ASKED & ANSWERED is Vistaprint’s small business advice column – each week, experts answer questions from small business owners like you. Today, brand strategist Olivia Christian tackles your questions about standing out and staying motivated.

Taking risks

“You won’t know if it’s the perfect time to start until you start.”

Olivia Christian is a brand strategist and workshop lead – her ‘Own Your Story’ workshop has helped thousands of entrepreneurs share their small business stories.

As a Brand Partner at Vistaprint, we’ve asked her to share some of her best advice to recent brand questions.

You asked. Olivia answered.


I’ve been side hustling my life coaching business for 2+ years. With all the changes in the world, I feel like the universe is telling me to take the leap and pursue my business full-time. While I’m scared about losing a steady paycheck, I feel like if I don’t do it now, I never will. How do you know when to take the leap?


Couple things with this: first, losing a steady paycheck is a gigantic worry. In fact, if you weren’t worried I’d assume it’s because you have a cotton candy safety net held up by angels that sing ’90s R&B slow jams to put you to sleep…metaphorically speaking, of course.

Second, there’s a lot to factor in when making a decision to jump to full-time entrepreneurship. But one thing I encourage you not to do is expect there to be a perfect time! A better time, yes. But perfect doesn’t exist. If there’s one thing the pandemic has taught us it’s that you can plan your brains out but there are still things beyond your control.

Run the numbers and figure out how long you can survive without a sale or client. Have best case and worst case scenarios mapped out. Talk to your dependents, your partners and offspring and make sure they understand how your new life will impact your day-to-day…and theirs! And after all that planning and forecasting has been done, figure out how you’ll beat back the doubt and fear.

After all that is said and done…push play and expect to find out months (or even years!) later whether or not it was the PERFECT TIME!


Ready to take the leap? Check out advice from other entrepreneurs who took their side hustles full-time.


I messed up in a very public way on social media. Should ignore it and move on, or address it and beg forgiveness?


When I was in the 5th grade my mom bought me a pair of fake Keds sneakers and I freaked! The little blue logo on the back of that heel felt so important to me at the time. I wanted the real deal, and I cried thinking about having to wear those knock-offs. I had a certain design aesthetic that I had carefully crafted and those fake Keds were going to ruin everything.

Luckily for my savings account, I grew out of the need to rock certain labels. I didn’t, however, ever grow out the desire to be my authentic me. There were times when it was more difficult to do it or show it, but the need to be my true self has never wavered. And what attracts me to brands (and what attracts others to me and my brand) is authenticity. It’s all about being real, being honest about the good stuff and the hard stuff. Authenticity breeds loyalty.

The biggest brand fails occur when they aren’t honest – when they conceal, fail to take blame, or paint a rosy picture when the reality is chaos. Consumers cancel brands when those brands can’t be trusted.

On the flip side, consumers become loyalists – tried and true, ‘til death do us part kinda loyalists – when they feel connected and emotionally invested in a brand’s success.

I’m not saying you should put alllll of your business out in the street. I am saying, create opportunities to share the honesty of your small business journey with your customers. You will be rewarded for it!


Want to hear real-world stories of trials and tribulations from entrepreneurs just like you? Check out our Small Business Stories podcast for inspiration and advice.