A blog that needs work

On the (job) road again: Of the long (job) road

I am not a fan of looking for work.

I've learned a lot about it, of course. It's always challenging though. Somehow, you need to distill who you are — as a professional, as a person, as a potential co-worker — into something significantly less than any of those things. To compound things, it always feels as though there is some serious imposter syndrome at work.

But I digress.

When Triggit was acquired, I found myself looking for work, again.

So what?

I had been at Triggit for a little less than a year before it was acquired. My professional life, up to this point, looked something like this:

  • 2014-06: Triggit (11 months)
  • 2012-03: Willet (2 years, 4 months)
  • 2010-10: Blue Coat Systems (1 year, 6 months)
  • 2010-04: Top Hat Monocle (5 months)
  • 2009-07: Desire2Learn (10 months)

As I graduated in April of 2009, that's not a great track record. That puts me at my 6th job in just under 6 years.

Admitedly, a lot of people take time to figure out where they fit in the grand scheme of things, and that can take some time at the beginning of someone's career. On the other hand, doing too much more of this can create a lot of anxiety (personally), and can appear that you are just job hopping. I would like to think that the reasons for my moves all make sense, but an employer might not see things so favourably.

It's not like I had really planned for a job search either. Searching for a job involves a lot of rejection, questioning your worth, a lot of failure and mistakes, and general fatigue.

Looking for my 6th job in such a short span of time was not encouraging, to say the least.

Fortunately, I have developed a lot of skills around the job search to make it a bit less of a grind. I should preface things by saying that the job search is a grind. If you're lucky, you can find something quickly, but I've found that the search is a weird mixture of your professional skills, luck, and timing.

What to look for

When doing your job search, you should know what it is that you are looking for. This sounds obvious, but if you don't know what you are looking for what you find may not turn out.

For example, here are some of the things I am looking for (some are not negotiable):

  • Company does good quality work: emphasis on tests, code quality, or engineering
  • Company does work that does good in the world: helps people at large or enables people to do things they couldn't previously
  • Local: I like where I live, so the company needs to be nearby, or allow remote
  • Small: Large companies tend to calcify towards change; I want to have a big impact, and that doesn't tend to happen in large organizations
  • Open, and communicative: No secrets, ideally, and there are reasons why things happen within the organization

The more specific your requirements, the easier it is to conduct the search. You can save time by avoiding certain opportunities, and focussing on the opportunities that you will be most interested in. Will you miss out on some things that could've worked out? Sure, but you'll never know either way.

In my case, I also have a specific set of companies that I would like to work for, so those are the ones that I start out with:

  • Mozilla
  • Github
  • Etsy
  • Shopify

Getting in touch

Knowing what you are interested in, the next step is to actually get in touch with these organizations. I could suggest that you go to their website, look up their available openings, and apply.

If I suggested that, I would be doing a disservice.

Applying to jobs sucks. Having been on the other side of the table, your application ends up in pile somewhere, compared by some arbitrary metrics, and only the lucky few are contacted. Some weird ritual of satisficing takes place. I mean, things can go well, it's just not good odds, is what I mean.

That's why I don't apply to jobs at all, for the most part.


It is way more effective when conducting a job search that you be a person. In as much as you are always a person, I mean to say that people should always think of you as you rather than a piece of a paper (i.e. your resume).

A good way to this is via networking and building up a relationship with recruiters, and people at different companies. There are tons of events to do this at, but oftentimes timing doesn't work out. In my case, I do a mediocre job of networking, so I don't have a huge group to go to.

I do leverage the network that I have, though. I hop on LinkedIn and see if I know anyone who knows anyone at the places I am interested in working at, and see if we can arrange to chat. I don't go looking for a job, I just want to talk with someone about their company, which is usually pretty effective.

Failing that, I take a similar approach, and send an email to any person who might be of help at the organization to try to learn more about the company, and connect with someone who might be responsible for hiring. For development jobs, this isn't too hard, as many people commit to open source projects and you can obtain contact information via their commit history.

In any case, in communication with these new people, I try to get across as much of me as possible. When sending out the initial email, I write it like I would with anyone else; that's not to say that I am unprofessional, but it is to say that I don't elevate the other person. Getting to some sort of face-to-face chat as quickly as possible is the goal.

That approach usually gives me a significant "in", and can tell me a lot about the company (and its openings) before I ever apply, which can save time. Sometimes I learn that there are no openings, or there won't be any for a few months, or what I thought might be a good fit is not actually a good fit.

Getting to interviews and following up

Most of the job search is about getting to the interview. I don't know what my success rate is in that regard (I have data, and will be talking about that another day) but I do know that most of the effort on the job search is spent outside the interview.

Getting to the interview is hard though. If you meet with people in person, to chat or to grab coffee, things tend to move quickly; you're a real person and there's a sense of urgency. If not, there's a lot of back-and-forth around scheduling and setting things up before potentially getting to an interview. Stay on top of this. It's not fun, but you need to follow up every three or four days to make sure the process is moving along. Companies are busy, and will rarely be the ones moving things along. That's up to you.

I don't really have any secrets around interviews. I study, like any other software developer does. I try not to elevate the other party; these people could be my peers, but even if I'm meeting a CEO, they are just people, like me.

One thing I keep in mind is to get across the idea that I am adaptable, not because it sounds good, but because it is true. The interview is the opportunity for me to learn more about the company, and for the company to learn about me. That often includes me getting across the point that I work best when everyone is open about things, and clear about things.

That's it?

I suppose it is. Then you will either have an offer, or find out a company isn't a fit, or get rejected. Then you do it all again until you find what you want.

A bit terse, I know. Sorry.

I've talked about the job search a bit in the past. Those posts might be helpful as well.

Next time, I will actually be digging in to the data I've collected, so instead of giving broad statements, I can (hopefully) provide real data around how I did (descriptively) and what appeared to be effective (I am not a statistician; this was not a statistical study).

Nicholas Terwoord

A self-titled software developer, "code archaeologist" (whatever that means), and professional geek. Spends too much of his time coming up with new projects, and not enough time working on them. Likes video games, board games, anime, manga, and Pathfinder / Dungeons and Dragons (GOTO: Line #1 - Geek).