With the new year, I’m kicking off a series of Career Q&As with successful leaders. The goal is to provide insightful lessons and practical advice you can leverage to further your career. The first one is with Dan Jimenez, who I first met in business school. There are a lot of gems in the interview. I particularly love his advice on career risk, how to think about the different decades of your life, and how he bounced back from an early career setback. Enjoy!

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Dan Jimenez is the Chief Operating Officer of Chatbooks, a company that creates photo books right from your phone. Since joining Chatbooks in early 2015, Dan has helped the D2C business scale revenue 30x while growing the team to over 130 and fulfilling orders to 45 countries worldwide. Prior to his current role as COO, Dan led the raise of $25M+ of venture financing as Chatbooks’ CFO. Previously, he was an associate at Peterson Partners, a Utah-based Private Equity & Venture Capital fund, as well as a strategy consultant at Accenture. Prior to earning an MBA at the BYU Marriott School, Dan was a vehicle dynamics engineer at Ford Racing where he was part of winning two NASCAR championships and 33 race wins, including the 2012 Daytona 500. Dan is a frequent guest lecturer at universities on topics of entrepreneurship and strategy. You can find him on Twitter at @TheDanJimenez.

1) What’s a book that has influenced your career or life, and why?

Zero to One by Peter Thiel. I happened to be reading it at the time I was faced with the decision of either sticking with going into strategy consulting after completing my MBA, or instead take a risk and join Chatbooks, a tiny Utah-based consumer tech startup. There’s a segment of the book where Peter describes in painful detail how an MBA teaches many otherwise smart and talented individuals to become risk-averse optionality-seekers — and that choosing the consulting path was the ultimate move of optimizing for career optionality that an MBA grad could make. I knew at that moment that I had to take risks early in my career if I wanted to accomplish something special. I knew that every year I waited to take that career risk, it would make it less and less likely that it would ever happen. Zero to One has been a book I’ve read and reread, as it has principles that I think apply well beyond business into life.

Was there an experience you had before age 21 that shaped who you are? What was it?

When I was 21 I worked my first internship as a mechanical engineer at a small NASCAR racing team in North Carolina. I was young, inexperienced, and very intimidated by the very smart and talented professionals around me. I didn’t grow up “wrenching” on race cars, I was an engineering and design nerd who thought race cars were cool. But I felt like the ultimate imposter, to the point I went into work each day sick to my stomach that I’d do something embarrassing. That summer taught me the importance of portraying confidence and not being afraid to ask questions when you don’t know the answers. I figured out what I could uniquely contribute to the team and focused on providing value where I could, and ignored what I didn’t know yet.

How has a failure, or apparent failure, set you up for later success? Do you have a “favorite failure” of yours?

I worked the last 18 months of my undergrad program as an engineer at an oil & gas services business. I enjoyed the job and liked the people I worked with and hoped it would be a place I could spend the first phase of my career. I assumed things were going well enough that a full-time offer after graduation was a lock. A few weeks before graduation I found out I wouldn’t be getting the offer to join full-time. I had apparently done and said some things that rubbed my boss the wrong way. I was in a state of disbelief, but with graduation a few weeks away (and now without a job) I didn’t have time to sulk. I walked out of that office with a chip on my shoulder that I’d prove to them that they were wrong about me. I’d become a kick-ass engineer and grow well beyond what that company could have ever provided for me. I know it sounds quite egotistical, but that experience has been a constant motivator for me to work hard and prove that old boss wrong 🙂

What advice would you give to a smart, driven college student about to enter the “real world”? What advice should they ignore?

One of the best pieces of career advice I ever received was from a Managing Director at Accenture during my MBA internship. He said (paraphrasing) “In your 20’s get as many diverse experiences as you can. In your 30’s specialize. In your 40’s make your money. And in your 50’s start to give back and mentor others. If your focus is right in your 20s and 30s, then you’ll make all the money you need to in your 40s and after”. I liked this because it put into perspective how long careers are and that you need to approach it in phases. It’s also helped me to not worry about money so much in my 20s and 30s. Optimize for the right experiences right now, and the money will take care of itself later.

What are the bad recommendations you hear in your profession or area of expertise?

I think there can be too much emphasis put on “do what you love and you’ll never work a day in your life”. I got the chance to work in my “dream job”, as a vehicle dynamics engineer for a professional auto racing team. After the honeymoon period wore off, it kind of started to suck. It was a hard job, and “success” was dependant on so many variables outside of my control. The sport I used to love had become the job I was growing to dislike. Compare that to what I do now, operating a consumer tech company that helps consumers get photos off their phone and into their home. I wouldn’t say I’m naturally passionate about printing photos. But I do greatly enjoy the challenges of operating a business. The substance of the product or service at Chatbooks could (and will) change, and I’d still be just as happy because being an “operator” is at the core of what I enjoy doing. 

If you could go back in time to when you were entering the workforce and give yourself one piece of advice, what would it be?

Ask more questions. Don’t be afraid of what you don’t know.

What’s one of your proudest professional accomplishments? (while this can include an obvious accomplishment, feel free to include a more personal one)

Growing Chatbooks into a business that serves millions of happy customers, employs 130+ extremely talented professionals with a culture that makes it a joy to come into work. 

Since entering the workforce, how have you changed or transformed?

I’ve learned that the greatest value you end up providing is determined by how you interact with your teammates. Are you a “Multiplier” (to steal a term from Liz Wiseman), or are you a “Diminisher”? I believe the engineering training I got gave me a lot of diminishing tendencies (i.e. not trusting others to do the analysis, etc.) But as a leader, I’ve learned that I need to let go of the reins, and trust others to do the job I believe I would do. Once you progress in your career a bit, it’s much less about what you can individually contribute and much more about how you enable others to be successful and provide multiples of value to your company.

Who is one person, dead or alive, who you admire? Why do you admire them? 

Ok, this one may be fed by recency-bias, but Taysom Hill. Taysom had 4 season-ending injuries in college but still put in the work to make a run at the NFL draft. Despite having a super impressive combine he didn’t get drafted but made every opportunity count in his first preseason with the Packers. He still got cut, but was picked up by the Saints. He then made himself into whatever the Saints and Coach Sean Payton needed him to be. He didn’t sit back and say “No I’m only a QB and I can’t risk getting hurt”. He did whatever he could to provide value, and he’s subsequently become one of the most talked-about players in the NFL, playing virtually every position on the field. For me, Taysom is an example of the value a great “generalist” can provide, which I see all the time in startups. He’s also shown an incredible amount of grit and determination to never let his dream die after so many setbacks. 

What habit or practice helps you manage stress? (the more specific you can be, the better)

You have got to keep your whole life in balance. You have to eat right. You have to exercise. You have to talk about your worries, anxieties, fears with someone — they can’t only live in your head. Proactively manage your mental health like you would your physical health. A few things I’ve done that have helped me manage my stress are: 1) I found a stress release through playing the piano. I suck at it, but it works a part of my brain that relieves the pressure I feel elsewhere. 2) I’ve worked with my doctors to get all my hormone levels tested and corrected. We figured out what was out of balance, and after some simple treatments, I feel like a new human being. Actually, I feel like myself again. 3) Talk openly about your stresses. Find someone you can confide in, whether that’s a significant other, a mental health professional, or even your boss. I’m lucky to have a boss who cares deeply about my mental state and has made it part of our regular 1-on-1’s to check up on me. In summary, you’ve got to manage your mental and emotional stress, or it will manage you.