The Pit of Despair

Everyone knows that the best time to go job hunting is from a position of high leverage-already having a nice job, getting headhunted, and having money in the bank all help immensely.

This past fall, I found myself with none of the above.  A corporate restructuring (yes, startups have them too) had alienated and pushed out several more recent positions at the company I had been working with, and I was one of them.  #startuplife.

As is often the case during exciting times, I sat down and opened up my laptop.

Pimp out the old LinkedIn, check.  Redesign my portfolio site, check check.  Send a few messages to some people I knew- check, check and  check.

Now, with grief and existential crisis successfully pushed from on top of me to the wings of my mental periphery, I settled into what seemed like the best thing to do at the time- the arduous process of searching for and filling out job applications.

Two months of 10 hour days later, I was about to rip my hair out.

Some lukewarm interviews and the feeling of betrayal stemming from not getting called for positions I’d be perfect for was wearing me down.  Most tasks have an obvious way forward and way-markers to note progress. But this seemed like a tall, solid wall.  I was stuck.

Once you apply for all the jobs in your field, you begin to realize that good jobs are few and far between, and checking the same job boards daily is an exercise in ego-destroying futility.

The Light

There was a startup I knew about that had recently raised some money, and I had been very interested in them.  In fact, I’d applied (to no avail) to positions outside my field in hopes of just getting on board.  Armed with a real will, I figured out the CEO’s email and shot him a quick message.  It went *kind of* like this:

Hey soandso,Congrats on raising money, I’m really excited about what you’re doing.  Here’s a cool resource I found that might be of some help on your journey.  *link*

By the way- I couldn’t help but notice suchandsuch and suchandsuch about your website.  You could probably get more thisandthat and thisandthat by doing tweaktweak here and a tweaktweak there.  I’d bet that that would significantly help raise tweedledede and lower the cost of tweedlededum.

Anyway, all the best.Colin

I didn’t hear back, time moved on, and I moved backwards to filling applications again, thinking this was the practical route to a responsible employment situation.  All this is ironic, because:

A full eleven days later, this gem drops in my inbox.

Hey Colin,Thanks for reaching out!  Seems like you really know your suchandsuch stuff.  Can we jump on a call to talk this out?


Well hey there. This was interesting.

We had the meeting.

I took what we talked about and hacked together a prototype and sent it back that day.

They then alerted me that they’d created a new position (that hadn’t existed before) and two weeks later, I had a new job with a company I was really excited about doing exactly what I wanted to be doing.

Keep in mind that in those two months, this was the only email I sent directly to a CEO of a company I really wanted to work with.  

What was different then, you ask?

The Takeaways

There are a few here, and I may draw a bit too much general wisdom from a specific incidence, but fuck it, this is my blog and I’ll do what I want to.

Alignment.I made it as clear as I could how much the vision and ethos of the company resonated with me. I tried to put myself on their side without doubt.

Usefulness.I think I could have gotten away without the link, but the key was putting a finger on something that I clearly demonstrated could be better and demonstrating immediately after that I would be a great person to fix this particular problem.

Tact.I would have probably eventually driven the conversation to job prospects had he just responded and said “Thanks!” As it happens, the best possible scenario happened in that he brought it up first. However, it was by design that I asked nothing initially. I really did want to help, and adding a self-serving request to the end of it would have turned a nice connection into a transactional (or worse, manipulative) feeling interaction.

Follow Through.I’m sure I didn’t have to put a prototype together that day (in fact, he even told me so), but I did it anyway. My reasoning was this- if I could add “He follows through strongly and quickly” to someone’s internal schema of me, along side “He’s on our side” and “He’s useful”, I’ll do it every time.  If being too good is the only thing to count against you, just take that one on the chin.

So, after two months of slogging, repeating myself, and more or less begging turned up nothing at all. Then, I spent ten minutes on an email and ended up with a situation literally twice as good as what I hoped for in the first place.

If I ever end up in this situation again, my plan is this:

  1. Resist the urge and stop filling out job applications.
  2. Make list of ten companies I really like and want to work for.
  3. Email the best person (may be the CEO, but probably not in a larger company) and offer as much value as I can, preferably in my area of expertise.
  4. See what happens.
  5. Repeat.
  6. Pimp out the old LinkedIn, redesign my portfolio site, send a few messages to some people I know- check, check and  check.

Let me know how it goes. There’s always something better out there.