Five Ways to Challenge Yourself as a Business Owner

Aisle Planner How to Challenge Yourself as a Business Owner
Photo courtesy of LVL Academy and Brian Leahy Photography

As small business owners and planners, embracing challenge is something we have to learn to do in order to become our most successful selves. We have no choice but to deal with unexpected challenges all of the time — last-minute mind-changes, cancelled meetings and inclement weather are all just part of the gig. But, the great part about being a business owner is that we also get to choose challenges for ourselves — ones that we can control and learn to embrace. Ones that make us better, stronger, more sharp. Today, then, we wanted to break down five positive ways you can challenge yourself as a business owner.

Allow Others In

A strong sense of ownership is great as a business owner, but it’s also important to understand that you can’t do it all alone. Though it may be challenging and uncomfortable, oftentimes the best way to grow is to allow others in. Hire help if you’re feeling overworked (try a virtual assistant) if you’re not ready to commit to bringing on a full-time team member) or bring on an intern to mentor for a fresh vibe in the office.

Allowing others in also means allowing in outside feedback from industry insiders. Meet up with other planners, get together with marketing professionals, or go for coffee with vendors. Challenge yourself to allow others in once a month–whether that’s in the form of bringing on another set of hands for help one day or simply sitting down for drinks with that favorite graphic designer of yours.

Continue Your Education

Another great way to challenge ourselves as business owners is to take a class, sit in on a webinar or attend a conference. We’re so (SO) busy and, oftentimes, simply just don’t have the energy for extracurriculars, but a good course or creative conference will pay for itself tenfold. You’ll walk away feeling refreshed and reenergized and will likely have a whole new list of industry connections. Challenge yourself to take at least one course/tutorial/webinar or attend one conference each year.

Give Back

Giving back is one of our all-time favorite ways to challenge ourselves as business owners. The key is to do something that requires your presence–don’t just write a check; challenge yourself to be physically present in some form of a philanthropic effort. Maybe you bring a group of young women to your studio and show them the wedding-planning ropes. Maybe you head out and serve the homeless on a night off. Maybe you help a friend’s daughter with her résumé. Whatever you do, give it your full attention for that short period of time and allow yourself to be fully present. As planners, our schedules are super tight, but if you can make room 1-2 times each year to do some hands-on good for your community, you’ll feel refreshed and happy.


Team-building is one of those phrases that people hear and automatically roll their eyes at, and understandably so. But we’re not talking about attending a cheesy team-building course or falling back into each other’s arms to build trust. Instead, make team building work for you.

Maybe that means that every time your team achieves something great, you take them out and talk about the success (and how to recreate it) over cocktails. Maybe you take your all-female team for manis and pedis on a quiet afternoon. Maybe you paint the office walls together one day. Whatever the case may be, team building should be less about contrived group activities and more about doing things that truly, organically bring you closer as a whole. Challenge yourself to setup some form of team-building activity–however short and sweet–at least once every other month.

Set Goals

We could go on for days about setting goals (and we have here, in fact), but the bottom line is that, as business owners, we should all have a set of clear-cut, measurable, attainable goals as part of our business plan at any given time. Rather than just telling yourself, “This year, I’d like to plan 10 weddings,” hold yourself accountable and make your goals specific, actionable ones. Write them down and map out a clear path for achieving each.

Challenge yourself to have a set of overarching goals for the year (redesigning your website, placing digital ads, bringing on more clients, etc.), and smaller goals for each month (cleaning out that filing cabinet, decluttering your inbox, posting blogs, etc.). And, most importantly, challenge yourself to hold yourself completely accountable for those goals.

Overall, there are so many positive and productive ways to challenge ourselves as business owners. These are our five favorites, but we’d love to hear more from you. In what ways do you challenge yourself to keep those skills oh-so sharp? Share your thoughts with us in the comments section below.

About the Author

Gillian Griffith
Gillian Griffith

Gillian knows there’s nothing as deadly as a woman with good grammar, great nails and a strong backhand (think: tennis). She is based out of Las Vegas, Nevada, where she spends the sunny days with her family, her Louisiana Catahoula pup and, her ultimate love, a 1939 typewriter.

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