Integrating back into the workforce after a failed startup attempt

Since quitting my startup attempt a few weeks ago, I’ve been taking my time to figure out my next steps. This has been extremely difficult for me to piece together. Integrating back into the workforce is tough.

Right now, my psyche is undergoing a rebirth. Previously, I completely reject the idea of employment and couldn’t not try to start a company for myself. Now, for the first time in two years, I’m seriously excited about being employed again. Previously, I only considered myself a developer and would only consider engineering roles. Now, I’m contemplating responsibilities beyond engineering for the first time since I became a developer.

Randomly applied to iDoneThis

I know Walter Chen, the CEO of iDoneThis. Walter tweeted that iDoneThis was looking for a content writer to drive their content marketing efforts.

I read the job post and was surprised by how awesome it sounded to me. Literally it was the first time I considered not being an engineer. Walter encouraged me to apply.

So I did. Suddenly, I found myself meeting iDoneThis’s CTO Rodrigo Guzman and discussing the possibility of getting paid for writing prose instead of code.

The one-month trial

iDoneThis’s interview process is essentially my ideal process as well. It’s a series of small work-relevant projects plus a straight-to-the-point chat, with both sides budgeted ample time to ask questions, followed finally by a one month freelancing trial before extending a full-time offer.

As somebody looking for a job, I particularly like to see a brief freelancing trial for several reasons. One is that I like knowing that my prospective colleagues were screened with a one month trial as well. Employers that are trigger happy with their job offers often end up building teams which don’t mesh and aren’t fun to work at. My current hypothesis is that a company who has a slower, more deliberate vetting process will be more fun and productive than the typical company that just does a few interviews and possibly a project or two before extending the full-time offer. I like knowing that my employers are much more certain about each hire that they make.

Another reason is that I don’t want to sign a full-time offer unless I’m more certain about the bosses, the company, and the work. Interviews can only communicate so much about the company. I’m far less cavalier than I was previously with dedicating my full-time work effort. My risk appetite for how I spend my time has plummeted to near zero, and I want every single week that I work for somebody else to be meaningful. A one-month trial helps me ensure mutual fit.

There’s always the risk of not receiving a full-time offer after completing a one-month trial for a company. To me, the risk is just the opportunity cost associated with no longer interviewing at other companies while you’re doing more interviews. You can abate this opportunity cost by continuing to apply for other roles. The company has yet to fully invest its resources in you, and in turn you should hesitate to fully invest your own time in the company. Really, that’s just logical and safer for both sides. Try your best during the one-month trial of course, as nothing but your best effort will help assess the fit, but take at least a moment every day to explore roles with other employers.

It might be hard to find the time to apply and interview elsewhere while you’re doing a one-month trial. However, the downside of not applying and interviewing concurrently means you incur the full opportunity cost. Nobody can tell you if that opportunity cost is worthwhile except you.

Not enough fit

iDoneThis and I started talking about doing a one-month trial with each other. The role was focused mostly on content writing. While I am excited about content marketing, enjoy writing, and think it’d be insanely, absurdly, immensely, wildly cool to earn money for writing, I personally had a hard time taking the compensation hit from my market wage as an engineer. Switching skillsets definitely made a dip in compensation reasonable and expected, but I didn’t feel comfortable taking too much of a dip.

Unwilling to compromise my pay rate, I wanted to expand the scope of my responsibilities to justify the compensation I expected. Unfortunately, this didn’t really work for iDoneThis. As Walter put it:

We want someone who wants to be the world’s greatest content marketer in the ~1 year time horizon. That doesn’t seem to align with what you want to do. Without someone who’s 100% amped to do it hardcore, we’re setting our content strategy up for failure.

Do I want to invest meaningful time to become a better content marketer? Yes.

Do I want to invest my most productive energies into becoming the world’s best content marketer, at the cost of not investing in other skills? No.

I immediately agreed with Walter: there wasn’t enough fit.

What do I want to do?

Walter also said something thought-provoking for me:

It seems to me that you’re still figuring out what you want to do.

Yes, I was still figuring out what I want to do. I went through iDoneThis’s entire vetting process, enjoying all the projects and interviews but ultimately not realizing that there wasn’t enough fit. The big lesson here is that I should know what I want to do before applying to jobs, or else I’ll waste everybody’s time.

The interview process with Walter and Rodrigo taught me some things about what I want in my next job:

  • Although I don’t want to do purely engineering anymore, I still want to code
  • I want my code to impact sales and marketing and directly increase revenues by bringing in new customers and reducing churn
  • The responsibility is something I’m excited to dedicate a year or two, at minimum, to master

Special thanks to Walter and Rodrigo of iDoneThis. I appreciate your time and your belief in my abilities. And because of the time these two spent reviewing my projects and chatting with me, I think I know what I want to do next now. I want to become a growth engineer.

If you enjoyed this post or would like to give me any feedback at all, I'd love to hear from you! You can tweet me at @dillonforrest or email me at It'd make me super happy to hear from you!