5 Ways to Break the "Entrepreneurial Insanity Cycle" in 2018

There's the old adage that the definition of insanity is doing the same thing over and over again and expecting different results. If this were true, I think that every entrepreneur could at one point call him- or herself insane.

Recently a colleague asked me, "What frustrates you the most as an entrepreneur?" I replied, "That I have spent the past 10+ years of my life as a consultant to small businesses helping them to avoid common start-up pitfalls and to not spend money where they don't need to, yet I often don't seem to follow my own instincts. "

It could be described as an out of body experience. In my almost three-year-long journey building Gugu Guru, each year's end I have the same routine: I look at my books and the activities of the past year and say to myself, "This upcoming year will be a fresh start, I will not make the same mistakes twice. I will learn from what works and what doesn't work and be smarter. This year will be different."

Yet, inevitably, at the subsequent year's end, the year that was supposed to be the year I made fewer and different mistakes, I find myself in the same position. Granted they're not the exact same mistakes, so perhaps this behavior doesn't qualify me as insane but it has definitely made me question my sanity nonetheless.

So this year I am resolving to put an end to what I am calling the "entrepreneurial insanity cycle" once and for all. I'm not naive to think I won't continue to make mistakes this upcoming year, but hopefully the mistakes will be different and I will have the proper controls in place to truly learn from them.

I've mapped out five tenets that I plan to follow to the letter this year. Here they are:

1. Know my strengths. Almost directly after launching Gugu Guru, my dad (a CPA and numbers guy) told me that I had to hire someone to help me with my operations and finances. Each time he offered this sage advice, I would poo-poo it saying I could do it all myself. Mostly because, as the founder of a bootstrapping and almost completely self-financed company, I am constantly weighing what I should be hiring someone to do versus saving the money and doing myself. Finally, I realized that I really can't do it all. I recently brought on a career COO/CFO and self-professed "process geek" as a consultant. The first work sessions were definitely eye-opening and perhaps a bit ego-bruising, but ultimately empowering. What's more is that having someone put a framework down allows me the headspace and time to focus on the things that I am good at -- putting me in a better position for success in the next year.
2. Know the numbers. To avoid making the same mistakes you have to know your numbers and I mean REALLY know your numbers. It doesn't just mean keeping generally on top of your expenses and income, it means knowing your COGS, your CAC, your break-even number and your profitability targets. It means knowing these numbers, living them and owning them all the time, including the good, the bad and everything in between.
3. Trust my gut. I cannot tell you how many times that before I moved ahead with something, I questioned whether I really need to do that very thing at that very moment and my gut screamed, "no!" Yet, I ignored my gut and proceeded. Fast forward to when I recognize that the endeavor was in fact a waste of resources and wonder why I didn't trust my gut. The reason being I often go into things feeling so strongly that they're good ideas at the start that when my gut starts telling me otherwise, the self-doubt creeps in: do I trust the instincts of Monica today or the instincts of Monica a week ago when this idea came around? Spoiler alert: In 2018, I plan to always go with the instincts of Monica today.
4. Reflect on activities at least once a month. I am resolved to sit down at least once every calendar month, if not more frequently, and reflect on what's working and what's not working. On this same note, I am also resolved to not beat myself up if something is not working, but instead to figure out if there's a way to correct course and make it work or alternatively recognize that it's time to stop the bleeding and put the idea to pasture.
5. Establish an ongoing open and honest dialogue. This goes for all stakeholders, i.e., my team and also my customers & prospects. In 2018, I want to foster an environment that uses radical candor. While we do some of this now, there's the opportunity to do more - whether it's conducting ongoing surveys, emailing with Gugu Guru's users personally, continuing to grow our customer advisory board or performing frequent usability testing. One thing is for sure: I am much less likely to make the same or similar mistakes if I am always soliciting feedback and listening.