5 Things No One Tells You About Being An Entrepreneur

I was 20 years old when I started my first business. Now with 20 more years of entrepreneurship under my belt, here are a few things I wish I’d known when I was starting out:


  1. Don’t Get Too Attached to Your Dreams:

I know it sounds crazy not to get too attached to a dream. But I now recognize that a dream is merely a marker for your journey ahead. A dream can be a beautiful vision for a goal. But it’s not always a goal you will hit. And that’s OK. Think of dreams as internal instigators to get you moving but also be open to having your dream ebb and flow and become more fluid. Small business owners know that you need to pair dedication, flexibility, and hard work with a dream.


  1. Relationships Are the Currency To Care Most About:

You won’t be able to build your business alone. So learn to ask for help. Find mentors. Utilize your network. You may be incredibly talented and smart and driven, but you will not and cannot maximize your success without the support of others. Surround yourself with good people to bounce ideas off of, learn new skills from, and gain feedback from. You’ll realize in the end that solid love and support is priceless.


  1. Find the Difference Between Pushy and Passionate:

No one likes a pushy sales pitch. It’s a major turn off. If you’re trying to pitch yourself or a project to someone, be genuine, be conversational, and be a human. People respect subtly and humility and while they love passion, it’s done best when you are focusing on sharing it with others, not forcing it upon others. Remember, specificity and subtly in pitching and networking can be your best asset.


  1. Taking Risks Is Non-Negotiable:

You can’t grow personally or professionally by making safe choices all the time. Take smart risks. Sometimes it’ll be a bust (a risk is a risk), but risk-taking can also open doors to incredible opportunities and relationships. And taking risks also applies to saying no to things. Saying no to a round of funding because the investor isn’t the right fit, saying no to a networking meeting because you need to focus on something else – all may seem counter intuitive but sometimes you have to risk saying no to the wrong relationships to open up space for the right ones to come through.


  1. You Don’t Need a Hobby But It Helps:

I resisted this insight for a long time because I never felt I needed a hobby – I loved to work, I was passionate about my career, and I was seeing the rewards. But then ultimately (and inevitably) a burn out happens. And you realize that you’ve not spent time cultivating your most important asset – YOU! So even if it’s reading, taking walks, traveling or knitting – find something that you can do for you. Not for the business. Do it because it makes you happy, makes you wiser, makes you relax. The best entrepreneurs I know are well rounded and don’t forget to play as much as they work!


How To Enjoy Your Moment

We work so hard.


Go to school. Train. Pray. Sacrifice. Repeat.


We dream so big.


Face disappointment. Bounce back. Fall down. Repeat.


We psych ourselves up.


Pep talk. Cry. Mope. Pep Talk. Repeat.


We make vision boards.


We chant mantras.


We tell our secrets to friends in hopes they come true.


We wish ourselves to sleep every night with what we desire.


We daydream and fantasize about the moment.


Then it happens.


The new job.


The love of your life.


The healthier body.


The promotion.


The green light.


The go-ahead.


The moment you’ve been waiting for.


And you stress.


Worry, Feel Anxious, Doubt. Repeat.


Question your deservedness.


Beg for a bit more time.


Swear you are unprepared.


Sabotage. Suffer. Shrink. Repeat.


But what if you enjoyed your moment.


Soaked it in.


Breathed it out.


Wallowed in the goodness happening now.


Believed you were worth it.


Smiled at the thought of it.


The taste of it.


The feel of it.


Reminded yourself you are allowed to feel good.


And then actually felt good.


Without guilt. Remorse. Or Shame.


You can enjoy your moment.


All you need to do is – feel grateful.




S.F.S.N. = Sounds Fabulous, Signifies Nothing

“You go girl!” “Just Be Confident!” “Be your true self!”


We are bombarded with messages like these everyday. Top 10 lists on loving our body. Quizzes about what superhero we’d be.


Messages like these sound good. They seem like the right thing to tell ourselves, our friends, our kids, our families. But do they actually DO anything?


They are what I call, “S.F.S.N. – sounds fabulous, signifies nothing.”


These quotes and phrases are meant to inspire us and shake us out of a rut. So why then can they sometimes feel hollow? Because they tend to ignore the most important part of the journey to confidence- the HOW we get there.


And that’s because there isn’t a universal HOW. Everyone’s process will vary. In approach, style and technique. Some have to hit bottom before bouncing back. Others need to get knocked down only once. Some of us will spend decades searching. Some of us will spend days.


The path to self-confidence is sometimes less about the rah-rah and more about the raw. The real. The messy. (and there’s often not a cute quote card for that!)


Why I Love “Reverse Mentoring”

Some people have hobbies like baking or building those little ships in bottles (do people still do that?)


I’d say my main hobby is mentoring.


Yep. I collect mentees like some people collected Tiger Beat posters of Rob Lowe back in the day. (Anyone? No? Just me?)


Many people might think of a mentor/mentee relationship as a one-way street, but if you are lucky, you get what I call “reverse mentoring.” The collective wisdom, insight, and inspiration you receive by helping someone on their journey.


I get such an incredible gift from having mentees in my life.


Here are 6 women I’ve mentored and what they’ve taught me in return.




Emily-Anne Rigal, We Stop Hate


I’ve known Emily-Anne since she was 15! She has now created a media empire through her anti-bullying organization We Stop Hate and her new book, Flawd. I’m inspired by her commitment to creating a community that inspires individual change.


She’s also taught me the joys of selfie-taking, social media and when to use the right emoticons. 🙂




Cammy Nelson, Brave Like Me


I met Cammy when she was in 6th grade and knew she was destined to be a force in the confidence community. She works with girls across the country to redefine bravery as taking risks and taking action – no matter how big or small.


Cammy has taught me about the tenderness of forgiving oneself and the glory of speaking about your dreams while in swimming pools.




Kara Norman, Empower Her, Inc.


Kara thinks I’m mentoring her, but truly she has helped me through her devout faith, passion, and generous heart. She provides events, resources, and programs that help women and girls live fulfilled lives in her community of Atlanta, Georgia. Even when faced with difficult challenges, she rises to the occasion and models grace in action.




Megan Grassell, Yellowberry


So truth is, I cold-called Megan and her Mom after I read about Yellowberry and I’m pretty sure they both thought I was a crazy creepster offering my help and mentorship. But I truly knew that Megan was on to something HUGE. Her ambition and drive led her to create a business that helps young girls feel confident about wearing a bra for the first time. I’m grateful that Megan ended up trusting me and didn’t hang up the phone!




Molly Thompson & Lauren Paul, Kind Campaign


My world got better when these two filmmakers and activists stepped into it. After appearing in their groundbreaking documentary on bullying, “Finding Kind”, we ended up mentoring each other over the years. They are so wholly dedicated to spreading kindness and positivity to women and girls worldwide. I’ll forever be indebted to them for the kindness they showed me on the floor of a movie theatre in Somewhere, USA – crying over broken hearts and big life changes.




Tammy Tibbetts, She’s The First


I first met Tammy during my Seventeen magazine days, and now she’s the Founder and President of an amazing organization that provides scholarships to educate girls in developing countries. Watching her grow professionally over the years inspires me to remember that growth and success take time – but are ultimately worth the wait.


Confidence Is Fashionable

What a fabulous day!


I never thought I’d find myself strutting my stuff down a runway at New York Fashion Week – yet, here we are!


Today I walked in designer Carrie Hammer’s “Role Models, Not Runway Models” fashion show! The vision of this show is to create a “runway revolution” by featuring a variety of bad ass professional women – from all different backgrounds, sizes, shapes, abilities and nationalities.




Woke up bright and early—bare faced and full-hearted—feeling excited and inspired and overjoyed. Watch my morning pep talk here!




First stop: Hair and make-up! That’s Tiffany and she did an excellent job glamming me up.


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Luckily, I had the opportunity to rehearse my fierce walk before the real thing and totally didn’t fall! (Which was my biggest fear)


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Showtime!! (At this point I’m thinking “Is this really happening?” and “Please don’t let me fall!”)


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AND BAM! There I am!! Today I wasn’t just talking about confidence; I was literally walking the talk in what one lovely Tweeter described as “Jess Weiner serving up some sass!” Yes, indeed.


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I was also joined by some incredible role models including CEOs, entrepreneurs, editors, and more – all celebrating inner and outer diversity and confidence. (Left to right: Michelle Herrera of Cosmo Latina, Melissa Miranda of PepsiCo, and Tolu Olubunmi of DREAM Act)


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After the show: Camera flashes! Press photos! Meet-n-greets! Just like that, my fabulous runway adventure had come to an end. Of course, a celebration wouldn’t be complete without my sweet husband there to root me on and the influx of love and support I received in person and on social media.


I love mentoring and role modeling because it also leaves me feeling inspired and supported and reminded that we’re not alone as we travel through this life.


So wherever you are in life – let’s all just take our place on the runway and WORK IT!!





Most days when I sit down to write these posts, I have no idea where to start.


I think about writing something witty, snarky, silly.


I think about using the time to uplift, inspire, educate.


I feel pressure to speak about my work, the business, stuff that makes money.
But if I’m silent enough. And still enough. What comes to me is this…


Sometimes I don’t want to write anything. I want to be in gestation, growing new ideas and thoughts. I don’t always want to produce for production sake, and I don’t want to worry about whether or not it gets a response.


In the silence, I can hear a smaller voice emerge, one that says to take a step back not forward. To sit not pace. To listen not talk. And if I do listen, I can hear the tiny sounds of new ideas rushing to be formed and my patience rising up like a swell.


I sit and I listen.


And I always end up writing.


But it’s never what I thought it would be.


5 Things I Wish I Knew About Confidence

  1. It’s Messy: True confidence can look like you lived through a food fight with your emotions. You often have to travel down some rocky roads and building confidence never seems to look like those lovely movie montages where everything’s resolved at the end of a great song. Cultivating confidence in your life won’t look pretty all the time, so don’t try and hide the mess.

  3. There is no time limit: I almost hesitated making this list because confidence can’t be achieved in 5, 10 or 20 easy steps. It’s an accumulation of your inner work and the risks you take in life to build your character. Self-discovery is a life long journey. So stop stressing if you aren’t where you want to be confidence-wise in your teens, 20’s or 50’s. It’s something we’ll probably never figure out really, so we might as well enjoy the ride.

  5. It’s not permanent: It’s tempting to think that once you ‘have’ confidence you can maintain it for the rest of your life. But much like a gas tank for your car, the feeling of confidence must be replenished and filled up over time. It’s normal for even the most confident people to go through bouts of feeling down, defeated and broken. What’s important is not to give up on creating those moments in life where you are learning and growing, because it’s those experiences that actually build your confidence.

  7. You will HAVE to feel pain: Sorry, but there’s no way around it. Feeling pain is an important part of growing confident. Because it’s when you get to the other side of pain, heartbreak, embarrassment, and fear that you figure out what it means to feel pride, strength, and resilience. And these are the building blocks of truly confident people.

  9. It’s Ultimately Worth It: Learning to love your own company, discovering who you are in the face of adversity, achieving something you never thought possible, believing that you are worth feeling strong and supported — these are all the benefits of building confidence. It’s a marathon, baby, not a sprint. And we just started running.