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How to Overcome Challenges Like a Boss

It’s not the mountain’s height that holds us back from seeing beauty from the top, but the fear that we’re not strong enough to climb it. It’s been exactly five months since the day I took the leap to become a business owner and take my blog fulltime. I can’t tell you I’ve reached the top of the mountain yet or the hike is easy, but I’ve learned so many lessons climbing from the person I was to the person I want to be. Thanks to encouragement from my friends at Olay, I feel empowered enough to share some of my lessons learned in overcoming fear to start a business and become be a total boss.

8 Ways to Overcome Challenges in Business

Dress // Shoes (similar) // Sunglasses // Bag (similar) // Watch 

Take a Look at Where You Are

I’ll never forget the first time I truly considered taking the leap to make this blog fulltime. I was at my company’s off-site leadership meeting when my boss asked us to each make a timeline of our lives. From birth to the very end, we mapped out what achievements happened in our life and which ones would come. While I’ll my coworkers wrote down their plans to climb the ladder, I noticed tears were falling onto my paper without really realizing why. I realized I was dealing with the reckoning that rather than a sturdy ladder to climb, my heart really wanted a mountain to explore.

In this very moment, what’s on your timeline? Be bold, be imaginative, and don’t hold your pen back or pause. The words you write first might catch you off guard.

Forget the Lies You Tell Yourself

As a business owner and fulltime blogger, I catch myself questioning my authority and experience more often than I’d like to admit. When I finally left my day job to pursue my blog, I had far more time to let the lies we all tell ourselves pollute my headspace. Here are a few of mine:

“I’m not pretty or skinny enough to succeed in a job that thrives on photos”

“I don’t fit in with my blogging peers who each have a tribe of their own”

“I started too late”

“I don’t have the drive to make this a business”

“There’s no market for average looking girls who have a lot to say”

“No one cares about my message”

I’m dragging all of my skeletons out of the closet to call them what they are: lies. It’s human nature to have doubts about ourselves. Categorizing toxic thoughts as false stabs at your confidence will help you see they are simply thoughts that have no control over your success.

Cup of Charisma Wearing Esme Pink Floral Dress Gal Meets Glam Collection 6

Quit the Comparison Game

Bloggers live on social media, and I won’t sugar coat it: social media can be dangerous if taken too seriously. By comparing ourselves to the Instagram models of the world, we start to weaken our own perception of self-love. The more time I spent looking at follower count, engagement, and the appearance of others, the more I began to question and compare myself.

There will always be someone who is further ahead than you, just like there will always be someone behind you. When others bloggers succeed, it means our industry is thriving. The best news I can tell you about any creative industry is that there is room for everyone.

Show Up

One of the most important things you can do as a boss is showing up for your friends, business partners, employees, colleagues, and peers. You can’t put a price tag on having a community of support. The more you put out there for other people, the more support you’ll find in return. It’s easy to think that helping others, and even your competitors, can hurt your chances of succeeding but I challenge that. My best supporters are other bloggers and creatives who have found a niche in this industry. We share knowledge, brainstorm, and care about each other’s opinions. We celebrate each other’s successes like they’re are own. In the words of James Keller, “a candle does not lose its flame by lighting another candle.”

How to Overcome Challenges Like a Boss

Be Diligent

Let’s get real: I lived in yoga pants and took naps daily during the first month of fulltime blogging. I was frustrated with my disorganization, inefficiency, and apathy. How unworthy was I to QUIT a safe and structured job where I was steadily climbing up the ladder to start my own business if I napped and watched Netflix in PJs for a chunk of the day? Working from home can be a really cool privilege. You create your own schedule, do whatever you want, and choose all your own projects. You are your own supervisor, creative director, office manager, and CEO. Was I really choosing to be Chief Officer of Naps and make every day even more casual than “Casual Friday”?

I set rules for myself that made things simple: develop a morning routine, be at my desk by 9 a.m., get dressed in actual clothing, and take breaks to be outside and brainstorm. The workload can be volatile depending on what’s happening. You’ll realize there is ALWAYS work to be done, but setting a schedule with rules will help you be your most productive self.

Do the Math

Starting a business, blogging and freelancing are great options for creative spirits, but they come with caveats. Money can be a challenging hurdle to face in creative and freelance industries. To give you some perspective, bloggers often get paid on the net-30, net-60 or net-90 basis. That means in some cases it could take 90 days to see a paycheck from a brand partnership! There are projects I worked on in May that have yet to hit my bank account.

You’re going to want to work hard and hustle to keep the income flowing. There will be REALLY busy times but there will be slow months, too. It’s important to have a savings of three to six months of your monthly expenses before taking the leap. Some bloggers even wait until they consistently match their day job’s salary.

If you’re over the money talk, I’m not done yet! Did you know bloggers and business owners also have to set aside 30% of their income for taxes? Parting with your hard earned cash is not easy to do, so using a program like QuickBooks Self-Employed can save you time and stress. I also highly recommend reading “Worth It: Your Life, Your Money, Your Terms” by Amanda Steinberg, founder of Daily Worth.

How to Overcome Challenges Like a Boss

Stay True to Your Voice

When starting a business, it’s easy to check out what your competitors are doing. It’s okay to get inspired by others, but it’s not okay to rip off their concept or become a direct replication. I noticed myself drifting when I started to take on collaborations with brands that didn’t fit my style and values. It’s important to be stringent in your authenticity, or you WILL lose the audience who loves the real you.

You are starting your business to bring your ideas, voice, and style to life. Your ideas have value. No one has a story exactly like yours. No one says things exactly like you. Own your voice and don’t stray away from the person you are.  

Be a Fearless Trailblazer

I’ve been doing a lot of research about women in business and while we’re doing better, we still face discrimination in our industries. No matter what type of field you work in or business you own, you have to recognize how many hurdles you’ve already climbed due to your diligence as a woman. Did you know CN Traveler reported that only six percent of pilots are women?! Aviation is just one of many male-dominated industries. Women need to empower one another to be fearless trailblazers in their own path. I was personally touched by the story of Tristan, a female pilot who was empowered by Olay to share her story of overcoming adversity. I am proud to stand with her and all of the other fearless females making their mark in the world. And I’m proud to stand with you, too. Are you ready to set an example for other women to follow in your path?

Thank you to Olay for giving me the opportunity to share my story and be a fearless female ready to take on the world by helping others. What makes you fearless? I’d love to hear your stories of overcoming hurdles to get the life you want.

Stay beautiful!

XO Jillian

How to Overcome Challenges Like a Boss





This is a sponsored conversation written by me on behalf of Olay. The opinions and text are all mine.


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