I have tried to train myself to view feeling comfortable in my job as a big warning sign. The flashing red lights start going off when I catch myself thinking, “You know, I’m actually pretty good at this.” Hubris is a dangerous thing that leaves us blinded to reality. It feels great, but it’s a dangerous place to be.

It was bicycling that tipped me off to the dangers and often re-reminds me of it:

A couple of times a year, I’ll be out on my road bike pedaling along and just be flying. Beautiful day, landscape rolling past, feeling great, and thinking I’m in much better shape than I thought. Then I’ll turn around to head home and realize that I had a strong tailwind. I wasn’t in great shape, I just didn’t notice how much I was being helped along.

I regularly mountain bike on a pretty challenging set of trails and it’s easy to start thinking I’m pretty good. Well, no. I just know my trails really well and that’s very different from being good. I recently rode a different set of trails and got my hiney kicked. Turns out I’m not quite as good, fast, or strong as I fooled myself into thinking. A painful lesson, but necessary.

Success is the product of good thinking and hard working. It’s important to celebrate our accomplishments, but it’s easy to over-congratulate ourselves for our successes. Yes, we have quite a bit to do with our triumphs, but sometimes they are helped by additional factors that we don’t notice and can’t control. The tailwind, familiarity, being a big fish in a small pond, a lack of real competition, staying within our comfort zones all help us think we’re doing better than we actually are.

Consider some of the key places we see this show up:

People often have a hard time making the jump to the next level of whatever they’re good at. For example, athletes who are superstars at the regional level, are just another decent player at the national level. Another example is MBA programs, where people who were the standouts as undergrads are just another face in the crowd, surrounded by lots of equally smart, aggressive, and talented people. That’s a humbling experience. Some relish the challenge and love being surrounded by people who push them to bring out their best. Others struggle to come to terms with the idea that they are just average in their new peer group.

When hiring, how do you determine that an applicant’s previous successes will translate to your company? We’ve probably all seen people with impressive resumes not do well because the new environment was too different and didn’t mesh.

Or what about the rising star employees who flame out when they are promoted too soon. They show some promise, have some early successes, and then get pushed to a level they are not yet ready for. Something unexpected happens that they don’t have the experience or luck to deal with and it all caves in. Worse, they start believing their own hype and because of their past successes they are given a lot of rope to hang themselves. When it all catches up with them it catches up hard.

This is also an issue with employee development: how do you develop people fast enough to keep them engaged, but slow enough that they can really,  truly learn what they need to know? How do you acknowledge and applaud them without instilling a false sense of confidence?

In our own jobs, we want continuous and never-ending improvement, but how do we push ourselves beyond our comfort levels when it’s so, well, uncomfortable? We want success, but easy success fool us into thinking we’re better than we are. If we don’t consciously try new things, experiment, and sometimes feel like we’re failing, it can prevent the growth that leads to bigger, long-term success.

Where are you feeling confident in your job? What would you need to do to make your job feel challenging? Where is the edge of your skills and what can you attempt that is slightly beyond the boundary? What new settings, projects, or tasks can you take on that might push you just a bit?