Entrepreneurship is Lonely | RTWOS EP 4 with Kaili Meyer – Shamelessly Ambitious Episode 129

Filed in All Episodes, Business Strategy, Emotional Intelligence, Leadership Development, Releasing The Wounds Of Success Series — November 21, 2023

Entrepreneurship is a freaking rollercoaster. It’s filled with moments of self-doubt, isolation, and triumphs that make you want to pat yourself on the back. Kaili Meyer, shares her experiences on the entrepreneurship rollercoaster in this episode. This is episode 4 of the Releasing The Wounds Of Success Series, & we’re diving into the complexities of being an entrepreneur and just how lonely it can get.

Kaili, a talented designer and the missing puzzle piece inside my business ((AKA my new copywriter which I am SO over the moon excited for all the magic she’s created for me)) hopped on the podcast to talk about creating and losing relationships, specifically friendships, as an entrepreneur. If you’ve ever felt alone in this space or like you can’t relate to your corporate friends, this is the conversation you’ve been waiting for. Follow Kaili on Instagram and find all of Kaili’s resources here. FYI: I bought every single one of her templates and they have been a game changer for my business.

Embracing the Rollercoaster

The entrepreneurial journey is often described as a rollercoaster, and it’s a rather fitting analogy. There are moments of holy-shit-exhilaration when you feel like you’re on top of the world, and there are moments of sheer terror when you wonder if you’re even cut out for this. High-highs, and low-lows. If you’ve ever thought you’re crazy for having these two extremes, it’s perfectly normal and it’s something we ALL experience.

The Six-Month Spiral

Kaili shared about her “six-month spiral” to describe those moments when it feels like everything is falling apart. She shares that her & one of her close industry friends text each other about twice a year to check in and say they’re on their six-month spiral. It’s a moment when self-doubt creeps in and they question their abilities. It’s a time when the inquiries have dried up for only four days, and they question their competence. I find this so relatable because it seems that once the engagement falls or the work-with-me requests stop coming in, we think we’re complete failures and want to throw in the towel. But through these ups and downs, I’ve learned that entrepreneurship is a journey of self-discovery and transformation, && it’s crucial to redefine success on our terms. These spirals are just a reminder that entrepreneurship is unexpected and it can be a lonely, isolating, and overwhelming road if you’re not proactive about combating these feels. 

Facing Rejection and Loneliness

During our conversation, we touched on the topic of rejection and loneliness. It’s common for entrepreneurs to feel the weight of rejection and the isolation that can come with it. It goes back to Maslow’s Hierarchy of Needs and the truth that belonging actually lives really high. In fact, in our history as humans, in tribal times especially, if we were to be rejected or removed from a tribe what would happen is that we would feel as though we were going to die. Maybe that sounds extreme, but as humans if we don’t have people around us creating connection, there’s no survival. Fast forward to nowadays, even though now we’ll be fine & survive if we get rejected from a friend or loved one, we literally still feel as though we’re going to die. I can attest to this right now as I’m in the middle of a very heavy friendship breakup that has manifested itself into physical symptoms. It’s a lot to go through. Especially when we feel straight up rejected.

Sometimes, this loneliness isn’t completely due to rejection, but also can be self-created because we’re afraid to make others uncomfortable with our emotions. As entrepreneurs, we often push ourselves to the side, our problems fall, and we don’t talk about our lives because it can be hard for others to relate and we desire to keep everyone comfortable. However, it’s crucial to understand that if we want deep connection & friendship, we have to separate entities from our business endeavors because we are more than who we are as entrepreneurs. 

Finding Support in Unconventional Places

As high achievers, it can often make others uncomfortable to the point of them not wanting us in their lives. This feeling is like no other, but one of the most surprising and fulfilling aspects of entrepreneurship is the incredible friendships that can be formed online if you’re open & intentional with the possibility. Kaili shared about connecting with people she’s never met in real life but FaceTime’s multiple times a week. Those friendships have become an integral part of her life! You see, online friendships can be just as meaningful and supportive as those in the physical world. Whether it be with friends in your local community or in the online space, it’s so important to make connections so we can feel supported in our journeys.

The Assumption of Abundance

There were many nuances that emerged from our conversation around friendships, but one was the assumption that entrepreneurs with a thriving online presence and many connections don’t need additional friendships. Have you ever been told by a friend that they didn’t think you needed them because you already have enough friends online? I have and to me, it makes no sense. Past friends of mine have literally said, “it appears that you have so many friends online that you don’t need us.” It’s interesting because, yeah, when you’re willing to put yourself out there, connect, and befriend people rather than staying in your own little tiny bubble, there are a lot of opportunities out there. The more connections, the better. Being open to new friendships and conversations is a fundamental part of personal and professional growth. However, if your “real-life” friends are giving you that excuse, maybe they are looking for a way out. Don’t spend time trying to mend friendships if they aren’t celebrating you as much as you do them.

Treating Online Friendships as Real Ones

Additionally, it’s so, so important to treat online friendships with the same care and attention as the “real life” physical friendships. Engage in meaningful conversations beyond business matters and show a genuine interest in each other’s lives. Being a supportive friend can lead to incredibly rewarding relationships. I will probably have this engraved on my tombstone, but humans crave connection && we all want to be liked. If we showed a little bit more interest in who people are rather than what they do for a living, we would find a much deeper connection.

The important thing to remember is that entrepreneurship is a journey filled with highs and lows, self-doubt, and self-discovery. The key is to recognize that, yes, it can be a lonely road at times, but it doesn’t have to be isolating. If your physical friendships fall out because you are “too much,” I’ve been there sister, and I feel so deeply for you. I encourage you to find meaningful online friendships and embrace redefining success. One of the best ways to do that is to “put yourself in the room.” You can do that by joining my mastermind, REDEFINE. It’s a mastermind where tailored business strategies get a therapeutic edge pairing emotional wellness with a customized approach that meets you where you’re at and takes you where you’re going. This mastermind is full of women who get it because they’re high achievers, too. If you’re craving a deeper friendship where the person on the other side sees you for you, not for your CEO title, come join us. We’re about to take our businesses to the top together.


This series is equipped with an additional email that goes along with each podcast episode that gets a little bit deeper with additional therapeutic action steps so you can release your wounds, too.


The Hybrid-Mastermind Experience where tailored business strategies get a therapeutic edge — pairing emotional wellness with a customized approach that meets you where you’re at and takes you where you’re going. Applications are open now to WAITLIST members only. It’s not too late to jump on the waitlist for yourself: JOIN NOW.


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