It’s one week until Christmas (Merry Christmas!), and the last week of Advent is focused on love. The thing that comes to mind is how much I had a job I loved for nearly seven years at Indeed. It was one of the most significant losses I experienced when Indeed did its layoff. I wasn’t sure that I’d be able to find another role like it. I interviewed for some good companies and exciting roles, but ultimately none of them panned out, and none had the breadth of innovation I was hoping for. I’m sure I could have fallen in love with them had I gotten the offer and taken up the opportunity, but they didn’t look exactly right (at least from the outside). 

Contracting as a fractional CTO has been a steep learning curve, which I enjoy immensely. It has also come with challenges. Most notably, I miss working with my fantastic team from Indeed. We hired incredible people and gave them a lot of opportunities to lead how they saw fit, and it (generally) worked out well. Having the support of people who challenged, complemented, and questioned you makes for better products and a great workplace. I have good partners for my current contracts, but there’s something about it being temporary that has me wondering if they’re holding back.

Love Encouragement

I’ll start with a caveat. What little I know about dating is so outdated as to be useless. My wife and I met in High School, where we started dating, and we’ve been married for 22 years. So, this will not (intentionally) be dating advice, YMMV. That said, after countless books on love, marriage, raising kids, and more, the clear and consistent theme is that you don’t “find love” or “fall in love.” Even if you did, it’d be just as easy to “lose it” or “fall out of love.” You see, in the long term, love isn’t a feeling or a thing that happens; it’s a commitment, a decision.

This post in PyschCentral (6m read)talks about the four essential components of enduring relationships, which every job seeker (and many dating relationships) is looking for—attraction, connection, trust, and respect. I can see how, in my history of falling in love with companies and roles, I moved through each of those stages, and I can also see, in most cases, where those relationships eventually broke down.

I hope you find (or have already found) a company and role you love.

Loving too much

Sometimes, you drink too much of the Kool-Aid. I’ve been guilty of this. Having so much loyalty to the company and mission that you turn a blind eye to the changing culture and team around you. Every company evolves as it grows from zero to one, one to a million, a million to a billion. Any company that fails to evolve during that time would fail to succeed at the next level. Unfortunately, it’s like the adage about a frog in a pot of water. You either slowly boil, or you must stay awake to the temperature changes and decide when to get out.

The market is abnormal right now, so leaving is incredibly challenging for many people because it’s taking far longer to find their next role, but being ready to leave and leaving are two different things. Being ready to leave means you know it’s time, you’re extracting the last bits of learning, network, and expertise you can from that role before moving on. It’s all about making a plan, not just for where you’re going next, but for what you want to (legally) take with you.

A few quick tips on measuring the temperature of an organization and knowing when it’s time to leave. Ultimately, these are a gauge of the autonomy, mastery, and purpose that Daniel Pink points to in Drive:

1. If you find yourself less effective – you push for change but are nearly always met by more pushback than you can overcome.
2. You’re burning out – you put in more and more hours, but for little to no additional marginal gain.
3. You’re not gaining new skills – you’re always doing the same things and never learning new skills.
4. You’re no longer aligned with or believe in the purpose – you’ve lost your passion for your work.

Of course, plenty of other reasons go unstated here: you’re grossly underpaid, the work environment is toxic and much more. Depending on the severity, they might be reasons to leave immediately. Taking a regular assessment once or twice a year of how things are going is a simple temperature check. Having outside mentors and advisors you can connect with is another excellent way to look in the mirror and see what is happening.

Fun