087: Jen Kirkham | Turning Your Failures into Success and Weekly Check-ins on Your 90-Day Goals

Jen Kirkham is a well-known insider to a multitude of networks. From healthcare, finance, coaching, and online education. Jen is an Operations Guru that connects the dots for growth and scaling businesses for high-level executives. Jen has a selective approach to the clients that she serves. She has partnered with Emma Mersetter to curate and leads mentorship programs for virtual assistants to establish, maximize, and cherish their careers with a successful pathway.
In this episode, Jen talks about how you should have a 90-day goal with weekly check-ins to see real impact. Jen explains why integrating something already in your life to be successful is vital, and she challenges the belief of how learning from your failures is only part of the way to get to where you want to go. Check it out!

[02:17 – 13:02] Turning Your Failures into Success


The Mastermind Effect:  02:05

Let’s dive into it. Our ability to learn and take in information had drastically changed in the last 10 to 15 years. When you and I were younger, it was textbooks, educators, friends, family, and coworkers, but that’s a sliver of what’s possible. How has your learning changed from your early years versus today?


Jen Kirkham:  02:40

As I’ve gotten older, I’ve realized that some of the beliefs of things that I think are possible have been debunked by either technology, my family culture, how I was raised, or how they were raised was passed on to me.  Then, I’m like, “Well, wait a minute, I can do more than what’s possible.” Whenever I speak with those who have known me for over 10 to 20 years, they think I am changing. But what’s changing is my beliefs of what I think is possible, what I think I can achieve, and what I can help others achieve.


The Mastermind Effect:  03:16

That’s the thing. It’s allowing and saying, “Hey, I might have been brought up this way, I might have trained, I might have learned it this way.” But when someone else comes along, you’ve saved room to sit there and challenge those rate-limiting beliefs to sit there and say, “Hey, I’m going to exchange this now for something that makes more sense and helps me move the needle forward in what I’m building.”


Jen Kirkham:  03:40

The key point is the only time that you realize that your past beliefs aren’t true for you today is that there’s either a success experience or there’s a failure experience. It’s your interpretation of that experience that propels you into challenging those beliefs and making a new truth to what’s true today.


The Mastermind Effect:  04:03

We learned so much from our failures. We shouldn’t let our past failures define our present and our future. We use that past failure as a crutch instead of using it as how do we reframe that. How do you take a failure or a misstep? How do you reframe that to change your present and your future?




Jen Kirkham:  04:25

That’s an excellent point. I’m going to challenge a common belief. A lot of people say it’s through our failures that we learn to change or success. I actually disagree with that because if we have recurring failures without having those minor shifts, having minor successes, identify what needs to change and have a different kind of failure. If we fail the same way over and over, we’re going to continue to fail. and say, “Oh, I’m learning from my failures.” But what are you learning? You’re learning to do it over and over again. To have your failures turn into success, you must have someone by your side that had failed like you have before and changed one degree in their trajectory to get a little bit different result.


There are two rules of the mind that I follow every single day. The first rule is that the mind does what it thinks it wants you to do. Your thoughts make your reality. The second rule of the mind is that your mind loves what’s familiar. If you’re looking to turn your failure into a success, your success has to have some common ground for what you’ve done before.  Whether it’s hanging around the same group of people for a period of time, you start to act like them and make some more successful decisions; or you change your physical environment to make something better and more familiar so that you can continually make those changes. That’s the end result. What 2020 has taught us is things can change on a dime, and monumental shifts don’t have to take a long time.


The Mastermind Effect:  06:21

We have to remember that things will change without our permission or without welcoming them into our lives or our household. It’s going to happen from now to the end of time. Change is the only constant thing.


Jen Kirkham:  06:35

I’m okay with change unless it’s too frequent.


The Mastermind Effect:  06:41

Talking about learning, we have more ways to take in information than ever before, and it can be confusing. We got all these platforms and all these people telling you what to do. Some people look for a mentor, a coach, accountability buddy,  mastermind, and other different ways to take in information and learn. Who are you currently learning from? And more importantly, how did you connect with them?


Jen Kirkham:  07:19

That’s a really good question. A lot of my connections today are relationships that started five years ago. I approach new relationships today differently than I did five years ago. Ever since I’ve learned the concept of social networking and being of service, my relationship begins with making a human connection and finding common ground that we have core beliefs. My core beliefs start with integrity. I’m attracted to someone who has personal integrity, business integrity, and service-centric. The things I’m learning now are like my core values. I’m learning from people who have taken that level of integrity and mapped it out into other areas of business or areas of their life.




The Mastermind Effect:  08:22

I love how you talked about how you started planting the seeds five years ago. Where the relationship was and where it’s at now are two different places and how you go about it today is different. It is important that you want them to align with your mission, vision, and values and have a symbiotic type relationship; because if not, you’re going to have that friction.


Have you ever had where it’s like, you want something to fit, but you keep fighting and keep coming up with that constant sandpaper effect because of your beliefs? What was it taught you?


Jen Kirkham:  09:03

It’s usually around project management, whether it be like you’re working together with a team and someone with a different objective, and usually, egos involved. I’ve got an ego.  I like to look and feel good. I want to be heard and understood. Everybody has that to a certain degree. When it starts driving the train, that’s where I cut the line and be like, “if your ego continues to drive the whole thing and it becomes all about you as an individual looking good, and everyone else suffers, then then I’m not okay with that. I’m also okay with you doing that, and I’m not attached to how you approach it.” I think that’s the key differentiator because I still am good friends with people that operate that way, but I choose not to operate the way that they operate, and I learned different things from them,


The Mastermind Effect:  10:02

it’s a win-win right there and how you’re still able to keep that relationship. You’re both still able to work off or feed off and learn from the other person. Even if they don’t match with that. You’re not giving them an ultimatum.


Jen Kirkham:  10:22

Believe it or not, it starts with who you are inside. That’s where the integrity piece comes in. When I was growing up, I heard that integrity was like doing the right thing when no one’s looking. I think that’s only surface level. Integrity goes so much deeper than you’re doing what’s expected of yourself daily; you’re doing what’s expected of others daily. You’re doing what’s expected with your business, like, do you deliver on what you say you’re going to deliver on? It’s all about keeping the main thing and being core to that. That’s why I can maintain that relationship with those who have to operate differently than I do because they know what to expect of me, and I know who I am,


The Mastermind Effect:  11:09

No matter what day of the week is, it ends in why they know what they’re going to get from you and what you’re building over there. Staying on the subject of people, I feel that we get stuck. Sometimes we don’t know how to execute what’s in our head. We’re still going through a pandemic, and I think this amplifies that in some form or fashion. It also allows us to reset and rethink how we want to accomplish things and what is important. How masterminds and coaching help you when you’re looking to reset and reshift how you want to accomplish what you want to do?


Jen Kirkham:  11:50

I love masterminds because they’re typically an experience that provides a roadmap with a clear point A and a clear point B. When you’re with a group of people who are going towards their point B, it doesn’t always have to be exactly your point B. If I want to make a certain dollar amount, not everybody in the group will have that same number, but their goal is heading towards that number for them. A mastermind is a way to set our own point B’s and have a road map of someone who’s done it before. We accelerate our success, and our success is what defines us.


The Mastermind Effect:  12:30

It is nice when it comes to a mastermind, learning how other people who have already seen around that corner and you can take advantage of their previous missteps or previous successes. You had touched on that earlier of how important it is to utilize those people around you and learn from their successes and learn from their failures, so you don’t continue making that same mistake.


[13:03 – 22:32] Self-Education and Elevating Insiders


The Mastermind Effect:

Masterminds have been around for a while. The first one was the apostles. Then Benjamin Franklin creates the Judo Club or the Leather Apron Club, and Napoleon Hill writes a book about it. There seems to be this large boom of self-education over standardized education and how we’re waiting out what’s important. Where do you see the shift going between standard education and self-education going forward?


Jen Kirkham:  13:41

For this, I have to tell you a story. There is a  couple that recently enrolled in the MBA program. Enrollment in MBA programs has skyrocketed because institutions recognize everyone is going virtual, and they wanted to keep enrollment high. They eliminated the entrance exams, lowered the tuition fee, or offered more flexible payment programs.  It made getting into these traditional institutionalized programs easier. These two people enrolled in the program at this great university. The professor lets them work on their projects together, and the couple does half the work, but they both get the grade. Meaning they don’t work on their areas of expertise, maximize their strengths and learn new talents, and the professor’s okay with that. In other words, mediocrity in institutionalized programs is teaching theory not as much application. Those people are being disserved. There’s my little soapbox on the platform.


If you are currently in the MBA program and listening to this, I encourage you not to go towards its mediocrity. Instead, look to the self-education approach to your traditional program. With self-education, you can get a quicker result and learn faster from people to have interactivity. Apps are available nowadays, where you can have a conversation or be part of the inner circle conversation that you would have never dreamed of.


The Mastermind Effect:  15:46

We talk about this pretty frequently on here, especially with what we’re building with the Success Finder. Standardized institutions are looking to create a profit. The fact that you have two people paying the said price, and they’re not able to go beyond what they already know because they’re able to tag team one project and get two of the same results. What does that say? Is the institution or professor concerned about what they’re learning and what they’re able to implement then? Are they just wanting to cash the check?


Jen Kirkham:  16:28

For those who pay and invest in themselves in the masterminds that we do, I am vetted for their success.  I have an investment in them with my time, the resources that I’ve worked hard to find with the tools that I’ve made my own. I encourage them to make these tools their own. That’s what sets us unique: being able to say, guys, we’ve studied the success experiences you need to have in this space. Now that you know one, two, and three, you should be able to do this. We’re not going to take an exam because words are words, and you can speak the same words and even do some thought repeating. But what about that experience? What was it like? You get to talk about the emotions that happened at certain phases, and that transformation is priceless.


The Mastermind Effect:  17:16

Since we’re on that, let’s go a little bit deeper into there. Typically, when someone invests in their future, they have a better than a vague idea of what they’re going to get. They have an idea of what the outcome could be. What should people expect when they go through your mastermind or your coaching and what you guys are building? What’s the reality of working with you and your partner?


Jen Kirkham:  17:39

The reality is that we expect you to take action and that all of our interactive conversations are around the action you’re taking. We have a course that complements our journey. You can watch and download some tools. You can say all the right things, but we’re going to talk about the experiences that you have.  We guarantee that during our one-month experience together, you’ll have one crucial experience that will change your life.


The Mastermind Effect:  18:07

You’re like, “Hey, listen, if it’s for 30 days, what we are promising is at least one crucial breakthrough.” I want to go a little bit deeper on that one. Because when I think about someone hiring the right coach or being in the right mastermind, I sit there and see how the marketers are marketing the good coaches and masterminds. They transfer the risk because they don’t implement what they’re teaching. They don’t have a coach or a mastermind themselves. How do you keep yourself from transferring the risk to your clients and giving them the tools they need to be successful?


Jen Kirkham:  18:49

That’s a great question. I’m in the trenches doing the same thing. The things that I’m teaching those in the mastermind are what I’m doing with my clients. I also have a coach that I’m accountable to. Every aspect of my business with a mastermind with a course, I take personal responsibility. I know that I’m not an expert at anything. There are some areas that I haven’t mastered, and I’m still working on. I’m honest.  I know just through the power relationship, I’m going to learn from those in the mastermind, as well. I just don’t see any downfall here. When choosing a coach or choosing a mastermind to attend or learn from, select the ones with a clear success experience outline: What are you going to experience, not just what you’re going to learn? What can you do because you learned it? Does that mastermind leader attend a mastermind? Do they have a coach?




The Mastermind Effect:  19:47

That’s important. One of the first questions: Who’s your coach? What mastermind are you in? Who are you continuing to learn from? If they don’t have anyone right now, that should be a big “X.” That scares you because they’re not investing in themselves. How can they continue if they’re not willing to invest in themselves? The most important investment is yourself because you can control the outcome most of the time, excluding COVID.


Jen Kirkham:  20:13

It’s the end of experts. The curse lies with the teacher that has too many answers. The power lies with the student asking the right questions. That’s how the teacher presents itself when the student is ready.


The Mastermind Effect:  20:36

We’re talking about success. I feel that people have a way of surprising us all the time. The rooms you put together and the people you work with, your hand-selecting them, you’re curating them, and you’re making sure that they check certain boxes and their beliefs. Has anyone who has been through your mastermind or your coaching that was able to surprise you? And in turn, what was the outcome because they went through that? What’s the success story?


Jen Kirkham:  21:14

There are two that I want to outline. One is a teacher in the public education system, and the other one is a brilliant stay-at-home mom. Their experience and drive are very similar. From two completely separate walks of life and two completely different backgrounds, we didn’t pay anybody in a box. The boxes they’re checking are more about their drive and desire. We’re looking for clues on how well they’re ready to take action rather than their background, work experience, and resume.


The teacher struggled in 2020 to maintain her position. She was the leading teacher figuring out all of the technology nuances. When she went back and reported to her superiors, there was no reward. Mediocrity was the norm, and she wasn’t okay with that. Now, she’s transitioned into a role. Before the mastermind was complete, she onboarded her first client and is currently working with her clients. And we’re supporting her with that and helping her with those how-to’s.


The stay-at-home mom is a support system for her husband. They’re running their e-commerce business. Instead of curating clients, she’s supporting her husband and their family business in a new way. Then, just two days ago, she surprised me and said, “Jen, I think I want to do some strategic business consulting, and I’m a good manager.” She has six kids. She’s a great manager because I go to her house, and it’s not perfectly clean everything, but everyone knows her expectations, and she can problem-solve, like nobody’s business. I’m like, “I look up to you. I want some of your management skills.”


The Mastermind Effect:  23:04

It’s beautiful when you can impact the people that are already in your circle. You can see that immediate effect on someone just that taking the chance to invest in themselves, and in turn investing in what you and your team can help them grow to become successful or bridge that gap between where they’re at and where they want to go.


[22:33 – 29:11] Creating Success


The Mastermind Effect:

There are a lot of things that it takes to be successful. We’re building a company around the Success Finder.  On my solo shows, we talk about what it takes to be successful.  Several parts include willingness to fail, partnerships, experimentation, mentorship, coaching, and all sorts of things. What do you believe is a key factor in someone’s success?


Jen Kirkham:  24:04

They’re stretched to success that maybe they didn’t seem possible for themselves and let it integrate in something familiar that’s already in their life to continue to grow in that success. That means they’re helping define it, and they’re entering new possibilities. Feeling uncomfortable is okay, but you can accomplish more with a support system.


The Mastermind Effect:  24:28

I like that you integrate something already in your life to be successful. It’s something familiar you’re probably already passionate about, or at least you hope you are. A perfect example is probably the stay-at-home mom, who’s got six kids. She’s already integrated something into her life, and now she’s able to take her passion for what she’s good at and turn it into something. Thanks to you. That’s awesome.


We’re coming closer to the end here. I think there’s always new ideas brewing in times of prosperity. It’s easy to be successful when everybody’s winning. As the world’s a little bit different now, innovation and ingenuity come when we feel the squeeze. We’ve been feeling the squeeze for a while now. What are you working on right now that’s going to take place over the next 12 months that excites you?


Jen Kirkham:  25:18

I want to share something specific that I’m working on—one with one of my clients and then one with our insiders mastermind. One of my clients is world-renowned doctors for a specific treatment. They’ve been in the traditional institutional learning. They’ve been lectures on the lecture circuit and have books and everything. We’ve known each other for over five years. The reason why they circled back is they recognized that learning happens differently and that the doctors who want to learn from them don’t want to go to their lectures. But we’re using the mastermind learning style in more traditional settings. Large universities are also starting to follow that path. That’s something super exciting. I get to apply IO psychology and business tools and learning styles into a new way of developing online courses. It’s something completely different and exciting.


With the insiders, we are continually having conversations with those who have gone through our program and other people who do what we do. We’re refining what we call the “insiders’ edge” into collecting the success experiences that you needed at this phase. That’s going to be a continual refinement throughout the year. I look to learn a lot and see how I can refine the insiders’ edge process and help my clients be on the fast track to success.


The Mastermind Effect:  27:08

I love that depending on what phase you’re in, here’s where you need to plug in this piece, this person,  or this process to take you to the next level of success and just saying, “Hey, we’re going to continue to refine this. And we’re going to continue to add to this.” That’s awesome.

Last one for you. What is a tip, a tactic, an actionable item that if someone listening today implemented this over the next 30, 60, or 90 days, would see a real impact on their personal or business life?


Jen Kirkham:  27:40

90-day goals and weekly check-ins with somebody that really will tell you the truth. That tuned into your habits and what will move the needle for you, whether personally or professionally. Make sure that weekly check-in is tuned in to the 90-day goal. Every single day is taking a step towards that 90-day goal.


The Mastermind Effect:  28:03

Yes, because if it’s taking you away from where you want to go, it’s taking you away from the shortest distance between where you’re at and where you want to go.


Jen Kirkham:  28:18

It’s the simplest thing to do, but it’s not the easiest thing to do, and it will make a difference.


The Mastermind Effect:  28:24

Sometimes the simplest things are the hardest things. I’ve learned so much today. I’ve got some notes on this. We have the founder of Elevating Insiders, Jen Kirkham. I appreciate your time and everything that you gave us today. Thank you so much.


Jen Kirkham:  28:42

It’s an honor and privilege to be here with you, Brandon. Thank you.

Tweetable Quotes:

“If we fail the same way over and over, we’re going to continue to fail. So in order have your failures turn into success, you must have someone by your side that has failed like you have before and change one degree in your trajectory to get different results.” – Jen Kirkham

“With self-education, you can get quicker results. Learn faster from people in a way that you can have interactivity.” – Jen Kirkham

“It’s the end of experts. The curse lies with the teacher that has too many answers, and the power lies with the students asking the right questions. That’s how the teacher presents himself, when the student is ready.” – Jen Kirkham

“From now, till the end of time, Change is the only thing that’s constant.” – Brandon Straza

Resources Mentioned:

Connect with Jen and Elevating Insiders, send an email at elevatinginsiders@gmail.com. You can also visit https://elevatinginsiders.com/ 

Be one of the early adopters of The Success Finder! Download it from the App Store or Google Play Store.

You can connect with me, Brandon Straza, on LinkedIn, Instagram, or send me an email at brandon@thesuccessfinder.com. I’d love to get in touch and talk more about personal development and how you can live past beyond your limits.

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