The Highs and Lows of Being an Entrepreneur

blog business tips for entrepreneurs entrepreneur entrepreneur business coach female entrpenreurs fempreneur mompreneur side hustle Jun 08, 2021
Holly Haynes

I recently was interviewed for Thrive magazine talking about the highs and lows of becoming an entrepreneur. I wanted to dig into some of those as I think it is so important to address both the positive and the not-so-positive. This blog post is a little different as it is personal. And shares some real-life behind-the-scenes. 

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? 

If you are new here, thank you for hanging out with me! I thought it might be helpful to share my backstory before I shared the ups and downs.

Prior to the pandemic I was working full time for a non-profit (and still do) and was dabbling in starting my own strategic coaching business. I also had a wellness accountability business I was running, but it wasn’t 100% in alignment with my long-term goals. (I was “working” on a lot of things, but wasn’t focused). I knew I wanted to pivot but wasn’t sure how, or when the right time would be. I needed to niche down. And make sure that when I am working on my business, I was working on the right things.

Without knowing the pandemic was going to be as intense as it is now, in January of 2020 I decided my next step would be to start a podcast geared towards women running a business who were also working full time. I love to teach and had the background to be able to help a lot of women with their business strategy. This was my step to streamline my businesses and niche down my focus. Ironically my very first podcast episode came out the 2nd week of March, the week almost all of the US shut down due to Covid-19. To say I was panicked was an understatement. I am an Enneagram 3 and like things to be perfect and to please people. This was not ideal, not to mention getting on social media to chat about a new podcast called “Crush the Rush” (how to run a business without it running you) just seemed insensitive when many people were losing their jobs or being laid off.

I continued to quietly grow the podcast and realized that a lot of people were looking to start their online businesses because they had been laid off. Even though it wasn’t at the scale I had planned, I kept going. And all of a sudden, I had a podcast that was not only growing, but helping women build their “side hustle” as I call it, in the middle of a pandemic.

This podcast gave me the credibility I needed in a time of uncertainty for people to trust me which in turn allowed me to scale my business very quickly. Now I run a full-time coaching business while working full time from our home office in Columbus, Ohio.

Let’s dig into the actual highs and lows and lessons learned. The journey of an entrepreneur is never easy and is filled with challenges, failures, and setbacks, as well as joys, thrills, and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it.

I think the biggest challenge I personally have had is you are never done. There is always something that can be worked on, created, improved, etc. You always wish for that extra 24 hours. 

Most women who start a business are looking to build a business for time freedom and flexibility but because they don’t have the skills or experience in entrepreneurship, they end up spending all their time working and burning out. The challenge is knowing when to slow down and when to speed up, knowing that you are in this business for the long term. (i.e. you can’t work 24/7 for the next 10 years).

I feel like as an entrepreneur you celebrate your wins a little more closely than perhaps in the corporate world. A few extra sales are more personal. It means a family vacation or actual tangible things that can impact your life and your family’s. A paycheck from a 9–5 feels a little different as it is expected and planned. Because of that, there are extreme highs and lows as an entrepreneur and I would say most of them are driven by financials. Ultimately building a business with passive income so the highs and lows are a little less intense is the goal.

Want to hear an actual win? Maybe you can relate. 

My biggest win was launching a mastermind coaching program less than a year into my business successfully, selling out without a formal marketing campaign and small email list. My clients were asking for it and I listened. I crafted a program that was exactly what they were asking for, targeting their specific challenge and built in the strategy, productivity, accountability, and community I love and believe you need as part of your business model. It was different. I am not sure most people thought it would work. My husband also thought I was a bit nuts for about two months. But in the end, it has been a turning point in my business. It is now my signature program and I have a waitlist for the next round. It reminded me to trust my gut.

Now let's talk about lows.

One of the biggest lows I had in my business was this past year over Black Friday. I had never done any sort of Black Friday launch before so I decided I was going to create a mini-course and launch it over the Thanksgiving holiday. My first lesson learned was creating a brand new course (while also working full time and managing a family) over the holidays was a mistake. My priorities were not aligned. I was burnt out before I started.

The second lesson learned with this during Black Friday you are competing with every single corporation in the world. I was small potatoes and did not stand out.

After the Black Friday experience, I took a step back and really looked at my strategy. It made me realize that I wasn’t serving at the right level. So I redid my product roadmap, dialed in my vision, and launched a mastermind a few months later. It was my most successful launch to date. You really can learn from your mistakes. So I am grateful for that experience.

How can you navigate the highs and lows? You know I made a list! Here are 5 things you can focus on. 

1.Your why and vision should be so strong it literally holds you up when you fall.

  • You can read pretty much every business book on the market and they will all tell you to create your why. But have you really sat down the pen to paper to write it out? 

  • Your to-do list will never be complete. Simply being comfortable with never being complete with all your projects is a big mindset adjustment. That is why it is so important to use the methodology of the CAKE method (or 3 things).

  • Your support system should be a circle of mentors that give you feedback but also positive reinforcement. Joining a mastermind and finding and hiring mentors that were 1–2 steps ahead of me has been a game-changer for my business. I also see it as a game-changer for my clients. You cannot do this alone. Find your squad. 

  • More work doesn’t always mean more income. Think about time freedom instead of time management. Ask yourself this. Are you busy working on the right things? Or are the right things getting missed because you are busy? Your strategy and focus matter. 

  • You only need to help one person to make an impact. When you feel like you aren’t making a big enough impact, remember who you have impacted so far. I love the quote, “To the world, you may be one person, but to one person you may be the world” You can change the world one person at a time. Be grateful for those you are able to serve.

I personally think resilience is not giving up. I always say you can change the plan but you shouldn’t change the vision. Sometimes the path looks different but that is OK. You have to choose to keep going.

I hope this inspires you to continue telling your story and sharing your gifts. You can read the entire article including some additional behind-the-scenes here!

Looking for more details on this topic?! Check out the Strategy Lab in the Crush the Rush Club!


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Holly Marie Haynes is a business strategy coach, podcaster, mom of twins, and founder of the Crush the Rush brand. She helps women create simple scaleable offers and systems to grow to multiple 6-figures.

Holly Marie Haynes is a business strategy coach, podcaster, mom of twins, and founder of the Crush the Rush brand. She helps women create simple scaleable offers and systems to grow to multiple 6-figures.

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