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My Biggest Business Regrets I’ve Never Shared

June 12, 2024

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Being an entrepreneur means I’m always learning… and sometimes that hindsight really is 20/20.

Every business journey comes with learning moments, and sometimes we have to go through it in order to get that breakthrough or aha moment! 

So, looking back over my experiences, strategies I tried (and didn’t try), I’ve got a handful of things I regret from my business journey – and in this episode, I’m sharing them with YOU!

Because that’s the heart of Goal Digger (and always will be): I’m here to talk about the good, the bad, and the ugly because I want to help YOU see the growth you deserve… and skip as many of those ‘regrets’ as possible.

So let’s dive into the things I regret in my business journey that inform my decisions as I keep moving forward!

Regret #1: Not Having Boundaries

One of my initial regrets was diving into entrepreneurship without setting clear boundaries. Juggling a full-time corporate job, I found myself heading towards burnout due to the lack of balance.

While I have since learned to set boundaries, I wish I had done so earlier to avoid the exhaustion and overwhelm I experienced!

If you need help with this too, check out Episode 758: Weird Places You Need to Set Boundaries in Your Biz!

Regret #2: Hiring Too Slow

I don’t think many of us start a business imagining that someday we’ll be a boss. Generally speaking for many, it’s a solo endeavor to get things off the ground but then you realize that you need help and that can expand into a role you didn’t even really imagine. 

I’m the queen of white-knuckling things or doing it all myself and over the course of my business journey, I’ve definitely been slow to hire. I’ve never wanted to have a huge team, and I don’t want a lot of overhead costs… But that being said, I DO regret not hiring help sooner in my business journey. 

As a solopreneur, I took on multiple roles, hindering growth and causing unnecessary stress. Over the last few years, learning to delegate and build a team has been crucial in alleviating burnout and allowing me to focus on what truly matters!

Regret #3: Blurring Personal Brand and Personal Life

If you had asked me even a few years ago if I think everyone should have a personal brand, I would have undoubtedly said yes. 

My initial desire was to connect and build community online due to the lonely road that building your business in those first few years brings; which is what I would think partially supported this evolution into blurring the lines to begin with. 

There’s so much power in the personal brand, but there’s also limitations and expense. While personal branding is powerful, I regret not defining clear distinctions between my brand and personal life sooner to maintain authenticity and balance.

Regret #4: Operating From Masculine Energy

This is a big topic in my life right now because recently in therapy, I realized I have been operating from a place of force and hustle, neglecting the flow and ease needed for sustainable success.

Nwo, I’m embracing a more balanced approach between masculine and feminine energies, which has been transformative in finding peace and joy in my entrepreneurial journey. This means that my team and I have been slowing down output, protecting the schedule, and leaving more room for margin. 

This is important because as you grow your business and eventually hire a team, you have to lead by example. If churning things out like a machine nonstop, your team will also adapt to that and regardless of what you say about workplace boundaries/expectations, they will watch and follow suit. So the internal work has external impact as well.

Regret #5: Not Prioritizing My Health 

Neglecting my health in pursuit of business success is a significant regret of mine. 

Realizing the importance of self-care and well-being has not only improved my energy levels but also enhanced my overall productivity and fulfillment in both personal and professional aspects.

I genuinely didn’t know it was possible to feel this good, I didn’t know I could have this energy and feel this way!  If you want to learn more, here are some of my favorite health-related episodes:

You can also DM me “HEALTH” on Instagram @jennakutcher and I’ll send you my favorite health resources, too!

Regret #6: Lack of Clarity and Data 

One of my biggest business regrets is that I waited for over a decade to really gain the insight I need into my business to truly understand what’s working and what’s not.

Over the years, my team and I created all of these systems and they’ve worked so well but also in turn created this rhythm that we’ve just blindly followed when it comes to content without ever really asking: Is this ALL worth the effort? Is it REALLY moving the needle?

By incorporating specific data and clarity into my strategies, I have been able to optimize processes, make informed decisions, and drive growth more effectively.

For more detailed insights on what we’re tracking and how, listen to Episode 762: From Data to Direction: 5 Interesting Insights from Our Biz Numbers!

Regret #7: Not Partnering With Aligned Values

Partnering with individuals whose business values did not align with mine was a regret I learned from. Understanding the importance of shared values and ethical practices in collaborations has been essential in maintaining integrity and serving my audience authentically.

When I partner with someone, I want to know that I can trust that they will take care of my people and get the outcome they are after.

I REALLY do share offers that I myself have gotten results from or taken value away from! Now, I always make sure I’m sending my audience to people I trust.

Regret #8: Chasing The Wrong Things

At times, I found myself chasing goals that did not align with my true purpose, leading to feelings of emptiness upon achievement. 

My definition of success is vastly different from others in my industry and so a lot of times I can feel like I’m broken or off or wrong.

Through diving deeper into my human design, I have learned that I can easily take on other people’s emotions or ideas and trick myself into believing they are my own when they aren’t, so I now have to pause before committing to things. 

Learning to pause, reflect, and align my actions with my values has been instrumental in finding fulfillment. Instead of asking myself, “What is my purpose?” I have been asking, “What is the purpose of this season?” This helps me stay away from getting “shiny object syndrome” and staying true to my path.

Regret #9: Creating An Echochamber Unconsciously

One of my regrets is that I can often surround myself with people who think like me, look like me, and operate like I do and I honestly didn’t even see that blindspot in myself until someone pointed it out. 

In today’s world, we’re so quick to curate what we consume that we can start to believe that surely everyone agrees with what we believe and that everyone operates and thinks like we do. The world feels more divided and dangerous than ever but we often just try to block out the noise from the opposing sides or from differing beliefs. 

I hate that I missed out on learning from other people, other cultures, other histories because I was so engrossed with what I knew. I can now acknowledge that I don’t know what I don’t know but I think it’s important to be open in  your thinking, be challenged by others, and to really try to expand your consciousness by welcoming different people, different perspectives, and different outlooks into your life. 

Final Thoughts

When reflecting on our entrepreneurial journeys, it’s inevitable that we encounter decisions, actions, or missed opportunities that we wish we could redo. But I want to remind you that without these mistakes, you wouldn’t be EXACTLY where you are today!

So although I think it’s important to learn from our past decisions that didn’t work in our favor, I also think it’s important to honor our journey in its entirety… because you are exactly where you’re supposed to be! 

While we can’t change the past, we can use the lessons we’ve learned to shape a more intentional and fulfilling future. I encourage you to reflect on your own journey, embrace the lessons learned, and continue digging towards your biggest goals!


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Before you get any further... Hi! I'm Jenna Kutcher!

I’m an expert at online marketing, a nerd when it comes to the numbers, and my obsession is teaching others how to make a living doing what they love (without it taking over their life).  One of my favorite places to be is here, sharing what I'm learning with you. I'm glad you're here!

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