The Hardest Part of Being an Entrepreneur

I was recently featured on a live panel of female entrepreneurs who had left the corporate world to start their own online businesses. One of the questions that the organizer asked really struck a chord in me. What is the greatest challenge you’ve faced since starting your business, and how have you overcome it?

Since I left the corporate world to pursue the entrepreneur lifestyle full-time, I’ve faced my fair share of challenges with technology, time management, finances, lead generation, and digital marketing. But none of that seems to affect me - at least not in a major way. The biggest challenge that I’ve struggled with so far as an entrepreneur is the management of uncertainty.

You see, uncertainty is the natural way of life. Change is truly the only constant we can rely on, but yet we humans crave a sense of control and stability. This tension between wanting things to be one way and them naturally being another is the cause for most of our anxiety, stress, and suffering.

When you have your own business, uncertainty is something you need to become familiar with. You will never know with 100% certainty how something is going to turn out. You will never feel 100% ready to do something before you do it. You just have to try. And keep trying. And then try some more. You have to keep taking inspired action until eventually, you figure out something that works... and then take more inspired action to replicate it, scale it, and repeat.  

A few months ago, I was experiencing a lot of resistance in my business. I didn’t feel inspired or motivated to create anything new. I was resisting new clients and literally turning away 1:1 work. I didn’t feel like anything I did mattered and it seemed like my well of creation had tapped dry.

Looking back, I see now that this is a totally normal experience to have, especially in the creative space. You go through times of inspiration and creation, and you also go through times of introspection and reflection. You’ll have springs and summers, naturally followed by autumns and winters.

A friend recommended I watch an old Jim Rohn seminar during this time. In the seminar, Rohn speaks about managing your business in the “winter” seasons... or in other words, building your endurance to manage the uncertainty in your life. There will always be difficulty, but you must know how to face it. Even when things seem like they can’t get any worse - your heart is broken, you go bankrupt, your health fails, you lose a loved one - it’s up to you to use that time to become stronger, wiser, and better. It’s your responsibility to manage the winters by gaining more skills, more wisdom, more compassion, and more empathy to endure the hard times, and come through on the other side a more complete human being.

If you’ve heard my stuff before, you’ll know that I’ve dealt with depression and anxiety for a while. With that comes a regular surge of hormones and inconvenient mental fog that always seems to show up just when things are going really well in my life. So when my business started to take off and things were improving for me, it was no surprise that I got hit with a wave of depression and anxiety like never before. This caused me to feel even more uncertain and more unsafe in my business, because of the lack of certainty and direction that came with it. Instead of appreciating and loving the uncertainty, I became very fearful of it. I stopped taking action and I started retreating more and more into my darkness.

Thankfully, I have the tools and support team in place now to help me manage the winters so much easier. When I start to feel myself retreat into the space of uncertainty and discomfort, I recognize it and acknowledge that it’s OK to feel that way. It’s okay to not feel okay. It’s okay to feel any of your feelings. I simply acknowledge their presence, try to really sit with the emotion, and then let it go.

What can you learn from the winters? Hell, you can learn everything you need to know about yourself if you just pay attention. Notice how you react to difficulty. Notice how you react to uncertainty, obstacles, uncomfortable situations, people who trigger you, and moments you feel unsettled. What comes up for you? What thoughts arise? How do you speak to yourself? How do you treat others? What instincts naturally kick in?

These times of uncertainty are actually our greatest teachers. In moments when you are unsure of how to proceed or when you feel like you’re living so far below your potential, you can choose to see yourself with compassion and love, without judgment, and learn how you act when you feel unsafe. You can come back to a daily routine that helps you feel balanced. You can call upon your team of friends, mentors, coaches, and teachers to support you. You can seek out inspiration from others who have gone before you. Remember that there is truly no right or wrong way - we’re all just trying to piece it together and figure out which way to go next.

What matters most is how you treat yourself in these moments. What actions could you take to get you back to a neutral, baseline state? What do you need to have happen so that you can feel safe, supported and loved? What does it look like to put yourself and your wellbeing first? Who do you need to call upon in the process?

Not every day as an entrepreneur is going to be fun. There will be amazing highs and there will be significant lows - and that’s life. To try to resist and run away from the lows is to resist growth, expansion, and experiencing the fullness of being human. This isn’t supposed to be an unsafe, anxious struggle where you feel like a #hotmess 24/7. If that were the case, I’d recommend going back to the corporate world, where you can at least rely on having regular paychecks and benefits. But know that if you choose this lifestyle, there will be struggle. The hardest part of entrepreneurship is managing your relationship with uncertainty so that when these struggles do arise, you can figure out how to move through it a stronger, wiser, better human being than when you went in.

As Jim Rohn says, it’s not what happens to you that determines the quality of your life; it’s what you do that changes everything.

Keep your head up. Keep going. The winter will come and go. Spring is on its way.