Holly Haynes: “Your why and vision should be so strong it literally holds you up when you fall”

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? When the going gets […]

Thrive Global invites voices from many spheres to share their perspectives on our Community platform. Community stories are not commissioned by our editorial team, and opinions expressed by Community contributors do not reflect the opinions of Thrive Global or its employees. More information on our Community guidelines is available here.

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? When the going gets tough, this is what keeps you going. It needs to be ironclad. I read mine every morning. It is the screensaver for my laptop. It is framed above my desk. Make it visible.


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? In this series, called “How To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur” we are talking to successful entrepreneurs who can share stories from their experience. I had the pleasure of interviewing Holly Haynes.

Holly helps female entrepreneurs take back control of their time with proven productivity techniques, systems, and structure to create a strategy that scales long term. An industry expert, host of the Crush the Rush Podcast and featured Thrive author with a 20-year business consulting background with Fortune 500 companies, Holly runs her strategic coaching business and the Crush the Rush planner company while raising her twin daughters with her husband in addition to working for a non-profit in Columbus, Ohio.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

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 most 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. What happened, that I didn’t expect, was more women started reaching out asking me how I was running my business. So I used my podcast as a platform to teach. Every episode my focus was, how can I help more? I answered the questions they were asking, listening to my audience. I found guests that could bring in expertise. 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.

My 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.

What was the “Aha Moment” that led to the idea for your current company? Can you share that story with us?

There are a lot of productivity and strategy experts out there. My biggest aha moments still come today when the one thing everyone always asks is how to balance (insert something about virtual school, twins, working full time, etc.) with running a business. It reminded me that sometimes women want to hear from other women that are 1–2 steps ahead of them. It is more relatable. On social media, you see my kids while I am creating my courses. On my podcast, I tell you I am recording in my basement at 6 am because that is when it is quiet. It is real life. And that is what people craved and are still craving. I could do that. And can do that. I can be real. And inspiring. And teach some strategy along the way. What you hear and see in real life.

In your opinion, were you a natural born entrepreneur or did you develop that aptitude later on? Can you explain what you mean?

I don’t feel like I was a natural-born entrepreneur mainly because it wasn’t something that I really knew was an option. I didn’t grow up seeing any examples of women in this role. I also came from a small town where the path was pretty much to go to college, get married, have kids. I honestly felt like I was behind because I didn’t get married until later in life. It didn’t even occur to me to do something different. I think that is one of the reasons I am so passionate about being an entrepreneur now. Because I want my girls (twins who are now 7) to truly believe they can do anything. And have some really amazing examples to look up to.

Was there somebody in your life who inspired or helped you to start your journey with your business? Can you share a story with us?

I would be remiss if I didn’t call out my husband Scott for his support. This year in the pandemic, when everyone else was slowing down and figuring out what Netflix show to watch for the week, I was heading down, creating, building, networking, recording the podcast, etc. I try hard to not work on weekends or late nights all the time, but a side hustle is a hustle. And he has been the glue that keeps everything together! I probably owe him a few 100 bedtime swaps (i.e. he gets bedtime duty with the twins 9 times out of 10). I won’t even try to pretend I can do everything.

I also worked closely with a business coach in a mastermind. I hired her to help me visualize where my business could go and without her insight and direction and the support of the mastermind community, I would never be where I am now.

It truly does take a village. And I hope to be that village for other women going forward.

What do you think makes your company stand out? Can you share a story?

There are three things I believe strongly in. Vision. Community. And Accountability. I will spend as much time as it takes with you teaching you how to craft your strategic vision as it really is the pillar that drives all things. So often we can be busy, but are we busy focusing on the right things? I also believe 110% in surrounding yourself with a supportive community. One that keeps you focused, challenges you, and encourages you when you need it. Being a solopreneur can be lonely, scary, and intimidating. You absolutely have to have that circle of trust. Finally, I would say accountability is my secret sauce. I have created strategies, systems, and sustainable processes to make sure that every single one of my clients has accountability from me. No matter if you purchased a planner, a course, joined a mastermind, or a 1:1 program. I even follow up on my free materials to see how I can help more. When you work with me, you kind of gets me for life. Relationships and customer experience will win every time in business.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  1. Self-Awareness. I know exactly what my strengths and weaknesses are and don’t try to be the expert at everything. I will lean on my community when I need help and am not afraid to admit that I don’t know everything. No one does. I truly believe people respect you more when you can share some vulnerability.
  2. Endurance. Let’s just call it what it is, but I hustle. I am also probably the most consistent person you will ever meet. I decided when I started this business that I am here for the long term. Consistency even when it feels hard, and awkward, and scary is when you grow the most.
  3. Creativity. As an Enneagram 3 I am a list person, but as a Pisces, I love to be creative. I could spend hours in Canva, come up with course ideas on the fly and create a new business model in my head at dinner. I love to create new things.

Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?

I had a mentor early on in my business that said just turn your brain off and send as many sales messages as you can. She was referring to selling on social media and inviting people to a product we were launching. It felt really icky. But I did it because I thought that was what we were supposed to do and what other successful entrepreneurs and coaches at the time were doing. It was a huge lesson learned in trusting your gut. Just because everyone else is doing it doesn’t mean you have to.

Which tips would you recommend to your colleagues in your industry to help them create a work culture in which employees thrive and do not “burn out” or get overwhelmed?

This is my favorite topic. And literally, the reason why I built my business. To stop the burnout cycle. And to take back control of your time with proven systems and structure to create a strategy that scales long term. There are two things I would recommend doing first.

  1. Do a time audit. Track your time, as in where you spend it with every activity over the next 3–4 days. It is so eye-opening to see where your actual time goes. And why you might be burning out in your current schedule.
  2. Try the CAKE method. I think of my day as a 3 layer cake. I mean who doesn’t want to chat about cake every morning. Each layer represents a priority. And there are only 3. Everything else is sprinkled. You can’t have sprinkles by themselves so you have to get to your cake first. It is so simple, but it really does help you dial in your focus without overwhelming it. My cake usually consists of one business activity, one family / self-care activity, and one 9–5 (my day job) activity. There is so much research on the power of 3 and I have found this is a really simple step to start with.

What would you advise other business leaders to do in order to build trust, credibility, and Authority in their industry?

I think the biggest piece of advice is to be yourself. There is no other you out there. You can do this by sharing the highs and lows of your business. So often we want to share the highs so we can build credibility and people, therefore, want to work with us but sometimes sharing behind the scenes, the lows, and even the struggles build even more trust and credibility. Take the filter off. Share your personality. People are craving that. And in the end, they will trust you more for it.

Can you help articulate why doing that is essential today?

I think there are very few working moms who are working their 9–5 and loving every minute of it. Not because they don’t love their job but because they have like 12 other jobs. I want to change that. . I want to show working moms, entrepreneurs, side-hustlers, etc. that there is a difference between time management and time freedom. You only get one life. So why not learn how to manage it in a way that gives you more freedom. Strategy. Productivity. Systems. They can all work for you allowing you to do more of what you love and focus on your VIPs. Very important priorities.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

I think the biggest mistake CEOs and Founders make is they have to “keep up with Jones”. Just because someone you admire has a new website doesn’t mean you need one. Just because they are running FB ads, doesn’t mean you should. Just because they hired a brand new team. That doesn’t mean you need to right away. Your business is yours. You have different goals. Different vision. etc. That means a different strategy. It is so important to spend the time figuring that out before focusing on what everyone else is doing.

Ok fantastic. Thank you for those excellent insights, Let’s now shift to the main focus of our interview about How to Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur. The journey of an entrepreneur is never easy, and is filled with challenges, failures, setbacks, as well as joys, thrills and celebrations. This might be intuitive, but I think it will be very useful to specifically articulate it. Can you describe to our readers why no matter how successful you are as an entrepreneur, you will always have fairly dramatic highs and lows? Particularly, can you help explain why this is different from someone with a “regular job”?

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. In my corporate career, there are more strict boundaries. In my company, that to-do list never ends.

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. I personally have the hardest time when I am not in a launch because it feels like I am not doing enough to scale. You have to balance that nurture season and launch season and the highs and lows that come with it. Ultimately building a business with passive income so the highs and lows are a little less intense is the goal.

Do you feel comfortable sharing a story from your own experience about how you felt unusually high and excited as a result of your business? We would love to hear it.

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. And go with what you believe. My entire focus of the launch and the program was completely different than any other course I had launched thus far because I was so passionate about it. I believe my mindset, passion, and excitement for the program are what have made it so successful. I am excited to see how it continues to grow.

Do you feel comfortable sharing a story from your own experience about how you felt unusually low, and vulnerable as a result of your business? We would love to hear it.

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.

In the end, the course was a failure (at that point in time), not because of the content but because it didn’t align with my priorities. I spent the entire Thanksgiving weekend stressing about how the launch was going instead of focusing on my family and being grateful for my clients.

Based on your experience can you tell us what you did to bounce back?

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.

Ok super. Here is the main question of our interview. What are your “Five Things You Need To Successfully Ride The Emotional Highs & Lows Of Being An Entrepreneur”? Please share a story or an example for each.

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? When the going gets tough, this is what keeps you going. It needs to be ironclad. I read mine every morning. It is the screensaver for my laptop. It is framed above my desk. Make it visible.

2. 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). What can you focus on right now that is going to move the needle forward? The rest is sprinkles and you can get to them when it makes sense. They are a bonus!

3. 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.

4. 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 have to slow down to map out your next steps to speed up.

5. 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.

We are living during challenging times and resilience is critical during times like these. How would you define resilience? What do you believe are the characteristics or traits of resilient people?

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.

In your opinion, do you tend to keep a positive attitude during difficult situations? What helps you to do so?

I am very much a glass-half-full type of person, but I will say when I start to feel anxious or nervous about the future or a difficult situation I lean into affirmations and journaling. I also am a big fan of taking a break from social media. As in full weeks or weekends. It is amazing how a little white space and some downtime can fix almost anything.

Can you help articulate why a leader’s positive attitude can have a positive impact both on their clients and their team? Please share a story or example if you can.

The majority of my clients work full-time or run a full-time business and are looking to grow and scale. Their biggest complaint is overwhelming (i.e. too many things on the to-do list) and burnout (i.e. they can’t keep going at their current pace). I feel like it is my job to show them that you can have success without either one of these. We focus each week on celebrating WOWs. Wins of the week. It helps keep in a positive perspective of how far each client has come in a short amount of time. So often we forget that each small step adds up to amazing progress. So setting the example of celebrating small wins and WOWs sets the tone for the following week and work ahead. It is a very positive practice. I highly recommend everyone try it to end the week on a positive note.

Ok. Super. We are nearly done. What is your favorite inspirational quote that motivates you to pursue greatness? Can you share a story about how it was relevant to you in your own life?

Measure the metrics that matter. I actually put this in my planner that I created this year because so often we feel like if we don’t have enough likes or follows or email subscribers that we are failing. But do those metrics really matter? It is a great quote to think about.

How can our readers further follow you online?

You can find me at hollymariehaynes.com

This was very inspiring. Thank you so much for the time you spent with this. We wish you continued success and good health!

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Holly Haynes: “Your why and vision should be so strong it literally holds you up when you fall”

by Ben Ari
Community//

Calvin Williams Jr. of FreemanCapital: “The fourth thing that is really critical to riding the highs and lows, is a longer horizon of success”

by Ben Ari
Community//

Jason Chan of Rakuten Super Logistics: “Know that everyone experiences highs and lows”

by Ben Ari
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.