Taking Little Bets to Achieve Big Results

Taking Little Bets to Achieve Big Results

I consider myself a risk-averse person, especially compared to my thrill-seeking boyfriend who jumps out of planes and skydives for fun. But that doesn’t mean I’m opposed to new opportunities. If we didn’t take risks everyday, we literally wouldn’t get anywhere!

I’ll be the first to confess that unknown situations give me anxiety, but using logic over emotions helps to push me out of my comfort zone… in a healthy way. The best way to describe how I tackle new challenges is illustrated by Peter Sim’s book Little Bets: How Breakthrough Ideas Emerge from Small Discoveries. In short…

“Little bets are concrete actions taken to discover, test, and develop ideas that are achievable and affordable.”

I discovered this book after quitting my full-time catering job to start a corporate training business on millennial engagement in the workplace. My first mission was to read all the business books I could find, and this one stood out from the rest.


Getnugget.co provides an excellent summary, including three main points of the book:

  1. Utilize little bets to develop new ideas, then bet big to capitalize on successful ideas.
  2. Adopt a growth mindset. Redefine problems and failures as learning opportunities.
  3. Gain inspiration for new experiments through play and improvisation. Have fun.

On a personal level, it was neat to read this book because taking little bets is how I discovered wanting to pursue a career in events instead of dentistry. Ironically, I didn’t follow this methodology when trying to start my corporate training business, but hey – success isn’t a straight upward trajectory.


When I went off to college, I wanted to be a dentist. My dad and uncle are successful dentists, and their passion was infectious to me and my two brothers. Needless to say, none of us ended up as dentists, but how could I have known that at the time? Thinking this path was my destiny, I got involved with the Pre-Dental Society at UC San Diego.

To this day, I’m grateful this “little bet” of assisting in our non-profit dental clinics, volunteering aboard a navy hospital ship, and becoming certified to take mouth x-rays. All those experiences were rewarding, despite realizing my true passion for hospitality and events.

I’d been producing events since high school, starting with our annual “Pi (π) Day” event and leading into a Masquerade Ball and District Convention in college. At the time, I thought event planning was just a hobby, not a career. These “little bets” had paid off, experimenting through volunteer work and gaining hands-on experience in a field I was interested in.

Generally, people fear change, failure, and wasting time, but we can choose to look at those situations differently. I mean, if I saw each failed romantic relationship as a waste of time, I’d be way too depressed to try again. Fortunately, even if my “little bets” don’t pay off, I can still learn from them, and that makes failures worthwhile.


Even Peter Sims mentions the normalcy of mistakes in his book:

Ingenious ideas almost never spring into people’s minds fully formed; they emerge through a rigorous experimental discovery process.”

Unfortunately I didn’t take this advice when it came to starting my corporate training business.  I was so hesitant to rebrand myself and didn’t understand the connection between being an entrepreneur and making little bets. Instead, I planned and researched for a whole year and didn’t execute anything.

Part of my discovery process was both accepting that I didn’t have a passion for millennial engagement as a living and rekindling my excitement for events. Each time I met someone who wanted my advice on getting into that field, I expressed how much I missed the thrill of planning and being onsite.

Honestly I think I was lucky to have a supportive group of peers that gave me feedback on my career path along the way. Things could have changed sooner had I been more purposeful about taking little bets. I don’t regret everything I learned about starting my own business, but it wasn’t enjoyable for me.

While I still won’t jump out of planes for fun, it’s neat to walk into unknown situations nowadays with more purpose. Identifying little bets in any anxiety-inducing scenario and reminding myself of the “why” behind them helps me accept failure as a part of the learning process and makes life that much more rewarding.

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