Top 3 Biggest Lessons For An Entrepreneur

I’m close to the 5th anniversary of starting my own business and that’s a huge milestone for me. I’ve been thinking a lot about how far I have come… about my successes and the good times AND all the mistakes I’m grateful I made because they’ve made me and my business better.

Here are my three biggest lessons (because that’s all mistakes really are, IF you’re paying attention):

1. Not asking for help. Part of this was just being cheap. I made excuses then about not being able to afford help, but that revealed the deeper issue — FEAR. I was afraid to admit I couldn’t do it on my own (which I falsely believed was at the core of owning my own business) and I was afraid I wouldn’t make enough to pay my own personal bills, much less anybody else. So I tried to do everything on my own – even my quarterly tax reports! In no known universe should I have EVER been doing any kind of bookkeeping to that level. All that did was steal far too much time and energy away from what I should have been focused on. My time and my energy are essential to my business thriving… but I was constricting that with all the heavy lifting and frustration of the day-to-day. Now, I consider finding and engaging help as a mission-critical investment. Currently, I have 5-7 people supporting me at any given time and I could easily grow that number (and probably will) in the near future.

2. Not charging enough for my services and expertise. And to be honest, I still struggle with this one as my business and I grow. Understanding and knowing your value is at the core of what I teach my clients on all levels… because to me, it’s the core of having and creating success. If you understand what’s special about who you are, what you do and the value it brings to others, then you’ll always know what your work is worth. Your unique combination of qualities is what differentiates you from the next person, even if they provide something similar. Once you figure that out, it’s easier to set your rates or pricing for your products that makes sense for you and your marketplace. It’s a continual process as you grow and change but after you do it the first time and see the results, you’ll get better at it.

3. Not starting sooner. I’ve had ideas for businesses for YEARS… at least 10 years before I actually incorporated my current business. But I never acted on them… partly because I didn’t think I had the skills for entrepreneurship, partly because of fear that they weren’t really viable. While I believe everything happens as it should, when we’re ready and I have no regrets, I wish I had tried some of those ideas when I got them. Knowing what I know now, I could have pulled off at least one of them while I was working full-time and I would have learned the first two lessons sooner. But mostly I wonder, what they could have become?

And these are only the top three… I share them in the hopes that you avoid them and learn the lessons I already did, so you’ll have the energy for the mistakes you’ll make and learn from. To me, this is just another step on my journey living in Fearless Authenticity… it takes vulnerability, strength and tenacity to look at yourself, know and admit you screwed up, then choose to do something different. And that’s what it takes to be better at whatever you want to be — person, leader, salesperson, co-worker, business owner — and see more success as you define it.

Here’s to celebrating the imperfections along the way!

Harnessing Emotions in the Office

I was honored to be the emcee for the Chicago Walk to End Alzheimer’s at Soldier Field recently. As I reflect on that gorgeous day, I’m reminded of how blessed I am to be able to support causes that are near and dear to my heart while doing what I love, on-stage or on-camera.
I had a really emotional moment on stage that day and it got me thinking about emotions in the workplace and how my approach to it has changed over time. The loss of my father is still very raw and present in my heart and mind and I started crying during the Promise Garden ceremony… a tender moment of the program where we honor the reason why we walk. It was TOUGH.

I have spent 30-some years talking to and performing in front of people. I give robust and personal keynote speeches on a regular basis and I think it’s fair to say that there’s an expectation to always hold it together in public (and especially on stage), no matter how challenging it might be. At least that’s the expectation that I have had for myself for quite some time.

People at the walk were super supportive. I looked out into the crowd and saw so many people smiling knowingly, sending love and crying along with me that it felt good to share my experience. Their empathy and kindness was soothing, cleansing and even empowering. That’s when I realized again for myself the thing that I remind my clients of oftern — that emotion fuels response in all of us.

I think we, as women in particular, may overcompensate in the other direction, thinking that emotions have no place at work. Clearly, some emotions are inappropriate, disruptive and unproductive, but if you think about the people who really are the best leaders, they lead with passion. Passion is an emotion and there’s nothing derogatory about that word. A great leader will express their joy or displeasure about something and that’s what motivates action and gets a response. And I think it’s time that we ALL do that more.

I talk about authenticity with my clients and with my audiences all the time. And I will continue to shout this from the rooftop: there is SO much value in bringing our whole selves as well as our experiences to our work.

Of course, there will inevitably be times when you should say, “I need a moment.” That’s healthy and there’s nothing to be ashamed of in taking a break to regroup. There will also be some people or groups you’re just not going to be vulnerable with for any number of good reasons. That’s absolutely fine. Check your fear, but trust your gut. When you do, you’ll know the right situations where it could really move things forward for you.
I know that for me, there have been many times where I have held things in for far too long… it’s so draining and has never really been worth it. In the past few years, I have had colleagues and work friends say that they’re glad to see more of me and that they love how I’m sharing more facets of who I am. That’s affirming. I’m not looking for validation but those moments confirm to me that I’m adding more value to someone else’s experience by doing so. Vulnerability and empathy build trust and foster stronger relationships.

So, going forward, here’s my message to you.

Do not be afraid to show your emotions (reasonably and only when you’re comfortable) because it will help build connections you didn’t know were possible. Our success is in who we are. Not just what we do. It’s also in the way that we do what we do… emotions are an essential part of that and your future successes. And that’s all authentic and truly fearless!

How to Simplify Everything

In my efforts to live more authentically, I have tried to slow my life down and bring more order to my crowded schedule but of course, it’s a challenge every single day! In addition to my 30+ years of work in radio and television, I’m a public speaker, panel moderator, virtual events host, and business coach (not to mention, daughter, aunt, friend, and colleague). And obviously, I am not alone. Every day, I talk with at least one person who can’t find enough time to check even a few items off their long to-do list. They are CEOs, middle managers, organization leaders, and small business owners who are overwhelmed and sometimes paralyzed to make decisions. When you have 1000 things on your mind at work (along with personal stuff like family, friends, exercise, staying healthy, etc.), it’s incredibly hard to even think much less make a tough decision. So how do you fight through the all the noise and bring a semblance of order to your day? The first thing I do is ACTIVELY SIMPLIFY EVERYTHING.  Here’s how:
  1. Acknowledge what you want. Acknowledge what you need. Acknowledge how you feel. Sit down in a quiet place, set a timer, and think just about these things. Write them down. The “feel” may be challenging because it may conflict with what you want or need. 
  2. Choose what supports those things. Is it saying no? Is it asking for help? If there is a conflict between those three (what you want, need, and feel), learn to prioritize and then make your choice.
  3. Be honest. This is an exercise that you’re doing with yourself. There is no point in trying to convince yourself of feeling one way or another. There’s no judgment here. And that includes guilt. Sometimes when you actively think about how you feel or what you want, guilt bubbles up, because your choice may not lend itself to what you actually need.
  4. Commit to letting things go. After you commit to it, celebrate it! Remind yourself of what you’ve been able to do by letting go.
  5. Ask for it. Whether it’s hiring actual help or just asking a friend for support. Maybe you need a colleague to help you stay accountable to your goal. All you need to do is ask.
  6. There certainly is no definitive cure for feeling overwhelmed or frustrated; it’s different for everyone. But organizing your thoughts can be the place to start. I guarantee the process will help you learn to know your true self and reveal your authenticity … leading to a more productive and peaceful life.
Do you have a secret to simplifying your life? Please share!