Why contracting is the worst

When I left Hired in April 2017, I wasn't sure what was next for me. I knew the last 2 years had been hard on my family and me and I was hopeful that the next 2 years would be better. What I experienced was almost a mirror image - the things I hated about Hired would go away; the things I loved about Hired would become my challenges.

First off, in terms of actual career satisfaction, contracting is the worst. Yes, I know of certain design and engineering folks out there who make a great living, holed up in a mountain town, loving their flexible lifestyle, but I don't believe that is an achievable reality for most professionals or, at least, that was not my experience.

What I experienced was weekly evaluation of whether I was worthy or not. I felt a general lack of belonging and was never ever part of the team I was supporting. I experienced building something from scratch and then having to build again, and again, and again. I had to make project decisions that were not always aligned with the long term goals of the company; do I prove my worth and get short term gains or do I build something good, that lasts. It was all of this that made each contracting assignment deeply unsatisfying.

It wasn't all bad. I did have control over my schedule - and with a little kid in the house, that was something I valued immensely. I got to take my daughter to swim lessons on Friday's, while I made up time late at night (some of my best Salesforce Development hours were past midnight). I got to learn about a lot of different organizations - the good, the bad the ugly - and often as an "external" I received more candor than I would expect coming in as a managing executive.

I did make some real change. I helped a few folks along the way which I am proud of. I learned a lot. I grew personally in the way I manage stress and my relationship with my wife got stronger and more collaborative. I also started figuring out what I want to do next.

Although the mirror image was tough, it was what I needed. When I embarked on this two-year contracting voyage I got the same piece of advice from several people: Take your time.

This would be the same advice I'd share with any exiting employee leaving their long-term, high intensity gig and here's why: You need to reflect. You need distance. You need answers. All of those things are near impossible to come by in the weeks after leaving a gig. It takes months to fully internalize everything you experienced and listen to yourself vs the objectives of the organization.

For that, I'd say take your time. Do some contracting. Feel the separation of self from an organization. Re-constitute; so the next move is the right one. I'd also add:

  1. Get paid upfront
  2. You will feel unsuccessful. Its probably not you, but the situation
  3. Take every meeting you can
  4. Even if you don't have to, if you can: Go onsite a few times. It will make your life easier
  5. Low ball your goals - you don't know what you're walking into

It was hard and I'm glad I'm through it and I would do it all over again. I needed to contract and now I'm ready for my next tour.

Trent Krupp

VP of Operations at Triplebyte. Founded an agency in my 20's, sold it to Hired and became employee 5. Recruited for Atomic (VC), Credit Sesame and MakerSights. Helped the founders of recruitment tech startups Shift.org, Terminal and Beacon in the early days.

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