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Stride Stories: In pursuit of the millennial dream

Stride Stories: In pursuit of the millennial dream

Today, in our first Stride community-member profile, we talk with Peter Giacalone. Peter grew up in San Diego, where his love for the ocean became a daily practice, as he lifeguarded every summer through college. Now, at age 25, Peter’s post-college story is the story of the Millennial generation – a generation whose quest to find fulfillment stems from autonomy and life-balance. Peter gave the corporate life a try, but eventually put faith in himself over the system, which led him to the freelance lifestyle. Today, Peter talks to us about the risk (and reward) of freelancing, how he keeps calm while surfing 15-foot waves, and the greatest health risk of his generation.

Stride: The job market has been rough for Millennials, what happened after you finished school?

Peter: I got a degree in finance because I liked math and it was real-world math to me. At the time, my cousin lived in Chicago and worked in finance. After graduating, I lined up an internship with him, but a few days before I started he told me he had lost his job. So, in turn, I had lost mine.

Stride: So what did you do?

Peter: No one in Chicago was hiring fresh college-grads with no experience. I tried so hard for three or four months to find a job, but eventually I came back to San Diego to try real estate, which is our family business. I got my license and hopped right into property management… but I found myself working a little too closely with my dad. I felt I needed to explore more, needed to see what else was out there. I wanted to create my own path, so I moved to San Francisco.

Stride: What happened in San Francisco?

Peter: In SF I worked for a health care consulting firm, my first salaried job with benefits. It was sold to me as this young company with the hip San Francisco vibe… very start-upy. I was an analyst, which mattered to me because I was working with numbers and money, which I had studied. Since the company was in the health care space, it was interesting; I could relate health care to growing up lifeguarding.

Stride: Was your family supportive of this move to San Francisco?

Peter: My dad would never admit this, but I think his plan was to keep the property management business in the family. My plan was to go explore, to see what I could do. But he was completely supportive of the move, and it was funny, after a couple months doing the salary thing in SF, the family business jumped out as something I really wanted to pursue.

Stride: So you quit the salaried, “sure thing” and forged off into freelance life? Were you scared?

Peter: I wasn’t scared because the “sure thing” wasn’t fulfilling for me. I sat behind a computer 8-9 hours a day. I was stuck on the phone, literally with a headset, calling a list of people (I would never see) to try and recover money. That was my job. Whenever there was something the company called an “accomplishment,” it didn’t feel like an accomplishment to me. I couldn’t stare at those two computer screens any longer. That was really the moment of truth.

Whenever there was something the company called an “accomplishment,” it didn’t feel like an accomplishment to me. I couldn’t stare at those two computer screens any longer.

Stride: OK, but isn’t it every Millennial’s dream to spend less time behind a computer? Do you actually spend less time working on a computer now?

Peter: With real estate, I’m out a lot. I’m networking, showing houses, seeing different houses, getting values on houses, reading the market. I’m very active, and I meet a lot of people. It’s definitely a social job. So, yes, I spend less time at a computer, and my time on the computer is more productive.

Stride: What was the worst part about moving from a salaried, employer-based life to an independent lifestyle?

Peter: Having no security. Real estate is all commission, it’s stressful. You make no money for awhile, which forces you to get up and get going. With a salary, you turn a little lazy – the money’s coming every two weeks, so you can put things off. Now, I can’t do that. I have to pay rent and feed myself. I’m in the trenches right now building my client base, so nothing is certain. I’ll be in this same spot for the next 6-12 months, but my advantage is I’m young, hungry and ambitious. I find that I work a lot more now that I’m on my own – I just canceled a surf trip to Mexico this weekend because I need to work.

Stride: What’s the best part about working independently?

Peter: Making my own schedule. Not doing the 8-5, not clocking in and out. I’m more productive when I set my own schedule. And I set aside an hour for what I want to do – go for a run, go surfing, whatever. I’m my own boss now, which is liberating. But there’s a risk in that – I can get lazy and no one will be huffing-and-puffing down my back, telling me to work. But you have to look beyond that and put faith in yourself.

I’m my own boss now, which is liberating. But there’s a risk in that – I can get lazy and no one will be huffing-and-puffing down my back, telling me to work.

Stride: Did you have any idea how to buy health insurance when you started working freelance?

Peter: I didn’t know the first thing [laughs]. I had been on my parent’s plan forever, and Stride’s customer service helped me out big time. I had some billing issues which you helped straighten out… I wouldn’t have been able to get the health care I wanted without Stride’s help, and that’s just being honest.

Stride: So you grew up lifeguarding and have led an ocean-based lifestyle, mostly through surfing. What do you get out of your relationship with the ocean?

Peter: Well, there are no cell phones in the ocean, so you’re actually able to think out there. Being in the ocean is tranquil, it’s soothing and therapeutic, and I get exercise without even knowing it. There’s nothing quite like the ocean… nothing as powerful, nothing as big. It’s massive, so there’s always something new to discover. Even 15 miles from a major city like San Francisco, there’s a secluded beach to be found.

Stride: You surf big waves. How big are the biggest waves and how do you stay calm out there when it’s huge?

Peter: First, you have to know your limits or you’ll definitely get hurt. The biggest days are about 15 feet. My strategy when things get that big is to go back to my basic instincts. I remind myself that I’ve been in the ocean countless times before, but other than that, it’s all instinct. When I fall on a big wave, I don’t even have time to think – I click my mind into a calm state and kind of pray that I find the surface soon. It’s hard to say what my longest hold down has been, because every second underwater feels like 10 seconds. But it was probably a day out at Ocean Beach (San Francisco) where I was under for about 30 seconds… which felt like a lifetime [laughs].

Stride: What is the greatest health risk for your generation?

Peter: Addiction to our phones [answers without pause]. These phones are something humans have never seen before and were only recently introduced, and look at how addicted we’ve become. Going forward, humanity’s issues are going to be texting while driving, or everyone’s eyes failing from staring at a screen too long. It’s a risk we don’t know much about and don’t talk much about, but technology is a real risk.

I recently deleted Instagram, Facebook and Snapchat because I realized how much time I was spending on them. When nothing was going on, those were the three apps I found myself looking at. One day I thought jeez, I could be doing so many other things besides staring at these 10-second clips from Snapchat. I couldn’t do it anymore. Now my iPhone is just a little black brick – it’s for texting, calling and business only – and I’m okay with that.

One day I thought jeez, I could be doing so many other things besides staring at these 10-second clips from Snapchat.

Stride: So you just went cold turkey? You didn’t find yourself wanting to reinstall those apps?

Peter: The first couple of days I thought about it (those apps), but then my attention went somewhere else. It’s been really nice, I get to put all those wasted minutes into something productive. The tech-purge… it’s good, I highly recommend it [laughs].

Stride: Where did you find yourself having more time?

Peter: I have more time to work, which I need! And I take more mini surf breaks.

Stride: Alright Peter, thank you for the call. Keep the good momentum going in San Diego.

Peter: Thanks a lot.

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