Sail Away



Finally. It took me awhile to get here, but this is where the rubber really meets the road. After a lot of talking and reflecting, it feels great to finally be making tangible progress job searching in the more “traditional” sense. Applications, here I come!

Though I’m no amateur. I’ve heard about the “black hole” of the online application process and the horror stories of job seekers spending months tailoring several hundred versions of resumes—generating different versions for every possible iteration of an online posting. I decided early on that that’s not going to be me.

I explicitly focus on quality—not quantity—of opportunities. I pick a handful that seem both interesting and obtainable and do everything I can to get a foot in the door through a current employee or reference. I know the numbers game isn’t in my favor—the key is changing the odds around for a handful of opportunities. While I do allow myself a few completely random online resume drops, I generally assume I won’t hear back from them.

For the handful of opportunities I do care about, I treat them like a detective would a case. I uncover how my network leads me to someone close to the new position (LinkedIn can be great for this). I get advice from knowledgeable old-colleagues and acquaintances about the opportunity. I seek out a friend or freelancer to edit my cover letters to avoid that one stupid, fatal grammar flaw. I leverage some online tools to get around those new applicant tracking systems that all companies seem to use nowadays. Above all, I do my best to distance myself emotionally. If it comes through, great. If not, I’m moving on!

Even though my days feel busier, I’m trying to remind myself that screen time isn’t everything. I refuse to give up the healthy habits I worked hard to establish. Even now, while I’m at this in earnest, my life outside of the job search goes on.


  • Focusing on quality of application efforts, as opposed to quantity

  • Prioritizing human-to-human connection over online “pre-interview” work

  • Engaging resources to ensure application materials are error-free and optimized

Chris Rudnicki