Match Making: A 30-Step Search

At the end of 2012, two major changes occurred in my life: 1) I quit the only salaried job I’d ever held, and 2) I ended the most serious relationship I’d been in. Both of those parts of my life had also started at the same time, and so beginning a new life in which neither was present was both freeing and disorienting. It was also really hard.

In the past four and a half years I’ve gone back and forth between loving the variety and loathing the instability of my day-to-day life. I have had dozens of jobs and amassed hundreds of connections. I have sat down to do my taxes in wonder and awe of the fact that I made it through another year. I sort of like being scrappy. I enjoy the unknown.

Still, at the end of the day what I want is commitment. To make it and to have it and to build toward something with substance and depth. I have searched for jobs and relationships, often at the same time, and after years of doing both I am convinced that they are essentially the same process. Those of you who have been there might know what I mean. Let me take you through one version of what it is like to go through that journey.


  1. You start the search process really super excited. There are so many apps and so many options. You only need one of them to work, which seems pretty much inevitable. After all, you are an amazing candidate with all of the right experience. Who wouldn’t want you?
  2. For each opportunity or profile that piques your interest, you imagine a potential future in which everything works out. You picture yourself in the office. You rehearse what you’ll say when you meet your future in-laws. You (hypothetically) spend your first paycheck before you even forward your resume.
  3. You set up personal profiles on several top websites (some of which your friends have sworn by). A quick scan of the aggregates shows that there are thousands of positions just waiting to be filled. You rely on fate and algorithms to lead you to the right one.
  4. At the start, you are exceedingly picky. You only apply for positions that you believe will be an ideal fit both now and in years to come. You do not consider the fact that both you and the role could evolve significantly.
  5. During your first couple of interviews (i.e. dates) you believe that your sheer enthusiasm and genuine self will be enough to win over the other party. You don’t even bother to do research beforehand. In fact, you are so sure of your success that you divulge information you later learn to withhold.
  6. After the first several options don’t quite pan out, you begin reading books about how to become a better candidate. Initially, you are grateful for all of this insight.
  7. You begin to realize that being “in between positions” is simultaneously freeing and terrifying. On the one hand you are not stuck in an undesirable situation. On the other, you want something (or someone) to hold to.
  8. After a smattering of applications, you get your first second interview. This one you prepare for. You wear your best clothing. You do your research ahead of time. You Google all keywords and scan all platforms. You rehearse your favorite stories. You hope they will work.
  9. They don’t.
  10. You try again.
  11. And again.
  12. The more often you interview and the more people you meet, the more those conversations all start to sound the same. (Let me tell you a little bit about myself: I was born in the Midwest and moved here four years ago…A time when I failed and had to reiterate? That’s a great question. There was this one time I was working on an article…)
  13. Each time a position doesn’t work out, you become less and less hopeful about any new prospect.
  14. Eventually, you quit.
  15. Then you start again.
  16. You go through binges of applying for every possible option and then forgetting to follow up. Eventually, you stop caring when they don’t follow up either.
  17. You decide to pray about your options. You realize you probably should have done this in the first place, but you didn’t think you would need to. You have since changed your mind.
  18. Everyone you know reassures you that this process of finding a “best fit” applies to both you and the other party. Still, you start to wonder if something is wrong with you when it repeatedly doesn’t work out.
  19. You begin to wonder how often this online match-making thing really works and realize you might be better off going through a friend or finding someone (anyone) who already has a personal connection and can vouch for you.
  20. You decide to “get offline” and begin to search more organically.
  21. You tell all of your connections (even those whom you’ve just met) that you are totally open and looking for new opportunities.
  22. You wait for one of them to respond, believing in fate and steering clear of the internet.
  23. You realize that what you know and who you know are equal barriers to getting what you want.
  24. You begin to begrudge the friends who effortlessly landed great positions straight out of college or within weeks of when they started looking.
  25. You resign yourself to the possibility that you might never find what you’re looking for. You feel like some combination of a failure and a hero.
  26. Throughout this process, you are frequently told that “it’s only a matter of time” before you find the right opportunity. At the start this sounded great, but as time goes by, you are not so sure.
  27. You witness one of your friends receive offer after offer, only to pass them up. Meanwhile, you widen your search to include fields in which you have no interest and positions for which you aren’t really qualified.
  28. You take interviews for positions for which you know you are overqualified and in which you’re certain you wouldn’t be satisfied. You are appalled when you do not get an offer.
  29. You come to hate any and all listicles that offer ten steps or seven secrets to getting what you want.
  30. When all seems hopeless, your one saving grace is that you know it could all change in an instant.


And that is how it is. Whether it takes two weeks or two years. Whether you find yourself back in a position you never thought you’d revisit, or signing your name to a contract that is all you’ve ever hoped for. One day the door opens and you haul whatever is left of you through it. You come out on the other side.

I’ve yet to find a human with whom I’m willing to co-sign a lifelong contract, but I have, finally, taken a job that requires a full-time commitment. This is what I’ve learned after a few weeks on the other side:

  1. Though the uncertainty is over once the contract is signed, you never stop feeling the pressure to prove yourself.
  2. The benefits that come from attaining employment—the healthcare and insurance, office parties, lunches, and occasional swag—are secondary to the fact that your search has ended. You can focus on investing instead of attaining.
  3. It is only after you have found a good fit—a position (or person) that suits you, challenges you, and appreciates all you can offer—that you realize they were hoping and searching and waiting for you just as much as you were for them.