Get some friends who are doing what you want to do. It isn’t easy to believe you can do something if you’ve never known anyone who’s done it before. For example, my friend Jenny opened me up to a world of recurring income. Before I met her, I never knew this world existed outside of Multi-Level marketing companies, which I was not interested in.

Starting something new is scary. Learning to believe in yourself can be a critical precursor to starting a new initiative. Why is it so important to learn to believe in yourself? How can someone work on gaining these skills? In this interview series, we are talking to business leaders, authors, writers, coaches, medical professionals, teachers, to share empowering insights about “How To Learn To Believe In Yourself.” As a part of this series we had the pleasure of interviewing Kathe Kline.

Kathe had 30 years of Financial Planning experience and worked with over 2,000 clients before she retired as a Financial Advisor in 2020.

She started working with Medicare in 2014 when she found out her husband would have a lifetime penalty because the insurance agent he used to sign up for a Medicare Supplement Plan didn’t explain his options adequately. Her goal is to help others easily navigate Medicare so they can make the right decisions.

Before moving to South Carolina, Kathe volunteered for North County Health Services, which had ten community clinics throughout northern San Diego County. She has also been a Big Sister volunteer, and she helped SCORE San Diego set up their mastermind group programs for business owners.

She spends her time doing art projects, playing with her husband and her dog Izzy, and helping other insurance agents connect with consumers through her website,

Thank you so much for joining us in this interview series! Before we dive into the main focus of our interview, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

After my mom and dad divorced, my mother struggled with finances. I remember we were on food stamps for most of my childhood. We didn’t live near my father, and my parents had split up the four children — two lived with my mother, and two lived with my father.

As a result, I didn’t get to grow up with my older sister and my younger brother.

My younger sister and I stayed with my mother, who gave us food stamps as our allowance. I was always better with money than my mother was, and I remember as a young girl, my mother often borrowed money from me (she always paid it back).

What or who inspired you to pursue your career? We’d love to hear the story.

I had a friend named Jenny who had inherited an insurance business from her father. She told me how you could sell a medical policy one time and get paid every year as long as the person remained your client. Her story intrigued me and led to my job in Financial Services.

Although there are different types of careers in this field, I stuck with services where I got paid as my client’s balances grew.

It has been said that our mistakes can be our greatest teachers. Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I don’t have a story about Financial Planning, but I do have one regarding Medicare. I couldn’t understand why I wasn’t “getting” it. It came down to the terminology. I was confusing PLAN A with PART A, Plan B with PART B, and Plan C with Part C.

It’s funny that our officials would name things in that manner that is bound to confuse people!

What are some of the most interesting or exciting projects you are working on now? How do you think that might help people?

I realized that consumers all over the country, not just near me, need help with Medicare. And I also recognize that not all insurance agents are qualified to help people with that plan. That’s because when my husband turned 65, we had an insurance agent set up his Medicare Supplement Plan for him. This agent put himself out there as a Medicare expert, but he wasn’t.

We know that now because when he was done signing my husband up for his supplement plan, he asked if my husband was taking any medications. Since he didn’t, the insurance guy told him he didn’t need a drug plan.

We found out that there was a penalty five years later. So we signed him up as soon as we could. The problem is that now my husband has to pay a penalty that will last as long as he lives.

That insurance guy never mentioned this penalty. Our penalty is more than the drug plan costs.

OK, thank you for all of that. Let’s now shift to the core focus of our interview.

This will be intuitive to you but it will be helpful to spell this out directly. Can you help explain a few reasons why it is so important to believe in yourself? Can you share a story or give some examples?

When I was younger, I didn’t believe in myself.

I didn’t know what I was going to do or be. I didn’t go to college right out of high school because I didn’t know how to complete the paperwork. Although I did well in school, I didn’t try very hard because I didn’t realize how important getting into a college would be for my future. My main goal was to get a job at a clothing store. And I didn’t believe I was good enough for that job since I didn’t dress the same way the clothing store employees dressed.

If you don’t believe that you can do something, you won’t even try. For example, did you know they train elephants? Have you ever heard of a flea circus? In both cases, they train the animals NOT to believe they can do something. In the case of elephants, they get them when they are little and tie one of their front legs to a stake in the ground. They struggle to get out of it, but because they are tiny, they can’t. They then stop trying, even after growing very large, and could easily break the rope tying them to the stake. They don’t believe in themselves and so cannot break free.

Flea circuses use the same idea. Fleas in the wild can jump very high. If you put some fleas in a jar with a lid on it, they will jump and hit their heads. After a while, they want to stop hurting their heads, so they will only jump to just below where the lid is. Even if you remove the top and move them to a different container, they won’t jump higher than they’ve been trained because they think they can’t.

We aren’t elephants, and we aren’t fleas. We can train ourselves to believe in what we can accomplish even. It’s essential to believe that we can do something so that we can do it.

What exactly does it mean to believe in yourself? Can I believe that I can be a great artist even though I’m not very talented? Can I believe I can be a gold medal Olympic even if I’m not athletic? Can you please explain what you mean?

Of course, there are limitations. Suppose you are only 5’2″ (like me); the likelihood of becoming a professional basketball player is low. But you can still play basketball and get very good at it.

As far as art goes, that is in the eye of the beholder. I live in a 55 and older community that has an art club. We have an Art Show every year called “Creative Visions.” The idea of this art show is to pair the photographers with the artists to see what they come up with. The community then votes on what they like best.

Every year, the paintings that look most like the photographs win. Does that mean that the “best” paintings are the ones that look like photographs? Are those the “best” artists?

You can answer that yourself with this one question. Did Van Gogh’s art look like a photograph? Did Salvador Dali’s?

Just because someone doesn’t like something you did doesn’t mean it’s terrible.

Was there a time when you did not believe in yourself? How did this impact your choices?

I did not believe in myself in High School.

I didn’t try out for sports. I was a B student even though I could have gotten As. And I didn’t try for scholarships. This impacted my entire life until I “fell” into Financial Planning.

At what point did you realize that in order to get to the next level, it would be necessary to build up your belief in yourself? Can you share the story with us?

After I got a job in Financial Services, I started hanging around different types of people. They listened to self-help programs (these were on tapes at the time) in their cards.

I purchased my first set of tapes from Tony Robbins. These were very expensive to me then, but they set me on a journey of self-improvement.

What are your top 5 strategies that will help someone learn to believe in themselves? Please share a story or example for each.

1 . Get some friends who are doing what you want to do.

It isn’t easy to believe you can do something if you’ve never known anyone who’s done it before. For example, my friend Jenny opened me up to a world of recurring income. Before I met her, I never knew this world existed outside of Multi-Level marketing companies, which I was not interested in.

2 . If you cannot find people in your circle of friends who are doing what you want to do, find them online. Hundreds of thousands of groups are out there, some in person ( and some online (Facebook, LinkedIn, etc.). You don’t have to pay to be in a group of like-minded people.

3 . Create or join a mastermind. You can create one if you don’t have the funds to join a group. Think about the people you want to be around and reach out to 8–10 of them.

Let them know you are putting together a mastermind and what the benefits of joining your (live) or (online) group will be. If you don’t know what a mastermind group is, read Napoleon Hill’s “Think and Grow Rich.”

Your local library likely has this book, which you can read for free. Although it was written in the 30s, it still has a lot of great information.

4 . Join for $14 a month and listen to audiobooks every month that help you believe in yourself or achieve your goal.

5 . Join a paid mastermind group. Being around people who have paid to join a mastermind group can open your mind to new experiences. Seeing others achieve and getting their feedback can help lift you like nothing else.

Conversely, how can one stop the negative stream of self-criticism that often accompanies us as we try to grow?

This is a tough one. What I did was simple: When I heard myself doing this, I stopped and rewrote that script. In other words, if I was saying, “You will never (X),” I imagined myself doing it. Right then.

Right there. But I did it every time until I was able to stop those thoughts.

Are there any misconceptions about self-confidence and believing in oneself that you would like to dispel?

I don’t believe that you can think yourself to success. You must see yourself making tiny changes leading to your goal. Activity breeds success. So, for example, I don’t believe in giving trophies for showing up. Although showing up is the first step to winning the trophy, you must actually accomplish a goal that you set for yourself.

What advice would you give to someone who is struggling with imposter syndrome?

Look at the people who are doing what you want to do. Likely they also had imposter syndrome (or they still do). Set challenging yet achievable goals. As you achieve those goals, you’ll suffer less from Imposter Syndrome.

Ok, we are nearly done. You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

I want to simplify Medicare. There are many complicated rules we should eliminate (for example, Veteran’s benefits are creditable for Part D but not for Part B).

The terminology needs to be clarified. And I’d like to take private insurance companies out of the business of Medicare. Medicare Advantage now costs our country more than original Medicare. And people with Medicare Advantage are more restricted than people with Original Medicare.

We are very blessed that 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 just see this, especially if we both tag them 🙂

I’d love to have a private conversation with OPRAH.

How can our readers further follow your work online?

You can check out my site at or follow me on linked:

Thank you for these really excellent insights, and we greatly appreciate the time you spent with this. We wish you continued success.


  • Savio P. Clemente

    TEDx Speaker, Media Journalist, Board Certified Wellness Coach, Best-Selling Author & Cancer Survivor

    Savio P. Clemente, TEDx speaker and Stage 3 cancer survivor, infuses transformative insights into every article. His journey battling cancer fuels a mission to empower survivors and industry leaders towards living a truly healthy, wealthy, and wise lifestyle. As a Board-Certified Wellness Coach (NBC-HWC, ACC), Savio guides readers to embrace self-discovery and rewrite narratives by loving their inner stranger, as outlined in his acclaimed TEDx talk: "7 Minutes to Wellness: How to Love Your Inner Stranger." Through his best-selling book and impactful work as a media journalist — covering inspirational stories of resilience and exploring wellness trends — Savio has collaborated with notable celebrities and TV personalities, bringing his insights to diverse audiences and touching countless lives. His philosophy, "to know thyself is to heal thyself," resonates in every piece.