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Annie M. Henderson: “Sense of humor”

Sense of humor. Laughter has always been the best medicine. Learning to laugh at oneself when mistakes occur, will always be better than beating yourself up like we so often do. Various studies have shown that laughter has positive psychological effects, as well as boosting the immune system. Internal Validation. Sure it feels great to have […]

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Sense of humor. Laughter has always been the best medicine. Learning to laugh at oneself when mistakes occur, will always be better than beating yourself up like we so often do. Various studies have shown that laughter has positive psychological effects, as well as boosting the immune system.

Internal Validation. Sure it feels great to have that extra boost when someone validates you and tells you, “Way to go! I’m so proud of all the hard work!” but unfortunately, entrepreneurs have so many unseen wins and moments of growth, that we often have to be our own cheerleaders. This is when internal validation is so valuable. Making internal validation a part of your daily routine through affirmations, self-care, and acknowledging your own strengths, successes, progress and effort, can go a long way, especially when support might not be readily available.


Being a founder, entrepreneur, or business owner can have many exciting and thrilling moments. But it is also punctuated with periods of doubt, slump, and anxiety. So how does one successfully and healthily ride the highs and lows of Entrepreneurship? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Annie Henderson.

Annie M Henderson is a Certified Professional Life Coach specializing as a Coming Out Coach for the LGBTQIA community and helps people-pleasers that avoid conflict, over apologize, and struggle to say no, start living authentically and find the peace they have been missing.

After going from an unfulfilled existence checking all the boxes of perceived “success,” to breaking into an intentional, abundant life, she now uses her experiences and professional background as a teacher, counselor, and life coach, to teach and mentor others. In working with her diverse clientele to discover unapologetic joy, including the LGBTQIA community and people-pleasers, her teachings focus on releasing self-doubt, embracing the power in setting boundaries and removing the habit of staying in our comfort zones.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

I was always destined to help others and have always loved psychology. My bachelor’s degree was in psychology and before jumping into being a teacher, I got my Master’s of Elementary Education. It was a blast to teach, support, and mold young minds and I eventually combined my two loves as I got my Master’s of School Counseling and my Master’s of Professional Counseling. I spent a little over 15 years in education and finally left to help people and explore entrepreneurship. With a lot of patience from my partner and excitement from my child, I couldn’t be happier with this decision even with all the highs and lows along the way!

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

My AHA moment for becoming a Coming Out Coach was when my podcast co-host interviewed me about my own coming out journey. At the time I was focused on helping overwhelmed moms and after this episode aired, I had several people reach out to me to share their stories and one became a client whose daughter had come out. That’s when I realized I could help so many people that needed someone that understood what they were going though but didn’t feel like they could share with friends, family, church or even on social media.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

I’ll have to say it is in my blood! My father has always been an entrepreneur so while I’ve always had the itch, I definitely had my own share of growing pains and lessons to learn along the way. One thing I had to learn is that although I can try and do everything, it’s not always the best business decision. I had to start asking myself, where is my zone of genius and how can I best use my talents and time? What are areas I can delegate or hire someone else?

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

My cousin once told me, “Your dad has the Midas touch!” Anything he tried, he could make money. This was always inspiring to me to see how he might be buying/selling something that everyone has their doubts on, and he could care less. That self-confidence and courage to go out and try something new has stuck with me.

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

I often hear comments like, “I’ve never heard of a Coming Out Coach” or “I could have used someone like you when I was younger” and it reminds me that I’m doing the right thing. In a time where the industry of life coaching is constantly growing, I’m grateful that I can stand out and help in a way that saves lives and relationships.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

1.Patience to grow a life coaching practice from scratch is instrumental. The first year, I was blessed to have clients, but in no way did it replace my old income as a school counselor and LPC. I had to be patient and believe in myself and what I wanted to do, even if it was unconventional.

2.Courage is the word one of my coworkers painted on a stone as my going away gift. One must have courage when stepping out into the unknown to try something new that they have no guarantee will work. I’m so thankful to have this courage, not only to become a life coach but to live authentically and to reach out to those that may be too scared to ask for help.

3.Confidence in knowing that I can help the people that reach out to me, is something that can make or break a coach or counselor. Early on, I questioned myself and I was unsure if I was the right person to be helping anyone! Just like anything, confidence grows with each success, each testimonial, and now when someone hops on a consultation call, I have confidence in my ability to help them and it comes across in my energy.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

What a great twist! Let’s tackle this advice: “Go to college and get a good job.” Spoiler alert: I did both of these things and I currently am not in the same job or using any of the 4 degrees that I worked so hard for. What is great advice for one is not always perfect advice for others. I see so many people get into jobs and feel trapped because they are making a certain amount of money and the thought of starting over is paralyzing. They end up trapped and miserable because they were doing what they thought was right.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

Self-care is not selfish! Your employees, your clients, and your family will benefit the most when you take care of you first. This could look like exercise, a vacation, a daily walk, brunch with friends, turning work off at a certain time so that you can have quality time doing something that fills you up. By doing this, you have a better chance at preventing overwhelm and burnout.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

Be consistent! Show up and be your audience’s go-to source for what it is you provide. Online it can be the post that starts their day off on a positive spin. We can create credibility, trust and authority by adding some consistency to their lives that is helpful instead of anxiety producing like the news, family, or coworkers.!

Can you help articulate why doing that is essential today?

In a world where people are getting better about curating their online experience, you want to be someone that stands out in a good way. Instead of being a part of the noise, blocked, or unsubscribed, ask yourself what you have to offer and what would keep you coming back for more if the shoe was on the other foot.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

“I wouldn’t want to build a castle that I don’t want to live in.” I heard this quote and it stuck with me. A common mistake that CEOs and founders are making is creating something that isn’t sustainable or enjoyable. Having the thought instead be, “How can I make this the best experience for everyone?” can shift the outcome and help avoid these kinds of errors.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

As an entrepreneur, the highs and lows that come will obviously be different than a “regular job.” I remember back in my 9–5 job when the money consistently showed up, no matter what kind of day I had or how productive I felt. I didn’t have to market for myself and I didn’t pay for my office. As an entrepreneur you are creating a lot of your own rules and your pay is not always consistent, depending on your business model. Being mentally, emotionally, and financially prepared is crucial to be able to navigate all the highs and lows.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

A time I was feeling unusually excited was during 2020 after my best month as a life coach. TikTok is an amazing platform to be able to connect with your audience on a more personal level! I never thought I would be getting most of my clients from what most assumed is social media for dancing kids. HA!

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

As I mentioned before, life coaching for me was a sloooow start. It was a struggle and there were times that I considered going back to a 9–5 job because it was getting scary financially. Having those regular money talks with my financial advisor/partner felt soul-crushing because the numbers were not going the way we hoped. This was an unusually low and vulnerable time in my business.

Based on your experience can you tell us what you did to bounce back?

To bounce back from those super-low moments, I focused on my WHY. I focused on helping others and changing lives. I worked on being consistent and not giving up even though all evidence pointed to GET OUT NOW!

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

  1. Support Group. Without a support group, I may have given up way before I reached success! I often tell my clients about crabs in a bucket and how when one crab starts to crawl out, the others will pull them back down. Sadly, this can be like our friends and family that don’t fully grasp why we want to do anything different than the status quo. Connecting with a group of people, an accountability buddy, or a coach can make the difference between escaping the bucket and being dragged back down.

2. Growth Mindset. To survive the emotional lows of being an entrepreneur, I believe having a growth mindset is a must! Carol Dweck said,”In a growth mindset, challenges are exciting rather than threatening.” Those with a fixed mindset tend to give up faster, beat themselves up, and feel they have fixed abilities. To survive the ups and downs, a growth mindset must be fostered.

3. Sense of humor. Laughter has always been the best medicine. Learning to laugh at oneself when mistakes occur, will always be better than beating yourself up like we so often do. Various studies have shown that laughter has positive psychological effects, as well as boosting the immune system.

4. Your WHY. Simon Sinek, author of Find Your Why, says, “Working hard for something we don’t care about is called stress. Working hard for something we love is called passion.” Without your true reason for doing what you do, something beyond just money, this journey called entrepreneurship will have more uphill battles than needed. Each day you start over and to have your WHY give you vision, passion, and motivation as opposed to “have to”, “need to”, and “supposed to.” They just hit differently, right?

5. Internal Validation. Sure it feels great to have that extra boost when someone validates you and tells you, “Way to go! I’m so proud of all the hard work!” but unfortunately, entrepreneurs have so many unseen wins and moments of growth, that we often have to be our own cheerleaders. This is when internal validation is so valuable. Making internal validation a part of your daily routine through affirmations, self-care, and acknowledging your own strengths, successes, progress and effort, can go a long way, especially when support might not be readily available.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

Resilience is the ability to recover quickly from tough situations. Some of the traits of resilient people include being a good communicator, being a problem solver, someone that reaches for curiosity instead of anger or blame. I truly believe these characteristics not only make an amazing entrepreneur but also a healthy human being.

Did you have any experiences growing up that have contributed to building your resiliency? Would you mind sharing a story?

Coming from a family that included some mental illness, a life-threatening car accident, and divorce when I was in high school, all helped shape who I am and how I began handling things in life. These major events definitely helped build resiliency and I had to choose at that crucial time in my life if I wanted to become a victim and blame my circumstances or start making my own choices, attitude, and results.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

Calmness and positivity is something that others have noticed in how I handle difficult situations. Something that has helped me do this all along the journey has been the realization that the only things that I am in control of are my own thoughts, feelings, and actions. A shirt I got for my daughter states, “Not my circus, not my monkeys.” My goal is to instill this positive attitude and to remind her that she is not responsible for others’ reactions.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

I’ve heard many times that if you are about to hop on a phone call, you should be smiling before you even start to dial. Such an excellent reminder that our attitude, energy, and thoughts make it to our clients and team even without intentionally doing so. So often, leaders think they can hide it when something devastating is going on in their life, but it usually bleeds into the company. As a life coach, I am extra aware of how my attitude influences those I touch via social media due to the messages and comments I receive. Recently, a follower on Facebook messaged me letting me know how much it means to them to start off their day with this dose of positivity. These messages mean the world and are such a helpful reminder that my positivity is making an impact.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

“People often say that motivation doesn’t last. Well, neither does bathing — that’s why we recommend it daily.”

Zig Ziglar

This quote is something that sticks with me. Many times, people will try something once and be disappointed when it doesn’t work out. As Zig Ziglar points out, it’s like bathing. We need to stick with motivation, stick with pursuing greatness, stick to our WHY!

Don’t give up on our dreams because we don’t get the results we want as quick as we want them.

How can our readers further follow you online?

Come visit me at www.anniemhenderson.com to listen to my podcast, connect on Facebook, TikTok, or sign up for coaching.

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

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