“Freedom lies in being bold.” ― Robert Frost

As I reflect on where I am today and the strides I’ve made in the past few years both professionally and personally, I see one trait that links everything together: making bold decisions.

Below are a few stories that I talked about in my recent podcast and why making bold decisions can help fast-track your personal development.

1). Introduction To Sales

In college, I played tennis competitively and, naturally, taught tennis every summer. When I got shoulder surgery and was unable to teach, I needed to find an alternative. I stumbled upon an advertisement for a Sales job at Cutco. For those unfamiliar, this means cold calling people to set appointments to sell them kitchen cutlery in their homes.

So I was a 19-year-old kid (who looked 13), with a sling on one arm and a bag of knives in another, walking into people’s homes to sell them on the dream of Cutco knives. That summer, I was the number 7 rep in all of New England and made some good money.

And that’s when I fell in love with Sales. And my life hasn’t been the same.

2). Joining The Professional Market

The next summer I interned at TechTarget, where I currently work. I loved the atmosphere of the company and told the Recruiting Manager (who ran our intern program) that I wanted a job. She said she appreciated the interest but that I hadn’t done enough over the summer to earn a position. The job was in Sales and I did no networking or showed any passion for the craft of Sales.

The next day, I knocked on the CEO’s door unannounced. In an intimidating manner, he says “Okay, you got 5 minutes. What do you want?”. Long story short, we talked for 55 minutes and I got the job.

This opened my door to the professional world, which changed my life.

3). Moving Across The Country

While working in Boston, I knew my next growth opportunity would be to move to our San Francisco office. One night, I heard a tip that someone had quit in that office. I immediately called the Sales VP that ran their office — we had never spoken before. I said “Bill, this is Tom Alaimo, I know there’s an opportunity out there and I want it.”

5 days later I signed the papers and moved across the country. Best (bold) decision I’ve ever made.

4). Creating Content

In 2017, I wanted to make my voice heard. I wanted to build a mastermind network. I wanted to write and to create a podcast but the fear of letting my colleagues and strangers know my thoughts were seemingly too big of fears to conquer.

Then one day, I finally hit “submit” on my first blog post. The next week, I hit “submit” on my first podcast. It’s completely changed my life.

I wrote about all of the lessons I’ve learned and this has been an amazing experience.

My Challenge To You

Identify where you have an opportunity to make a bold decision that can impact your future and GO FOR IT.

Ask for that raise, join that non-profit, take on that fitness challenge.

Nothing worthwhile in life will come easy.

Climb that mountain and get after it.

Originally published at medium.com


  • Tom Alaimo is a obsessed with helping others reach their full potential. He works in B2B sales and runs Millennial Momentum, a blog & podcast focused on millennial personal devleopment. When not writing or podcasting, you can find Tom playing tennis, running endurance races or reading a good book in San Francisco. For more info, check out millennialmomentum.net