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Five Things I Learned From Applying for 200+ Jobs

Five Things I Learned From Applying for 200+ Jobs

“That’s very brave of you,” he told me. We were sitting in The Heights Taproom, me and my squeeze. A group of rambunctious coworkers sat at the table adjacent to ours, having a celebratory holiday dinner and drinks.

He’s a soft-spoken person and at first I didn’t think I heard him correctly. I also have trouble concentrating in general when I am looking at his beautiful face. So of course I asked a deeply profound question: “What?”

“That’s very brave of you; most people wouldn’t do that. Most people give up.”

I was still confused. I grew up in New York City, a very expensive place to live in, even thirty years ago. Mine was a single parent household. I talked about bills with my parent as early as seven or eight years old.

My environment showed me the simple facts. Sh*t has to get done. Things have to be paid for. You have to apply to jobs until you get one. Other people may have other ways to live in an apartment with water, electricity, and food in the refrigerator, but we didn’t.

How is applying to 200+ jobs brave?

2017 was the toughest year of my life. I quit a toxic job in April, one that literally gave me nightmares and migraines and white hairs. My father died on June 23 of complications from throat cancer. My extended family live in the Orlando area, so not being able to pay rent found me sleeping on a living room couch by August 1st.

It’s an understatement to say I’ve done a lot of self-reflection this year. I’ve noticed a pattern of people (close friends, family members, coworkers, acquaintances) telling me I am confident, driven, and brave.

I never think of myself as any of those things until someone says it to me. Then I ponder…am I? I always think I am just being myself. Why do others perceive me as brave? Can I help anyone else become this way?

I don’t have answers, just perspective.

This post is entirely subjective. And I acknowledge that my U.S. citizenship, three advanced degrees, ten years of work experience, etc. are factors that play into my job history and my experiences with applying.

However, I hope reading my story helps bring your mind to a bird's eye view. At that height, you can see the full picture. There are some things you could improve (your résumé, your interview skills, etc.).

But there are many ingredients that go into the job applying pot. I think the chances are equal the reason you haven’t found one yet is not just you, it’s the entire HR process.

[Related: Time is Up on Staying Blissfully Ignorant]

1) Job applying is lonely work.

This year I frequently heard/read that it’s normal for a job search in the U.S. to take 4–6 months. Literally you are in an apartment, a bedroom, a local Starbucks by yourself for weeks on end. You miss birthday dinners and summer blockbusters because you have $3.76 in your bank account (and don’t think it’s a good idea to incur credit card debt when you have no income just to see Wonder Woman on a large screen).

If you do show up for a shindig or a night out, your loving, well-meaning friends pay for your meal or your ticket. And the more they spend on you, the worse you feel, so you stop going. There’s also this magical thing that happens week after week where everyone you know is getting a new job but you.

This is normal and you surely have read about it elsewhere. But what I’m talking about here is the fact that many people who you think will really help you out, put in a good word with their boss, introduce you to their colleagues, etc. just don’t.

Of the tens who said they would—people I’ve known for years, the most encouraging people—only a couple actually did so. People have good intentions, but they’re busy. Mentally prepare yourself for this reality; don’t internalize it or view people negatively.

Bravely ask for help more than once or even twice, or ask a longer list of people.

2) Interviewers are subjective.

Anyone who talks like they aren’t is lying. Every office has politics. It’s human.

Organizational history you don’t know about holds a lot of weight in your future prospects. You can very well end up paying the price for mistakes others have made, be they prior hires who have already been fired or those who still work at the company.

I had the best interview of my life with the person who would have been my boss for a dream position at a famous global corporation that earns billions in annual revenue. The person, the company, the role felt like I found my soul mate.

The next video interview was with the boss’s boss. Despite understanding my qualifications, this individual did not get a feel for my personality. Hence, the person was not convinced I would be a good fit. This was particularly worrisome due to a recent bad fit (the reason the position was open in the first place).

I was immediately cut from the roster. My choices were to cry about it or take it as an indication of my awesomeness. I made it to the third interview of four with a company of that caliber! I didn’t throw a party, but I did pat myself on the back and dance it out.

Bravely choose to celebrate yourself despite being continually rejected.

3) People will waste your time.

With no shame or remorse. Their main concern is solving their own problem. Doesn’t make them evil, just human. One person courted me for a month, saying a new position would open up soon. This person even e-mailed me the job description for my review so as to tailor the role to my skill set.

After four weeks and about a hundred emails the person finally told me the salary. It was $30K less than I make now. Given my résumé and our long, detailed back-and-forth conversation, I don’t know how the person thought I would or could accept the pay. Perhaps the person knew it was very unlikely, which is why that bit of info was held to the end.

Another person exchanged just as many e-mails with me for a round one phone interview that didn’t happen until a full month after the first e-mail. This person rescheduled the call two, maybe three times. Then suddenly (conveniently?) the position was cut and no one was hired. (In the following weeks, I saw the position reposted. Who knows what was going on there.)

Around the same time I interviewed with a third person at a worldwide intergovernmental organization. The interviewer could not possibly have shown less interest during our call. I heard children playing loudly in the background (breaking basic phone interview etiquette). The only reply to every one of my well thought out answers was, “Thanks for that,” then on to the next question.

At the end the person rushed off the call (that was less than 30 minutes) saying there were a lot of other calls to make and without giving me a chance to ask any of my own questions. My first conclusion was that the person was just going through the obligatory HR motions. Clearly someone not me had already been picked out. But then I realized, if by some slim chance I did get the position, this person would have been my boss.

I withdrew my application. Deep down I knew if the person was disinterested and inconsiderate during interviews, the person could be a disinterested, inconsiderate boss. It would only cause me to be applying yet again at the same time next year.

Bravely say no when your gut tells you that something just isn’t right.

[Related: Four Signs That it Might Be Time to Quit Your Job]

4) You may need to switch fields.

Notice I didn’t say disciplines. If you have invested thousands upon thousands in your degree and most of your work experience is in a certain role, don’t switch.

What I mean is, if you’re a graphic designer at a boutique agency, you may need to apply for graphic design roles in academia instead, depending on where you live or if you’re willing to move. If you are really good at selling health insurance, maybe you should try to figure out how to apply your skills to selling cars.

I can’t say much on this because transferable blogging and social media skills can be very straightforward to present. What I can say is I didn’t discover marketing until I took a 101 class during my grad program at NYU. I fell in love and took a marketing internship at TIME Magazine. And for the next seven years I ran in the other direction of corporate America.

The marketing honeymoon was over and I never worked for a marketing company or in a real marketing department until now. The people I worked with at TIME were wonderful; no Devil Wears Prada saga. But I just got the overwhelming sense that big money was the sole goal.

After all my nonprofit years, I had to accept mission-driven careers have largely become a luxury. I do not have a spouse whose income complements a nonprofit salary. My children’s names are Sallie and Perkins.

My luxury in life is I don't have to work to death just to “make a living.” I stopped applying to nonprofits, and I’m now at a small B2B that pays me what I know I am worth. They also have a lot of heart, engage in company-wide community service, and treat employees like people. They are a fourteen-year partner of the EPA, take measures to reduce or eliminate waste, and keep an eye on our company’s impact.

We’re not saving the polar bears or building the future of diplomacy. But I feel more fulfillment than ever because I’m truly in my element for the first time. This does exist! And I know I only found it because I held out for it.

Bravely hold out for your true fit and don’t let people call it an ideal.

5) Be willing to do what others won’t.

You likely have also heard or read this a million times, but here’s what it means specific to applying for more than 200 jobs in one year.

Sum total, I did literally everything people advise you to do. Networking events (where everyone else was looking for a job, too, and it was so loud in the bar you could barely hear the other person speak). Informational interviews (where people said they would contact me and never did). Job fairs (where most attendees were ten years younger than me and half the jobs were farther than I would be able to commute).

I consistently asked personal and professional contacts to review my résumé and cover letter. I asked interviewees why I didn’t get the job and journaled their responses. I even self-designed personal business cards that match my résumé (thanks, Canva!) and printed 500 for $5 at Staples. I signed up with five different recruiting/staffing companies. And that’s how I got where I am now.

One afternoon a recruiter called me up and said there was an open position proving difficult to fill since it was only a six-week contract. Seems no one else wanted to interview for it. I had never heard of the company, but I knew I could do the job and I had nothing to lose.

My amazing new boss had a set number of people on the team organization chart and that number didn’t include me. Yet by week six, I had an offer of full time permanent employment. Did I know this was going to happen? No. Could it have happened if I had not been willing to contract for six weeks? No.

Bravely take the narrow road; it will get you to places others never find.

Bonus lesson.

I suspected the whole time that applicant tracking systems are awful and counterproductive. They can actually prevent good hires from happening (no offense to iCIMS, Taleo, and all the rest). But the proof is in the pudding. My pudding is LinkedIn.

Of the many recruiters who have been contacting me almost daily since I accepted my current position, one of them was from an organization I had applied to! Don’t let a bad system make you feel like a bad candidate. I told the person I would have loved to join their team when I was available, but now I am solidly off the market.

Moral of this story? If you’re going through hell, keep going. Never give up.

[Related: 3 Things Women Can Do To Win The Future Of Work]


Vanessa Correa builds brand identity through creative exploration and solid architecture. Using her innate strengths, educational background, and diverse professional experiences, she markets brands with effective strategy that creates ambassadors.

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Community Discussion
Radesha (Desh) Dixon

Nicely written.

February 12, 2020