Comfort vs. Risk: Here’s What It’s Like to Choose Between a Dream Job and Entrepreneurship

Getting a job that pays comfortably in this day and age is tough, so when you not only have a job but also have it at arguably the most valuable company in the world, most people see it as a dream come true. This was the position Michael Peggs found himself in for the last couple of years while working at Google.

Michael’s resume was unparalleled. He graduated from Babson College, a prestigious business school in Boston, Massachusetts. After a brief stint on Wall Street, he found himself in Silicon Valley working for a startup; Google came calling shortly after.

Google offered Michael everything jobseekers dream of: prestige, money, perks and a great work environment. Over the next four and a half years, Michael enjoyed every minute of it, but he simply believed he was meant to achieve more. His last day at Google was on October 3, and here, he explains to us his experience of leaving comfort for uncertainty.

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Tell us a little bit about your background before you joined Google.

“Like a lot of people, I wanted to be an investment banker before I even knew what that was, so I went to an all-business undergraduate college by the name of Babson College in Boston, Massachusetts, the world’s number one entrepreneurship school. I majored in entrepreneurship and finance with the goal of going to Wall Street. I ended up interning at Wall Street for many years beginning my freshman year. So from age 18 all throughout college I interned on Wall Street at the same bank and had the realization very early on that it’s not what I wanted to do. Like for a lot of people, society and parents and pressure told me to stay. I decided to quit that job, move to the West Coast to find myself and found my way to a small startup. I felt in some weird way that I had conquered the East Coast in banking, so let me go to the West Coast and conquer Silicon Valley. It didn’t quite end up that way; I didn’t really enjoy my startup experience, but then Google came calling and I was there for four and a half years as of last Friday on October 3. I kind of said my goodbye to Google.“

How useful has your college degree been for you?

“I think Babson provided a great education. We had this freshman year class and the name has since changed, but back then it was called ‘Foundation Management Experience,’ or FME, but you essentially start a business your freshman year. You take the first semester to plan it and the second semester to run it. I was one of the CEOs of my business and it was an amazing experience. When it came time for interviews for internships, it really helped to set me apart to say that I was the CEO of a business at age 18.

Was Google the first job you really enjoyed?

“I would say I enjoyed it for the right reasons. Banking, for example, I loved it. I loved the prestige. I loved the money and the status in my younger years when I thought that stuff mattered for all the wrong reasons. Google was the first job that [put me] particularly in a professional context where I was surrounded by people that were smarter than me. I was challenged and it was fun. Google had these commandments, one of them being you don’t have to wear a suit and tie in order to come and get work done and it was a culture in which I responded to. So yes, Google was the first job that I thoroughly enjoyed for the right reasons and continue to enjoy four and a half years later, which is one of the reasons I stayed so long when most people would leave a lot sooner.”

What are some important lessons you learned from Google that you’ve applied to your new business?

“The number one lesson I got with Google is that no one knows the answer. You have a company, 50,000-people strong, number one company in the world, the smartest people in the world — most people don’t know that Google has the benefit of corralling resources and people into one room and taking the time to figure it out, but even we don’t know. I think there’s comfort in that. There’s comfort in knowing that there is no right or wrong and so you try. The result comes through trial or triumph but I think too often, particularly people who have these entrepreneurial dreams, we don’t take that leap of faith because we feel like we’ll fail or we’ll make a mistake, but technically there is no such thing as failure when there is no right answer. No one has the answer so you might as well try your best to figure it out anyway.”

Most people leave companies to be a part of a startup that has some major clout already, whether it’s great funding or the team involved. It seems that you’re starting from scratch with your new business. What is that like?

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“… I believe in the art of the side hustle. So for two years I’ve been working nights and weekends using my Google paycheck to fund my business, and before that I was kind of in the planning and brainstorming iteration phase for a years, so this has been three years in the making. Am I still bootstrapping it? A hundred percent. I have a business and I have funds saved up and I’m building this thing myself from scratch. I think sometimes people think they have to go from 0 to 100 but that’s not the case, right? I think many entrepreneurs, particularly those who don’t come from financially stable backgrounds, whatever that means relative to your position, need to take baby steps.

What was going through your mind when you were deciding whether or not to quit Google?

“Well just two things relative to Google. What I realized is that Google is as good as it gets. The only thing better for me was doing it for myself. So at 24 I joined Google, and that’s pretty young to hit the peak of corporate careers in the sense that no company in my view is better — the only thing better is doing it for yourself. That said, I think it took, as I mentioned, three years to build the confidence to take that leap of faith, and what I learned is that we all act when our faith is more than our fear. In those three years, I spent a lot of time building faith in myself, saving enough money, having proof of concept, getting my first client, blogging and being recognized for my written word. That built my confidence in myself and when that tipped away from fear, that’s when I went to my manager and said, ‘You know what? I think this is it.’ “

How did your boss respond when you broke the news?

“Google is not like most companies, so this will sound odd, but I was fully transparent. I believe in an open-door policy and I believe in candid honesty, so I told my manager, ‘This is the long term goal and it would be great if you could help me get there. Let’s rock out together.’ I was fully transparent and that spoke to him. That speaks to Google and the culture that they created and just kind of my nature of just being brutally honest sometimes to a fault.”

Based on your experience, what do you think is harder: breaking up with a long-term girlfriend or breaking up with a job that you are comfortable with?

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“That’s deep. I mean, honestly, I think they’re very similar, right? You’re emotionally attached to both. Oftentimes, you romanticized the past looking back, although you know the right thing to do in retrospect. If I have to give you an answer and the answer is binary, I would almost say breaking up with a company is more finite. In this day and age of our hookup culture we tend to slide back and play often — that’s just human nature. It would be much easier to do that personally than professionally. So I would say breaking up with a company is harder in that it’s more permanent. But I think both are very, very similar.”

What advice would you give someone that has a great job that pays well, but deep down they know it’s not what they’re meant to do?

“I recognize the familiarity in that circumstance because it was mine. I would tell them to ask themselves three questions: The first being ‘What is your story?’, the second being ‘What is your gift?’, and the third being ‘How can you serve as many people as possible?

I believe that we all have a story, right? It’s our job to tell that story, to market that story and sell that story — that’s the essence of personal branding for me, but you need to know thyself. What do you do better than anyone else? Then to bring that to the world and affect as many people as possible with your service.”

Tell us a little bit about what you are working on next.

“So my full-time interest right now is my blog MichaelPeggs where I offer online courses regarding career and personal branding. I’m working on a web design and development firm that focuses on manifesting your brand and online presence — that can be through a social network or it can be through your personal website or blog. So I’m going to start helping people design and develop their personal websites and blog as an extension of their personal brand.”

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