Diary of a Job Search

Chicago, Illinois

I have never made it a secret that my biggest fear when I quit my job to travel was finding another job when I returned. While I will write more later about specific tips and what I think worked well in my job search, I thought I would share an inside look at how it actually all played out over the course of 14 weeks.

Week 1

It is the first week of October and my first full week back in the United States. It already feels like searching for a job is a full-time job in itself. I spend my mornings searching a variety of job boards, various LinkedIn groups and individual university job listings in Chicago. I am focusing on three areas: travel company jobs, fundraising positions with internationally-focused nonprofits and alumni relations/development jobs at universities. Including positions I applied for while I was still on the road, I have submitted applications for 19 jobs by the end of the week. I also send out emails to friends looking for networking assistance, outlining my three areas of focus. By Friday, I have already heard from someone through one contact to discuss a possible consulting opportunity, which gives me a nice boost of confidence.

Week 2

I apply for a couple more positions, including a tour consultant job with a luxury travel company (Job A). The job is listed in a LinkedIn group and I email my application to the person who posted it. She responds the next day, requesting a phone interview and I am ecstatic. It’s a travel job that on paper perfectly matches what I thought I wanted to do when I left on my trip. After an hour-long phone interview, we schedule a second phone interview for the next week.

I also hear from someone about a law school annual fund job (Job B) that I applied for back in early September, requesting a phone interview. I’m making progress!

Week 3

Monday morning starts with a bang as I have successful phone interviews for both Jobs A and B. I also apply for three more university jobs and set up some networking meetings in Chicago. Over the weekend, I speak with a friend of a friend in the travel industry and get a much better feel for options in that field.  I start feeling slightly pessimistic about Job A.

Week 4

I return to Chicago after three weeks in Minnesota. I send follow up emails regarding a few positions and I hear back from someone about a law school event planning position (Job C) immediately, requesting a phone interview. After a phone conversation, we set up an in-person meeting for Friday. Friday proves to be a busy day as I have a final in-person interview for Job A and the Job C interview.

I get an offer for Job A but am not too excited. I ask for a week to mull it over as my interview for Job B is the following Thursday.

Week 5

I have a half day interview for Job B, which seems to go well. I hear from someone about a position with a nonprofit (Job D), requesting an interview the following week. I hear from someone about an international alumni relations position at a university (Job E) and set up an interview for the following Monday.  I also hear back about Job B and set up a second interview for the following Wednesday. And, it gets even better as I hear from someone about an alumni relations job that would be based in San Francisco (Job F) – a former colleague alerted me to that one and they request a phone interview. Things seem to be moving full steam ahead and while I turn down Job A,  I’m getting excited that I may have a job in record time!

Week 6

Crazy busy interview week! Monday is a half day of meetings about Job E. Tuesday is a phone interview for Job F and an hour-long interview for Job D. Wednesday is a half day of meetings about Job B. I fly back to Minnesota Wednesday evening and then wait. I am told that finalists for Job E will be requested to come back for additional interviews the following week, so I book a flight back to Chicago for Monday morning to be on the safe side. However, by Friday I have heard nothing so I assume I’m eliminated – seriously disappointing because with the international aspect of the job, it was my first choice.

I get a call Thursday from someone about Job D, asking me to send references and salary requirements. They call again Friday telling me I am a finalist and asking me to confirm if I am okay with their proposed salary range, which is significantly lower than what I indicated my requirements were.  I don’t feel comfortable totally writing it off yet, so I ask for information benefits as well, hoping the benefits package might make up for the low salary.

I start freaking out a bit, wondering what I’ll do if Job D is my only offer and I don’t feel comfortable with the salary and don’t even know if I want to work there – I haven’t had a chance to meet any of the rest of the staff yet.

I hit the job boards again, something I have neglected the past couple weeks. I see a listing for a director of alumni relations at a law school (Job G), which is almost identical to my previous position and I see that it reports to a woman I know from my previous role. I email her and she responds immediately, saying she loves that I’m interested and suggests we talk Monday.

Week 7

I fly back to Chicago and speak with the woman I know about Job G Monday afternoon. We make plans for me to come in for an interview Wednesday afternoon. I also hear from someone about Job F and we set up an interview for Thursday afternoon. In the meantime, I decide to be honest about the fact that I simply need a higher salary for Job D, even if it means eliminating myself as a candidate.

Both interviews go well and I head back to Minnesota excited about my prospects. To top things off, I hear back about a director of alumni engagement position at a law school in Boston (Job H), inviting me for an in-person interview in the next few weeks.

I haven’t heard about Jobs B or E, so I email to follow up. Both confirm that they went with other candidates.


Week 8

It is Thanksgiving week, so I expect it to be quiet. On the contrary, I get a call from someone about Job B, telling me I did not get the job, but inviting me to apply for a major gift fundraising position (Job I), which has recently been posted. After giving it some thought, I decide it could be a good fit and apply. In the meantime, I make plans to return to Chicago after Thanksgiving for further interviews for Job G.

Week 9

Interviews for Job G on Monday go well, but my contact is out of town and says we’ll touch base on Thursday. In the meantime, I set up a phone interview for Job I, finalize plans to go to Boston to interview for Job H and set up final interviews for Job F – all the following week. I start to freak out again – the stress and constant movement is getting to me. I just want to stay in one place and know where I am going to be.

Week 10

The phone interview for Job I on Monday seems to go well, as do the series of meetings about Job F on Thursday. I should hear back about both the following week. But I still haven’t heard from Job G and I feel like that’s a really bad sign – I thought I was a shoo-in. I have a meltdown as I prepare to fly to Boston – what the heck am I going to do if none of these four remaining options work out? It could be months before I find something and right now I am not seeing a lot of other openings.  The Boston interviews go well, but they are planning on one more round and may not make an offer until the New Year.  At the same time, they ask me to let them know if I get any other offers.

Week 11

Still no word on Job G and I’m losing hope. I thought I would hear about Job I, but nothing from them either. On the other hand, I get invited back to Boston for final interviews for Job H. I get an offer for Job F, but start freaking out about the idea of moving to San Francisco – the salary just doesn’t seem high enough to make it worth moving to the most expensive city in the country. I have lunch with a contact at my alma mater and learn that they will be hiring soon – I throw my hat into the ring, but I suspect the timing may not work out.

Week 12

A whirlwind of interviews in Boston go well and I wind up the week with 2 job offers in hand – one for Job G and one for Job H. I officially turn down Job F in San Francisco. I email my contact about Job I as I realize that is really my top choice – I hope that if they know I have 2 other offers, it may push their hand a bit. In the meantime, I do phone interviews for 2 other positions that I applied for around Thanksgiving. Both want me to come in for in-person meetings after the holidays.

Week 13

It’s Christmas and I try to take the week off from thinking about the job search. I slowly accept that I won’t be getting an offer for Job I, my top choice, and I struggle between the pros and cons of Jobs G and H, as well as whether I want to return to Chicago or relocate to Boston.

Week 14

Finally, it’s over! After a lot of soul-searching, I realize it just doesn’t make sense for me to start over in Boston for a job that would ok, but not amazing. Chicago is home now and that’s where I want to be. I officially accept Job G and book a flight back to the Windy City!

13 thoughts on “Diary of a Job Search”

  1. How exciting to read this! I wasn’t always able to remember which job you meant in the post as there are many 🙂 but I am glad that finally you found what you were looking for and be in the city you wanted to be 🙂

  2. What a process! I admire your perseverence and energy throughout, not to mention your nice structured summary here. Congratulations. I’m enjoying your post-travel posts.

  3. Congrats with the job!
    You had quite some choices to make there. I don’t think a lot of people would’ve had that many options that could’ve resulted in actually getting the job.
    Hope you’re happy where you are now!

  4. I’m exhausted just reading this, Katie. But I’m glad it worked out in the end, and that you at least ended up back in Chicago where you want to be!

  5. Good for you! Your search was exhaustive and thorough and the rewards (although at times I am sure you were losing hope as indicated) will pay off. I love the way you really think things through. You obv had your ducks in a row and made the best decision for yourself. I also accepted a job position within my company but would not move without a raise. I am so glad things worked out for you.

    1. Thanks Rhona! I definitely think I did some things right in the process that led to me having multiple opportunities – even if I didn’t end up with my overall first choice job. 🙂

  6. The career counselor in me loves this post! Thanks for sharing your process, Katie. I know a few folks that will benefit from reading this.

    1. Thanks Heather! Stay tuned as I am working on a 3 part series with advice for job hunting – I definitely learned a lot in the process and I hope people can learn from my experience!

  7. Congrats on finding a job here in Chicago. I wish you nothing but success. It has been so much fun to follow your travels in the last year.

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