Dealing with the emotional side of being an entrepreneur


Teja Chekuri, global entrepreneur. Founder and director of Ironhill Brewery.

There’s a lot of discussion about the glamor of a startup and entrepreneurship in general, but little about the emotional toll it takes on you. It requires gigantic reserves of mental stability and faith, which can push you into a deep spiral of self-doubt that results in hasty decisions. Most of this is undocumented and unrecognized by the entrepreneurial ecosystem.

While people will tell you that being an entrepreneur is a blast, let me introduce you to the dark side (and how to fight the monsters):


Mental health

If you’re worried about debts, salaries and payments, as well as plans for the future, success parameters and financing, it’s safe to say you have a lot on your mind – and it won’t go away anytime soon. I used to think it would get better if I hit a certain profit number. To my surprise not. It just adds more to the pile of worries that come to mind that sometimes overlap with your personal and professional life, which can create an emotional mess.

While the stack gets higher, you should get better at it over time. The mind is a muscle that can be trained, so focus on training it to handle things better. Find your own method for the madness around you. I found my organization wizard in my own handwritten to-do list for the entire week. There was something therapeutic about writing it down and scratching it off that gave me a sense of accomplishment against an endless list.

Consider hiring several experts who can coach your mind through this phase and lead you to the next.

Family and friends

This set is often the first unfortunate casualty of the life you chose as your business swallows you up. You spend hours on your business hoping that when you’re done, you can sit back, relax, and enjoy time with them. However, “Done” is a shifting goal post, and by the time you realize it, it’s too late. Without the support of colleagues in the office, this life can get very lonely and can take a huge toll on your sense of belonging – getting hard into the reason for the life you’ve chosen.

Your home team is important. Very early in my journey, as I was drowning in work and taking on more, a mentor pulled me back and encouraged me to reconnect with my family. Even though I did so reluctantly, they helped me reconnect with love and joy. Today they are my biggest cheerleaders and confidants. Take a day off to spend time with your family. It will reaffirm your priorities and the reason you chose this life.

Financial health

This will get thrown out at least once or twice a year, even if you are super careful and smart. Startups have a way of sneaking chaos onto the balance sheet. There will be times when you want to shut everything down and keep what little money you have. Other times you want to risk it all. Your CFO will have a hard time getting things under control. Lots of money or no money can be an emotional rollercoaster, but a good business requires you to rise above it. However, that is difficult when you see the moolah roll in or disappear.

Separate your personal and professional assets. The smartest thing I did was hire a very strong CFO who rules the money with an iron fist and can stand up to me. I have the option of brushing them aside as the owner of the company, but as a rule I give in unless I can convince the CFO of the rationale for the expenses. It has helped me save the health of my financial positions and the profitability of every business I run.

Physical health

This life will cheat your physical health. I have often seen entrepreneurs over or under exercising their health. Poor health can also contribute to your insecurities, giving you another punch in your pocket of emotions and making you perceive negative thoughts where there are none.

Health is the real wealth. If you are healthy, you can do your business. A sick CEO can inspire less confidence in investors, customers and teams that work with them. I decided to pick one activity that works for me and to get a coach, and it’s the best thing I’ve done for myself.

Existential Anxiety

This is a recurring nightmare that is a bane in every entrepreneur’s life. The frequency should decrease as your business moves towards success. Nowadays I have reduced this to once a year. You will question everything you do and imagine a different life or a more familiar path that your group mates would have taken, leading to a more traditional lifestyle. While everyone chose to live a simple life, you chose to seek out and fight the monster.

There are two ways to combat this nightmare. Surround yourself with successful entrepreneurs first. Create a circle of trust. Contact them to chat to reconfirm your choices in life. Second, give back to other entrepreneurs around you. Help, mentor or share advice on success. Through them you can reaffirm your beliefs. I’ve taken the dual approach and it works every time the nightmare reoccurs.

Success parameters

Am I successful? This is a question that will haunt you regularly. It can be frustrating and drag you down bit by bit if you don’t define your own success parameters.

Create your own little reasons to celebrate milestones – then celebrate them. I’ve set internal benchmarks that we celebrate when they’re achieved. When we started doing this consistently, it reassured me that we were on the right track. That’s a healthy feeling that I’ll hold onto until we hit the next milestone.


Don’t be afraid of the monster. You will meet many of them, and they will take various forms. The thrill of entrepreneurship lies in overcoming your fear of facing the monster and knowing that you are willing to win. Business Council is the leading growth and networking organization for entrepreneurs and leaders. Am I eligible?