It's hard to leave a good thing

by Dale Davidson March 18, 2026

It's hard to leave a good thing.

My wife and I had decided to move to Portland, and then at the last minute (well, last few months), decided to extend our time here in DC by six months.

One "rational" reason to stay was to take advantage of our health care network for the birth of our second kiddo in August.

But really I think all the fears about losing our career options, friends, and social network bubbled to the surface.

These are real concerns.

But in considering those fears, we downplayed the risk of staying.

We could be stagnant in our careers, our friends could leave, and most importantly we'd lose the opportunity to build the relationship with her family that was our entire reason for leaving.

This is called "status quo bias."

"Simply put, the status quo is the path you’re already on or the way you’ve always done things. The bias is that we have a preference to stick with those decisions, methods, and paths that we’ve already set upon, and a resistance to veering from them into something new or different."

Duke, Annie. Quit: The Power of Knowing When to Walk Away

"The status quo represents a mental account that we already have open, which has sunk costs associated with it, the time, money, or effort that has already been put into the way we’ve been doing things. Closing that account by switching to a new option can make us feel like we are wasting those resources we have already spent.

We also become endowed to the status quo, taking ownership of the decisions that have kept us in that groove and anything we have created along the way.

Another of the factors that cause us to hew to the status quo is an asymmetry in the way we experience loss aversion. We are much more bothered by the downside potential of changing course than we are by the downside potential of staying on the path we’re already on."

Duke, Annie. Quit: The Power of Knowing When to Walk Away

In my book, I spend a lot of time talking about both the pros AND the cons of going 1099, to give you a holistic way of determining whether going 1099 is right for you.

But, I didn't mention that there are cons to staying in your W2 job.

You might make less money, get stuck with a sucky boss or project, or get laid off.

You could just be generally unhappy because you didn't make a change.

So when considering the decision to go 1099, make sure you include the pros AND cons of staying in your W2 job.

Only then can you make an informed decision about striking out on your own.

Want the full playbook? Check out Going 1099.