Make Bold Decisions and Change Your Life

Tom Alaimo
The Startup
Published in
4 min readFeb 20, 2018

“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.

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About the Author

Tom Alaimo is a passionate B2B sales professional. He is currently the co-host of the TR Talk Podcast, where he and Ryan Warner interview leaders in their respective fields to learn how millennials can fast track their personal development. Tom is also an Account Executive at TechTarget and lives in San Francisco.

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Tom Alaimo
The Startup

Passionate B2B Sales Professional || Founder of Millennial Momentum || Obsessed with helping millennials develop personally || Gratitude, Growth & Grit