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“Find a Board of Mentors” 5 Leadership Lessons with Alissa Carpenter

“Find a board of mentors. I always advocate to my clients and former students to find a group of people you know, like and trust. This is essential when running your business as well. Surrounding yourself with people who are willing to invest time in you and the success of your business is crucial! My mentors are my biggest advocates and cheerleaders and are the first people to challenge and push me. They are not afraid to tell me if I am doing something wrong and how I might be able to improve the process. Their honesty drives me to move forward and has helped me to successfully grow my business.”
I had the pleasure of interviewing Alissa Carpenter, founder and principal consultant of Everything’s Not OK and That’s OK, a coaching leadership, and consulting company focused on bridging generational silos in the workplace. Alissa is a Gallup-Certified Strengths Coach and has been featured on NPR, ABC7, CBS6, PHL17, contributor for Forbes and quoted in multiple media outlets including CNN Money and Moneyish.

Thank you so much for doing this with us! What is your “backstory”?

My professional background is as a Higher Education Administrator where I advised Millennial and Gen Z students at top-tier institutions, including the Wharton School and Pennsylvania State University. I would see students smiling, laughing and telling their friends how great they did on a last test, how many job offers they received or how awesome their weekend was. The same students would then come to my office and break down about a recent failure or how they bombed that very same test they boasted about to their friends.

Time and time again, students would put on a face for their peers to have them believe that everything was OK, when they were really struggling. The only time they would mention anything to a peer would be after they overcame it. I wanted to find a way to bring more awareness to the fact that everything is not always OK, and that’s OK. We all fail and it’s important to let others in so they can help and support you. More than likely your friend is probably going through the same thing, but too afraid to say anything.

I decided to earn several certifications, including Gallup’s StrengthsFinder, to find the language to help people, regardless of how hopeless they were feeling to find the positive and to leverage their strengths to find a way out of their situation.

In 2015, I decided to start my business, Everything’s Not OK and That’s OK, where I focused on career coaching millennials and individuals looking to make a career pivot. After some soul-searching and many long conversations with my husband, I decided to leave Wharton in 2017 and pursue my business full time. I wanted to have a bigger impact and help more people bridge silos, identify their strengths, and make plans to move forward.

After I took the business full time, I branched out to administer strengths-based leadership trainings to companies and organizations as I could make a bigger impact, faster. I knew I wanted to be more on the front line and be the bridge between generations, help all employees find their super power, and create a space to have open lines of communication.

My customizable trainings help new supervisors reach their untapped potential by providing tools and identifying their strengths to navigate their new role successfully. I also coach and train employees on all levels on bridging generational silos and create strengths-based teams to increase engagement, productivity, and profitability.

Looking back at the past year, it seems like a whirlwind. I’ve worked with a variety of companies, from non-profits to multi-billion-dollar enterprises, became a Forbes contributor, have been quoted as an expert in several publications, and go on media appearances. I am truly honored and humbled to be where I am now and hoping I can continue to spread the message, “everything’s not OK and that’s OK.”

Can you share the funniest or most interesting story that happened to you since you started your company

I host trainings and give speeches on a variety of topics, including Millennials in the workforce. After spending many years working with Millennials and Gen Z, I knew there was not only a disconnect from what was taught in college and applied in the workplace, but also a need to bridge generational silos in the workforce. What I didn’t realize was the extreme desire to not be associated with the Millennial generation and the unfairly negative stereotypes associated with it. I knew they were there, but didn’t realize how badly they needed to be broken down.

When I first started I was overwhelmed with hearing things like, “I don’t want to be associated with this generation, I’m not lazy or entitled” “Why are Millennials the worst?” “Is there any way my company can avoid hiring Millennials?” This negativity was coming from both Millennials and non-Millennials. I often had people try to argue they shouldn’t be considered millennials despite clearly falling within the age range.

Instead of letting it frustrate me, I let it empower me to provide a safe space to have conversations not only about our differences, but our similarities. Once you break down the layers, and open the lines of communication to outline the common goals and visions, the rewards speak for themselves and I am humbled to be a part of that process for so many people.

What do you think makes your company stand out? Can you share a story?

“Everything is Not OK and That’s OK” is not just a business name to me. I work hard to be transparent and let my audience know when I’m struggling. I’m no different than anyone else; I’m not super human. I am just passionate about practicing what I preach. I work hard work through failures and make it work as a business owner with two little kids. It’s important to me that we share our struggles as we are going through them, not just when we’ve overcome them. Open up, be vulnerable, and be human!

When I first started my business and blog, I wanted to get stories from other people who were not afraid to share what they were going through. Each week I featured brilliant and beautiful stories from people who didn’t get into their top choice school, were struggling to find jobs, suffer from depression, or had a child and debating what their next step should be. These stories inspired conversations with others and led me to want to start a podcast, Millennial Playbook Podcast, to get more “real life” stories and for others to learn from our similar and shared experiences. I continue to admire these stories as it’s not easy to put yourself out there, but when we do it’s so powerful and can impact so many other people going through the same thing.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story

My husband is my true rock. When I said I wanted to leave my steady position at the Wharton School, he never questioned my ability to create a successful business. He recognized my drive and determination, or my desire to try something I’ve never done before-be an entrepreneur. He is in the financial industry and suggested taking a business planning course to get started on the right foot. We worked together through the numbers to make sure I was setting myself and our family up for success. I really don’t know what I would do without him!

How have you used your success to bring goodness to the world?

No matter what is going on in life, I want people to know they are worthy and capable of making a change. It takes us several steps to get to a “bad” place and will take us several to get out of it, but I want to continue to spread the positive message that it’s possible to make it through.

What are your “5 things I wish someone told me before I launched my Start-Up” and why. Please share a story or example for each.

  1. Owning and running a business is an emotional rollercoaster. One day I can feel like I’m on top of the world and the next day like I’ve taken five steps backwards. I knew that running a business would take a toll on my emotions, but didn’t realize how much they would ebb and flow through the process. One day a business will sign and contract and the next someone will go with another vendor without a reason. It’s important to take time for yourself and celebrate every small win that comes your way because those small victories will be what helps you move forward and past your “backwards” moments.
  2. Running a company is expensive. As a service industry, I knew my business would have some overhead, but I didn’t realize how much. I took a strategic business planning course to see what a years’ expenses would cost and it added up quickly. Small things like PO Boxes, graphic design fees, marketing materials, and website development will take a large chunk out of your income. Take the time to really assess your expenses and establish the income you need to make a profit before you even start your business.
  3. Pay yourself! When you’re running a business, it’s so important to pay yourself. I sat down with a mentor to figure out how much money I can and should be taking out of my earnings each month and how much I should be reinvesting in the business.
  4. Find a board of mentors. I always advocate to my clients and former students to find a group of people you know, like and trust. This is essential when running your business as well. Surrounding yourself with people who are willing to invest time in you and the success of your business is crucial! My mentors are my biggest advocates and cheerleaders and are the first people to challenge and push me. They are not afraid to tell me if I am doing something wrong and how I might be able to improve the process. Their honesty drives me to move forward and has helped me to successfully grow my business.
  5. Plan your days off. When you work from home, your business can easily take over your life. As soon as I left my full-time job, I found myself working easily 14–18-hour days during the week and unexpected time on the weekends. I wasn’t giving myself a break other than to get something to eat, pick up my kids from school and to sleep. I knew this wasn’t sustainable and started planning and scheduling days off and adding them to my calendar. I also now make it a point to go to bed at a reasonable time, pre-plan healthy meals, and workout four times a week.

Some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US whom you would love to have a private breakfast or lunch with, and why? He or she might see this. :-)

This is one of my favorite questions and I would love to have a mimosa breakfast with Mindy Kaling. Among her being relatable, funny and charismatic, the waves she has made in the entertainment industry are astounding. She didn’t give up on her dreams, worked incredibly hard to get there, and is a true inspiration to all women. I had the opportunity to hear her speak at the PA Conference for Women and I couldn’t stop smiling during the entire 30-minute Q and A. I know I could learn a lot from her perseverance, determination, and talent all while having a great belly laugh. Plus, breakfast is my favorite meal of the day.