3: You are the only one that will hold yourself back

For two years at Square I felt sorry for myself. I was in a job I didn’t want to be in and wasn’t moving up in any significant way. I had every excuse in the book for why I was being held back — I didn’t have the experience and the hiring manager didn’t like me and I was too young. At some point I realized I was doing a lot of complaining without doing much about it.

If you really want to move into a new role, just start doing it! Obviously you need to do a great job at your core work (never lose sight of what you’re being paid to do) but once that’s completed, start working on what it is you’re passionate about. You will be working two jobs and you’ll surely work nights and weekends. But if you’re truly passionate about this work, you won’t mind. In fact, you’ll feel better about things because you’ll be moving in the direction you want to be headed.

I was on the Chargebacks team but wanted to be in Sales — bringing Square to all the awesome small businesses around us. Selling Square was how I got my foot into the door originally and where my true passion lied. But we didn’t have a Sales team at the time and had a history of being against the idea of ever needing one. A friend and I set out to change this. We worked nights and weekends putting a project proposal together and went on a roadshow internally to get support for the idea.

The plan was this — we would get our day jobs done but in our free time we would sign up the next twenty multi-location, cool, hip, Blue Bottle-like businesses across the country. The only cost would be our travel, which would be limited because we had day jobs. Otherwise, we’d be bringing in Square’s next group of marquee merchants for free. Who would say no to that offer?

The project was a success and ultimately led to me moving off of Chargebacks and onto the Business team, where we started Square’s first ever Sales team.

It comes down to something Chris Sacca talks a lot about — providing value before you ever ask for it. There’s one approach where you can say “this is the new role that I want and here’s why I deserve it.” At that point, you’re pretty much just hoping something works in your favor. The other approach would be to actually get your hands dirty and do the job before it’s given to you, so that in the end, there’s no decision to be made. You are clearly the right person for the job.

Even if you don’t want to change teams, there’s a ton of ways to increase your responsibility and ultimately, move up on your current team. Look at your workflow today. Where are the inefficiencies? What opportunities are you overlooking? If you identify these gaps, come up with a solution, and do some of the work upfront, I guarantee your boss will listen.

If gaps exist on your team today, it’s likely that no one owns it. You can own it! As long as I was getting my core work done, I was never shot down for wanting to take on more. And with each task I took on, the more trust I earned across the company and more responsibility I was given.

Again, the work and the opportunities are out there. You are the only one that will hold yourself back.