5 Key Tips to Successfully Ride the Rollercoaster of Being an Entrepreneur


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The life of an entrepreneur can be a rollercoaster. After closing my first 7-figure business during the 2007–2008 Global Financial Crisis, I made sure that my future businesses were resilient. As much as this “crash” was a crisis, it was also the opportunity to create the life I really wanted. I had let my business take over for my needs. I am thankful for the lessons learned, and I use that experience not only in my own businesses but also as a business mentor when I am helping clients create resilient businesses that support their needs and desires.

To be successful, you need grit, passion and faith in the value of what you are doing. People think that going into business will give them the freedom to do whatever they want, but if you’re not careful, the business can take over your life. There is always a lot of testing and measuring, and not everything turns to gold straight away. Consistent and persistent action to keep going, even when things haven’t gone to plan, is needed.

Being persistent is different from just working hard. Take time to get clear, get in alignment and follow the path from a place of clarity. When things don’t go to plan, you need to be agile and open to change to suit the current operating environment. Celebrate the highs, and enjoy the journey — that is the sweet spot, even more than the end goal. In all my businesses, I align to follow the joy. When you enjoy what you do every day and are bringing value to others, that is when you are living the dream! Here are five key tips to successfully ride the rollercoaster of being an entrepreneur:

Related: What I’ve Learned in 20 Years of Being an Entrepreneur

1. Good foundations

This is systems and structures, but more importantly, this includes knowing how to support yourself, building a good support team around you and utilizing them by asking for help when you need it.

This was a big lesson for me in my first business. The African proverb, “If you want to go fast, go alone. If you want to go far, go together” comes to mind. You might be able to do all of the things in your business, but if you want to scale, you need to bring in team members. In order to bring in a team, you need systems and procedures. I remember returning from a business trip when I was about 6 months pregnant, and I was chatting with the person sitting next to me on the flight. We were talking about my travel business and how I would manage once I had the baby. She encouraged me to read The E-Myth by Michael E. Gerber, which emphasizes that if you want a successful business, rather than just creating a job, you need the business to work without you. If you want to grow and scale, just like any building, you need strong foundations.

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2. Emotional intelligence

Emotional intelligence is being able to be an observer of your emotions and understand why you might be experiencing them, and use them to guide you to what you need to do next. Knowing how to support your own emotional needs is one of the keys to a happy life.

People think that “business” and “personal’ are separate aspects of our career paths, and yes, sometimes they are — but a “light-bulb” moment for me was realizing that this is never entirely true. Everything is personal because we are human beings. It was a big shake-up during my business closure (I was also going through a divorce at the time). I realized that there is strength within vulnerability. It’s okay to admit that you are not okay, and it’s okay to ask for help. It’s also okay to say “I need time away” or to say “no” to things that drain your energy. The realization was that I needed to trust myself and let go of fears around emotions, make decisions with an open heart, be guided by my intuition and prioritize my own needs.

Related: Entrepreneurship Is All About Overcoming Obstacles

3. Empathy

Empathy is being able to consider someone else’s perspective, how they are feeling and why they may be acting a certain way. Understanding this will be a great tool for you in resolving issues and in any negotiations.

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Developing a greater understanding of the role empathy plays in your working life will help with managing teams and growing your business. As a negotiating tool, I always look for what’s in it for the other side as well as how and why they may have formed their point of view. It will help you determine what their expectations are and help you curate an offer that will be acceptable. It helps to establish long-term mutually beneficial relationships. It’s not always about an immediate win or two opposing sides. It can be how you work through challenges and support each other in a common goal.

Here’s an example from one of my own businesses, The Bubbles Review, which publishes articles and creates events and tours on and sparkling wine. When we went into lockdown for the pandemic, the events and sparkling wine industries were severely affected. Restaurants were closed, and wineries needed to close their cellar doors. I had to postpone our series of The Bubbles Festivals indefinitely. Understanding how difficult this was, I wanted to do something to help.

We host a section on our website where we feature reviews on Sparkling Cellar Doors, so I decided to create a Virtual Sparkling Cellar Doors listing to feature wineries and wine importers who had suddenly lost their usual distribution channels. I made it free for them to participate because it was more about giving back and helping. We promoted it to our database and social media, and I showcased virtual tastings, interviewed some of the winemakers and shared them on our page. The relationships that were formed during this time have been long-lasting. When it was time to invite wineries and wine importers to be exhibitors for our events in 2021, it was an easy “yes” for them to sign up, as we had already negotiated to a point of trust in our shared goal of promoting these lovely sparkling wines to our audience.

4. Manage your energy

One of the most important resources is your own energy. Knowing how to read your own energy, and that of others is crucial. Failure to do so will lead to burnout. If you are experiencing resistance, reset and restore your energy until you can move forward from a place of inspiration.

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I didn’t always get this right, and once I had reached burnout, it was very hard to restore my energy from there. In some cases, it can take years. I now protect my energy daily. I listen to my body. I schedule regular wellness activities and take time out when I need to. I choose what and who I spend time with based on what brings me joy. I don’t take on projects or clients that do not align with who I am or what I want to do.

Related: Welcome to the Entrepreneur Roller Coaster. Here’s How to Ride It Forever

5. Know your value

This can be achieved by aligning to your value set and operating from there. When you operate from a place of value, you eliminate self-doubt and align with your sense of purpose — and you’re less likely to be affected by any negativity.

Aligning with your values is also a useful way to restore energy. In my first business, it was a big transition from simply managing myself to needing to motivate my entire team. This topic is now one of the most popular workshops that I deliver for small and large organizations, as it allows you to create a company culture that all of your staff will engage with. You will find all of your team on the same page instead of top-down instructing, and you will have all of your staff working as a team to achieve your shared goals.

Customers will align with businesses that have similar values to them. For you, personally, when you are working on things and working with people who align with your values, this is when it feels like you are following your joy. Our businesses should work for us, not the other way around. My biggest takeaway is to not put off living your dream life and wait for something to happen in the future. It really is about enjoying each of the steps along the way. When the business becomes stressful, remind yourself that business and life are supposed to be fun.



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