Challenge yourself

by Jeff Hilimire on June 13, 2013


If I look back at my career its not too hard to see the different times that I was really challenged. There are few “jobs” that bring more challenges on a daily basis than being an entrepreneur. When you’re forging new ground and venturing into unchartered territory, with no roadmap to follow, challenges will abound.

But even in the last five years after selling my company to Engauge, where the business is no longer “mine” per se, there have been specific times when I was challenged by something that I had not experienced before. And tackling those issues was when I felt the most alive, the most passionate about what I was doing.

Tuesday I had two meetings with friends that are having a great time in their current positions due to the unique challenges the roles provide.

The first meeting was with a friend at a very large company in town. She’s been there for over a dozen years and recently took on a brand new role within the company. It’s her job to set the strategy, build the team and execute, with no blueprint or existing plan to follow. I’ve never seen her more energized even though she’s never done this particular thing before. And I’m so impressed that she took this position because when you’ve been at a large company for many years its easy to not take risks in order to preserve your job.

The second meeting was with another friend who took on a new role earlier this year that draws on her passion for art and music yet is not something she’s ever done before. And the responsibility is HUGE. She lit up as she toured me around her office, showing me the different things she needed to change. She also happens to work at a place with a long history in the city and a legacy that she’s been told more than once she shouldn’t “screw up”. Now that’s pressure!

I think we all need to make sure we’re challenging ourselves in our careers. Maybe not all the time, but without those challenges its easy to become complacent and “go through the motions”. Plus, challenging ourselves is the only way we truly grow.

So, how are you going to challenge yourself this year?

  • Vlad Gorenshteyn

    Challenges are awesome. Agreed. But when looking for your next gig/challenge, I believe it’s very important to find a company or endeavor where you are a) able to surround yourself with kick-ass talent to help execute your strategy, and b) enabled with tools and freedom to accomplish your goals.

    Falling into a situation where you don’t have these two things is an easy mistake to make. I’m sure others will agree. Oh and it doesn’t hurt if the product/service is something you’re super-passionate about, that’s paramount too.

    ~my two cents

  • Jeff Hilimire

    Vlad, good to hear from you again! 100% right, a) find your passion, b) figure out a place to go that will allow you to follow that passion and c) make sure its a kickass company.

    Then… if you don’t challenge yourself, you’ll regret your time there. But you are right, those things have to come first. Challenging yourself around a bunch of people you don’t like, or in a job you don’t have passion for, will not fulfill you.

  • Drew Hawkins

    I could resonate with the challenge of your first friend. I’m trying to create something completely new for the agency I’m at now. I can ask around and learn how different people have addressed challenges, there’s not really a blueprint for what I have to build here. At the end of the day, the way our agency serves and helps people is probably way different than the offerings of another one. Learning that we have to create our own way of doing things and that I won’t be given a to-do list – I have to make my own. It’s fun but totally scary at the same time.

  • Jeff Hilimire

    Awesome, thanks for sharing DH!

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