first draft of a poem. You can sneak off for a bathroom break here and there, and use 45 seconds to write down an idea.

Or let’s say you work at Starbucks, or a bar. You clock out. Your commute home will take 20 minutes. You know once the door to your apartment closes, that’s when the exhaustion kicks in.

So put in your earbuds, and stay there for 40 minutes to jump start whatever goals you need to complete. Finish them at home. Just getting something started in the time cracks of your day can make it easier to get yourself moving later. You build momentum.

Now that I have a kid, it’s harder to write like I used to. I can’t wait for her to fall asleep, or the next time she’s at daycare. But I’ve noticed something. If I put her in a sling and stay on my feet, she doesn’t fuss. So I’ve gotten good at standing up to write. I don’t need a fancy standing desk. I just cleared off one of my bookshelves.

Before that, I was having a rough time. A simple solution made the difference between writing and not. It wasn’t a motivation issue. Just a hack. If I were rich, I could hire a nanny. I’m not. So I have to be smart.

You’ll have to make painful choices.

Some of my grad school friends teased me for sleeping on air mattresses and yoga mats. “Do you even have a couch?” No, I was making a choice between furniture and books for my dissertation.

Most of them didn’t quite understand. Their dads paid their smartphone bills. And although mine helped as much as he could, he was limited. He made a nice salary, but most of it went toward my mom’s medical bills. Because insurance tends not to cover mysterious crazy.

Other tough choices involved my decision to delay starting a family. There was no way in hell I’d be able to raise a kid in a cramped apartment building, working 70 hours a week.

That would kill anyone, regardless of their motivation.

Even my frugality didn’t save me from student debt. You just can’t live on $18K a year when you’re giving part of it right back to your institution, and expected to spend about $3K on conferences and research materials. My actual net income was more like $12K.

This meant I had to take on debt, to the tune of $50K — which I’m still paying off. That’s why I get so irritated when talking heads and life coaches lecture millenials on their life choices.

When they say things like, “More money doesn’t matter.”

Or when they glamorize failure.

True, failure is necessary. But for many of us, the stakes of failure are sky high. Failure doesn’t just mean disappointment. We don’t have understanding parents to move back in with if things don’t work out. One failure could mean a lifetime of debt and regret that we can never escape.

The Problem with Aphorisms

Ironically, “seize the day” or “live every day like it’s your last” is the f*cking laziest advice you can give anyone. And yet it’s the first thing you’ll hear from someone who wants you to work harder.

Telling someone to “live every day like it’s your last” doesn’t help anyone with depression or a porn addiction.

It doesn’t help single moms, or college students working at Starbucks to pay for their textbooks.

In total honesty, I’ve watched my success accelerate on my way up the economic ladder. I worked my ass off in order to secure a good salary in the mid 50s. Once that happened, my life got easier.

My productivity improved when I acquired a washer and drier. It meant no more trips to the Laundromat, trying to read articles while someone’s kids shouted over arcade games.

A good salary has made it easier to pursue my goals. I did even better work, because I was more relaxed. I wasn’t having to tutor part-time anymore. Which meant more time to focus on my research — and eventually the ability to carve out some time for other aspirations.

Maybe success has nothing to do with your motivation, or fear of failure. You might just be poor. That doesn’t mean we have to settle for less, or buy into the advice that tricks white college girls into thinking they deserve a birthday weekend. It just calls for a different mindset.