Career Q&A with Ann Hiatt, Leadership Consultant and Former Executive Business Partner to Jeff Bezos and Eric Schmidt (#5)

I recently kicked off a series of Career Q&As with successful leaders. The goal is to provide practical advice and insightful lessons you can leverage to further your career. Next up is Ann Hiatt, a leadership consultant, and the former Executive Business Partner to Jeff Bezos and Eric Schmidt. Ann offers great advice on taking career risks, trusting your intuition, and effectively managing stress.

Ann Hiatt received her initial business training during 15 years as the Executive Business Partner to Jeff Bezos (CEO of Amazon) and Eric Schmidt (CEO and Executive Chairman at Google/Alphabet). Ann now consults with executives of Fortune 500 companies as well as European and Silicon Valley startups and is on several advisory boards. Ann has recently relocated from Silicon Valley to Europe and brings with her a unique perspective on what it takes to succeed in business today and how to apply that to any organization. She is also a sought-after international speaker having spoken at conferences across five continents.

Ann is a native of Seattle and studied International Studies at the University of Washington before moving to California to begin a Ph.D. at UC Berkeley. She speaks Swedish fluently and Spanish conversationally among other European languages. In her elusive free time, Ann enjoys running, scuba diving and traveling.

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

I love anything written by Adam Grant. His book, Originals, is a favorite of mine since I’ve spent 15 years of my career surrounded by and collaborating with truly original thinkers and am fascinated by them. His insights and research really ring true for me. Also, he’s a spectacular human being. If you’re not already following him, you should!

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

My first job ever was at a startup in Redmond, Washington in 1995 (back before anyone knew what a startup was). I learned from the entrepreneur founders (who were also brothers) what it’s like to start your own company, land your first clients and grow your first team. I had no idea how much that job was preparing me for my future career at Amazon and Google and beyond. 

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

I almost killed Jeff Bezos two months after being hired at Amazon in 2002. Seriously. Luckily that isn’t the end of the story or my career.  While it was the worst day of my professional life, it taught me that no matter how spectacularly you fail you always learn something. When the helicopter that I hired for Jeff Bezos crashed with him inside I learned that I am really good under pressure and with crisis management.  I just hope to never need to use that skill in that way again!  

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

I would say to take big risks early on. Don’t be afraid to ask the “dumb” questions or to show lots of ambition.  You will never ever receive anything if you don’t ask, so be bold! I wish I had learned that lesson 10 years earlier than I did.  Oh, and max out your 401k savings contributions every year—especially in those early years. Compound interest is your best friend! 

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

I have been lucky to work in very innovative companies and teams. With that said, there have been times when even those people told me no when I wanted advancement. I had to trust my gut, rather than listening to advice to be happy with what I had, and push harder to find creative ways to accomplish my growth goals. Eventually, that meant taking the scary step of starting my own venture.

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?

Be bold! Aim much, much higher than you can currently imagine. 

What’s one of your proudest professional accomplishments? 

Most of my proudest moments involve creating success within impossible circumstances. At the moment that means building a 6-figure consulting business in less than a year after leaving Google—all while in a new country, language and network.  I love helping global entrepreneurs thrive!

What’s something unexpected that has happened in your career, and how have you responded?

My very first job out of university was working for Jeff Bezos at Amazon. That came very unexpectedly and literally changed the course of my life. I learned not to fear failure, to be bold, and to trust my instincts. 

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

When I started at Amazon in 2002 I was timid and deferential. That didn’t last long!  In order to survive in that environment, you have to be daring and confident. Those lessons served me well when I left Amazon to start a Ph.D. at UC Berkeley and then in my 12-year career at Google as the Chief-of-Staff to the CEO. Now as an independent consultant I use those skills and experiences every day with my CEO clients. I am so blessed to have learned to be proud and confident whether I’m on stage, coaching a CEO or in a one-on-one mentoring session. I still have moments of doubt and imposter syndrome, like most high performing people, but I’ve learned how to combat.

When have you felt stuck in your career? How did you break out of it or push forward?

I loved every minute of working at Google but eventually decided to leave in year 12 because there weren’t opportunities for me to grow there. I had hit a ceiling that felt arbitrary and I wanted a bigger challenge. I realized that that kind of challenge would only come if I took a leap of faith in myself and started my own company. It’s been both terrifying and very satisfying.

Who is one person you admire? Why do you admire them? 

The notorious RBG! Ruth Bader Ginsburg is a pioneer who has broken glass ceilings for so many people. She is brilliant, clever, quirky and unapologetically herself. 

What habit or practice helps you manage stress? 

I had a full-on midlife crisis a few years ago and found that exercise is my very best form of therapy. (Although I did talk therapy as well!) I find now, even when life is happy and calm again, that I need protected time every single day to move my energy out of my head and into my body.  I need the sunshine and fresh air and relentless pace to keep me grounded so that I can then do my best mental work. In true Silicon Valley form, several years ago I signed up to run a half marathon to raise money for charity before I had ever even run a 5K. I am happy to say that I completed that goal (several times over now) and felt very strong and proud at the end—which was exactly what I needed at that moment in my life. I have continued these physical challenges to myself which helps my drive and confidence in all areas of my life.

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Career Q&A with Scott Smith, CEO of CloudApp (#4)

I recently kicked off a series of Career Q&As with successful leaders. The goal is to provide practical advice and insightful lessons you can leverage to further your career. Next up is Scott Smith, CEO of CloudApp. He has a lot of good nuggets throughout and I particularly like his advice on spending as much time as possible feeling uncomfortable, how he balances work and family life, and the power that comes from assuming positive intent.

Scott Smith is CEO of CloudApp, whose mission is to enable instant business communication through quick shareable videos and images for its 3 million users. Before CloudApp, Scott spent three years at Facebook developing and launching the ‘Workplace’ collaboration tool. He joined Facebook through an $85m acquisition of Parse, a YC-backed developer tools platform. Before that, he spent three years at Dyn building its sales and partnership channels. Dyn would eventually be acquired by Oracle for $600m. He’s a dad of three of his own, and foster dad too. You can find him on Twitter at @scotcha1.

Scott Smith headshot

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

“The Hard Thing About Hard Things” by Ben Horowitz. In the book, Ben tells a story about when he joined a brand new startup. His daughter had just been diagnosed with an illness, and he was extraordinarily busy and stressed. He spent a lot of his time thinking about his job, and himself. One day his father came over to visit, and as they sat and talked, his father said: “Ben, do you know what’s cheap?”. Ben replied, no, and his dad said flowers. He then said “Ben, do you know what’s expensive? Divorce.” 

His father was reminding him to refocus on what was most important — his family and their well being. This idea of family as a focal point in life has always been important to me. The idea that “No other success can compensate for failure in the home” is something that motivates me, and Ben’s book really resonated with this on a very practical level. 

My family keeps me grounded and focused. But frankly, the idea of family is often understated or shied away from in Silicon Valley. Most of us here are desperate to win, succeed, or to gain some level of notoriety. I loved the honesty and vulnerability that Ben showed in sharing that story. And it’s helped me throughout my 10+ years of marriage to always be reminded of how I got to where I am, and what’s most important.

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

When I was 19 I left the United States for 2-years to do a service mission in Birmingham England and Cardiff Wales. I can still remember my very first day as a full-time volunteer. I was picked up from our training center and I was immediately taken to the Birmingham City Center “Bull Ring”. The ‘Bull Ring’, was a popular shopping center booming with tens of thousands of people walking around. My leader said “Okay, go find someone to talk to” and he quickly disappeared. I looked around shocked, and very concerned, but made the decision to say “Hi” to the next person who walked by. From the moment I entered the UK, I was perpetually in a place of discomfort being asked to do hard things. And while it was hard, this experience allowed me to learn to embrace discomfort and try things that made me uncomfortable.

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

At the age of 11, I tried out for the 11 & 12-year-old Milburn All-Star baseball team. For years I had been a well recognized, and fairly successful pitcher throughout our local little league, but when the list came out showing who had made the team — my name was notably absent. That team went on to play in the Regional Championships just shy of the Little League World Series. The team traveled all over the Northeast Region, stayed in hotels, were featured on TV, and they played against some of the best teams in the nation. 

I was really discouraged and disappointed to have not made that team. It was one of the first times in my life where I really felt the weight of what a future could look like where you might not be good enough despite your best efforts. While I can’t say that moment was the catalyst that led me to be the greatest pitcher in MLB history, that memory and moment has left an indelible mark in my mind and life of a feeling I just hate to experience. Failure is important, and it helps us grow, but I absolutely hated the feeling of coming up short, and ever since then it’s motivated me to work harder.

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

My advice would be to spend as much time as possible feeling uncomfortable. Stretching yourself to try new things, and to say yes to things you might not have all of the information for.  One of my favorite moments as a very new sales rep at Dyn (my first full-time job after college) was when they invited me to work at their booth at a conference in Santa Clara, California. I had only just recently joined the company several weeks earlier, knew almost nothing about the product, and the first person I spoke to at the booth was a high ranking technology officer at Cisco (I’m pretty sure it was the CTO!). 

As I looked around me, hoping to receive help, no other team member was jumping in to help me, and I realized I was all alone. I stretched the knowledge I had about the product as far as I possibly could, and surprised myself when we ended the conversation several minutes later. Reflecting back on this experience, it all started from saying ‘Yes’, when my VP Sales, Kyle York, asked if I’d be willing to attend this conference last minute and fly across the country.

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

I hear bad recommendations all the time. But I also have a career behind me full of perspective. I think the worst kinds of recommendations are given without any context. These are recommendations that someone you are meeting with tells you before they understand your situation. Silicon Valley is full of thought leaders and ‘yogis’ who tell you their way is THE way. 

I think rather than providing a list of bad recommendations, and the ones to avoid, I’ve always tried to follow a relatively simple process that my dad suggested to me years ago when I started playing little league baseball. While I was young, every year I had at least one new coach. Each coach had different suggestions. Some would tell me to throw curveballs, others would tell me to carefully avoid them because they would hurt my arm. Other coaches would recommend I change my batting stance (move forward, or backward, change my hand grip). All of the suggestions came from a place of good intent, but if I changed my approach to the game as quickly as I was asked to, I wouldn’t have been able to keep up and it would have severely affected my game. 

In the professional world, any time I hear what seems like a great idea that might require me to change, I write it down, think through it for a few days, and consider how it could fit into my current approach. I also always tend to be a Googler of new ideas. I love to find other people who might have tried out the approach and to hear their experience. But what I’ve found to be the most compelling and powerful, is to, over time, build a group of people I respect and trust, who I can ask and solicit feedback from. So my recommendation is basically to take recommendations carefully and thoughtfully but to always be open to them.

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?

Always assume positive intent. This is a philosophy that I now live by, that has largely changed my work experience. By positive intent, I simply mean, when someone does or says something, choose to believe that they are acting with the intent of good. That they are trying to provide good feedback, or they are trying to help improve your product. Never choose to be a victim. Rather than spending time or energy believing that the person hasn’t put in their best, or that they are trying to do something that is hurtful to you, spend your energy and time believing that they have your or your companies best interests in mind.

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

On April 25, 2013 Parse was acquired by Facebook for $85m. This felt like a significant event for me because it demonstrated that we, as a small 20-person team, had built something so incredible that one of the largest companies in the market wanted us to join them. We even received an email from Mark Zuckerberg welcoming us to Facebook, expressing his desire to include us in his larger vision for the future of their developer business. But, maybe even cooler, and on a personal level, was that Parse was mentioned during a segment of Facebook’s quarterly earnings call. On that day, I received a call from my father in law who had mentioned that it was ‘pretty cool to hear about your company in the Wall Street Journal today’. 

What’s something unexpected that has happened in your career, and how have you responded?

When Parse was acquired by Facebook, we were all very surprised. We were brought together at a small all-hands meeting, and our CEO, Ilya Sukhar, excitedly (and a little anxiously), described that we would be joining Facebook. The team instantly had a million questions. Would we need to move our office from SF to Menlo Park? Would Facebook shut us down, like so many companies before it? Did we all have jobs still? The questions were many that day, and even after our CEO patiently answered many of them, our team was unclear about our future, and you could sense a general feeling of discomfort. 

After joining Facebook, it became very clear that there were some incredible opportunities in different and adjacent parts of their business. Facebook, for example, had a larger, and more mature, developer partnerships team. Rather than trying to go about everything alone at Parse, developing relationships and partnering with that team seemed like an obvious way to continue to grow Parse within Facebook. 

While on a developer relations trip in Europe, I had dinner with a Facebook director named Julien Codorniou. He was charismatic, energetic, and I felt like he had a great grasp of Facebook and its future. After meeting him, I reached out over email, and we developed a relationship that led to me joining his team. While my initial experience going through the Facebook acquisition was unexpected, I was able to leverage Facebook’s strengths to provide myself and Parse with a larger platform.

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

When I was in high school and college, I tended to frequently just ‘show up’ at classes, and tests. By ‘show up’ I mean to say that I either did little or no preparation. Looking back now, I’m not sure why. But I wouldn’t be caught dead doing that today. One of the biggest changes for me has been to realize that doing your best work takes an immense amount of effort and preparation. The workforce is a grind. You commonly hear the phrase, “Choose a job you love and you’ll never work a day in your life.” I don’t agree at all with that phrase. Work is a grind, and you need to be ready to grind. While I regularly get to experience the excitement and love for my work, I also regularly have to experience the deep troughs of failure, regret, and discouragement, and I still need to press on, prepare, and deliver what’s expected of me.

When have you felt stuck in your career? How did you break out of it or push forward?

9 years ago, I moved from the Manchester New Hampshire Dyn office, out to San Francisco to open a small west coast branch. I had, in large part, moved from the East Coast to the West Coast to be closer to family. My dad recently had back surgery and I wanted to be closer to support him in his advancing Parkinson’s Disease. 

Dyn provided a wonderful experience for me, but when I moved out West, I admittedly had underappreciated how hard it can be for a small branch to feel important to a primary headquarters. Not to mention the fact that I found it incredibly hard to transition from an incredibly beautiful 20k+ square foot office in Manchester to a literal 15×15 foot room with white walls and no windows. Just a small box for me to work in. My team and leadership were now remote to me, and it was a challenge to feel included, and supported. 

I pretty quickly felt like I was on an island, and I felt like over time there would be few opportunities for advancement given the low interest in growing that office by Dyn. As I started to go on more local sales calls, I frequently heard from the CEOs that were my customers that they would be interested in hiring me. I was admittedly a little surprised to hear this, but I started to become open to the idea of finding something better suited for my career track and interests. 

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

For the entirety of my 10+ years of marriage, my wife and I have gone on a date night nearly every single Friday. The date night is pretty simple, and it usually follows some kind of template: whether it’s dinner and a movie, games and dinner, visiting a bookstore, or occasionally knocking off a few high priority to-dos at Home Depot. 

The main ingredient that I feel that is critical, and honestly the priority of the night, is the personal, devoted, and focused time spent building a relationship with my wife. We have 4 kids all under 8, and life can sometimes be pretty wild at home after work and there are few opportunities for quiet and peace. Quite literally, they seem to try and interrupt any and every conversation we try to have. 

The date night allows me to end the week, put down my phone and computer, and to begin to release and put down some of the stress I’ve been carrying. It helps me connect with a person that provides me with so much love and support, and it helps us put the week into perspective, and go into the weekend a little more slowly. Plus, and I think this is most important, it gives you time to find out how your spouse is doing, to find opportunities to do things with them that they love, and to remind them that even if you’ve been distracted a bit earlier this week, that this time is just for them, and you can show them how important they are to you.

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Career Q&A with Eric Hass, Analytics Leader at Amazon (#3)

I recently kicked 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 next interview is with Eric Hass, an Analytics Leader at Amazon. I love his advice on taking action without asking permission, avoiding the law of averages, and habits for managing stress.

Eric Hass is an Analytics leader at Amazon. He’s spent the past 10+ years in a mix of data and business roles, from leading teams to launch new products to driving growth in mature $100M+ businesses. He’s currently leading a cross-functional team (data science, software engineering, product management) to solve personalization and optimization challenges on Fire TV and Fire Tablets.

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

One of the challenges to get the internship / job you want early in your career is that you may not have relevant experience for it. It’s a chicken and egg problem. This problem can also manifest itself later in your career if you want to change functions/industry, etc. My approach has been to find an opportunity to just start doing what I want to do before seeking a new job. A few years ago, I decided I wanted to transition from product/business management into data science and tech leadership, but I didn’t have a formal educational background in the area. I took on a project in my current role to develop a machine learning based product plan and did some self-study to learn the basics. I was able to leverage that experience to get an individual contributor role working closely with one of the most senior data scientists at Amazon. I focused on learning as much as I could in that role, and after a year was given the opportunity to lead a cross-functional team over science, engineering, and product management…So, my advice is to not wait for anyone to give you permission to do what you want to do. Just find opportunities to start doing it, and doors will open.

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? 

I would have prioritized getting educated in data science and computer science while in school. Being able to work with and lead engineers enables you to create value for customers at great scale, even if you don’t end up becoming a scientist or engineer yourself. I’ve learned a lot of this on the job and self-study, but I wish I would have prioritized it earlier.

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

I focus on three things: 1) Sleep, 2) Exercise, and 3) Boundaries and focus.

Sleep – Through trial and error, I found that I get more accomplished by getting a full 8 hours of sleep, than by sleeping less and having reduced energy and mental capacity throughout the day. I know others who seem to be productive sleeping much less, but a lot of research is coming out on the short and long term benefits of sleeping a full 8 hours. The Circadian Code by Sachin Panda was eye-opening for me.  I recently attended a presentation by a sleep doctor about the topics in this book and was fascinated.

A few things have really improved the quality of my sleep. 1) Time-restricted eating – I try not to eat after 6-7pm. 2) I try not to do any difficult thinking after 7pm (or else it’s hard to turn my brain off). 3) I try to maintain mostly the same bedtime / wakeup times 7 days a week.

Exercise – I used to tell myself that I didn’t have time to exercise regularly. However, I’ve found that it’s the best investment of my time that I make in a day. Last year, I re-worked my schedule so that I could exercise every morning and have felt more energized throughout the day to be at my best.

Boundaries and focus – I try to be disciplined about when I’m working / not working and don’t check work email after I leave work (except on rare occasions). When I’m at work, I do my best to block off time every day to work on high impact projects without distractions.

*This is still a work in progress for me and I’m always experimenting with ideas to reduce stress and boost my productivity. I’d love to hear any practices that have worked for others!

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

7 Habits of Highly Successful People and How to Win Friends and Influence People were foundational for me. I think that by following the principles in these books you can be fairly successful in almost anything.

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

I think there is a tendency to focus too much on averages when making schooling/career decisions.  Common guidance I see is to pursue opportunities where the averages are favorable. What is the average starting salary of someone graduating from this program? What does the average career look like for someone in this industry? What is a typical career path in this company? However, this line of thinking misses the fact that there are often huge distributions of outcomes, and it doesn’t consider the opportunities you may have to be on the extreme positive end of the spectrum or how you could customize your experience. 

What makes this challenging is that understanding what your true opportunity looks like requires that you have several exploratory conversations with people in the school/industry/company you are considering to see what’s possible, do some soul searching on what you would want your path to look like, and then do some critical thinking to assess how realistic it is and what alternative options you might have if it doesn’t work out as you hoped. 

This was very real for me when I was deciding whether to get an MBA. I wanted to get an MBA, but the ROI wasn’t making sense when I was looking at averages in terms of future career prospects. However, after dozens of exploratory conversations, I developed a specific path of where I wanted to take my career, and the numbers totally changed. It ended up being a great decision for me. Since then, I’ve gone through this exploration exercise at least once every few years. 

Career Q&A with Derek Pando, Head of International and Partner Marketing at Zoom (#2)

I recently kicked 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 second interview is with Derek Pando, Head of Int’l and Partner Marketing at Zoom. I love his advice on how to trust your instincts, seek out mentors, and be bold in sharing your career aspirations.

Derek Pando leads Partner and International Marketing at Zoom Video Communications. He has spent his career at high growth enterprise software companies including Salesforce and LinkedIn, where he helped launch LinkedIn Sales Navigator. He has held a variety of different marketing roles in his career. His expertise is in product marketing, international marketing, marketing strategy and social selling. He also writes and speaks on collaboration, technology, marketing, and professional relationships. He speaks Spanish fluently and can get by in Portuguese. If you a lot of time to kill, ask him about his vegetable garden. You can follow him on his personal blog (derekpando.com) or on Twitter (@djpando). 

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

This might sound strange, but the book that has influenced my career the most is the Alchemist. In it, the main character has to leave good situations in search of even better, often starting from scratch. Each time he encounters significant struggles but achieves greater success. I think many times in our careers we have to do the same to keep progressing to our full potential. Leaving a job that we like or where we are very comfortable can be very challenging, but thinking about the story and book has given me the courage to take a leap multiple times. 

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

After some encouragement from my dad, I started a lawn mowing business where I grew up in Texas at the age of 15. I quickly learned that if you showed up, did a good job and were respectful you would have plenty of customers and more money than a 15-year-old would know what to do with. Creating something, working hard and having it be successful left a lasting impact. That experience set a foundation for me to feel confident in my professional abilities. 

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

In college, I applied to my undergrad’s business school program. I was dead set on it. It was highly competitive and I got rejected. I was pretty devastated but tried to pick myself up as quickly as I could. I chose a different major, ended being the president of a club in the business program that I did not get in, got a scholarship and later returned to the same school to get an MBA. At the time, it felt like my clear path to success was destroyed, but things ended up working out better than I hoped. It was a good reminder that there are multiple paths to the same goal. 

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

After you are making $75k, don’t make any career moves based mostly on money. Ignore anyone who does not encourage you to save money in your 20’s.  

What’s one of your proudest professional accomplishments?

The most recent professional accomplishment that I’m most proud of is working on Zoom’s IPO. When I first joined Zoom, I asked our CMO that whenever an IPO happens, I want to be involved. She asked me to be on the IPO deal team when the time came, which was something I had never done before. I learned a whole lot and feel proud to have contributed a tiny piece to the most successful IPO of 2019. This was a good lesson to tell your bosses your goals and aspirations, they’ll often help you achieve it if they can. 

When have you felt stuck in your career? How did you break out of it or push forward?

Yes. Each time, I consulted with trusted mentors. One time they encouraged me to stay at a job where I felt stuck and just be more patient. At a later job, my mentors encouraged me to leave, both ended up being the right call at the time. 

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

Tyler Shultz, the Theranos whistleblower. That guy stuck to his guns and did what he felt was right against an unbelievable amount of pressure from very powerful people, including from his own family. It’s so hard to do the right thing in that situation, but he did.

What habit or practice helps you manage stress? 

Exercise. I managed the first two Zoomtopia events that had 500 and 1500 attendees respectively. It was a big project and very high stakes. As strange as this may sound, even though it was the busiest time of the year, I’d make sure to go running 1-2 times a week. Letting out some physical energy always seemed to help me not freak out. 

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?

Trust your instincts. Earlier in my career, it was so easy to default to the opinion of someone more experienced or older and not fight for my ideas or opinions. In hindsight, my instincts were better than I gave myself credit for at the time.

Thanks for reading. If you haven’t already, check out my Career Q&A with Dan Jimenez, Chatbooks COO.

 

Career Q&A with Dan Jimenez, Chatbooks COO (#1)

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!

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.

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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.

5 Habits That’ll Ensure You’ll End Every Day Feeling Successful

You know those days when you leave work feeling amazing, pumped that you were highly productive? On the flipside, I’m sure you have days that are just the opposite. Ones that leave you feeling frustrated, wondering whether you got anything done. What if there was a way to end every day knowing that it was successful?

Unfortunately, there’s no bulletproof formula to guarantee this, but there are certain practices you can follow that’ll help.

Here are five habits that, if practiced daily, can boost your success at work:

Click here to view the full article on The Muse.

3 Better Things to Do Instead of Obsessing Over Finding Your Passion

You’ve spent so much energy trying to “find your passion” that you’re exhausted. And while you’ve invested countless hours to discovering your dream career path—doing all the things you’re supposed to do, like setting up informational interviews, and growing your network—you feel like you’ve made little progress.

Is it possible you’re making it more challenging than it needs to be? What if it’s more about looking inward and less about going on one million coffee meetings?

I’ve seen this firsthand in my experience as a career coach. Most people I work with can’t identify their passion, and they stress over it. They devote too much time and energy into the process.

I understand: There are few things as frustrating as not knowing what you’re meant to do want to do or what’ll truly fulfill you. But the answer isn’t going to appear if you overthink it and analyze every little thing that happens in your career. And with that, here’s what I recommend:

Click here to view the full article on The Muse.

Just Lost Your Job? This Day-by-Day Timeline Will Get Help You Land a New One

You just lost your job. You may be crushed. You may be in denial. You may realize your work was toxic and be genuinely happy you never have to go back. Or, you may not fully understand how you’re feeling.

Regardless of your state of mind, it’s hard, and finding a new job can be even harder. Many people simply update their resume and apply for positions that look interesting. That’s one way to handle it, but it’s also likely to be insufficient. Plus, it’s important to give yourself time to process the loss.

I’ve been in the exact spot you’re in now. I was laid off from an investment bank at a time when finance roles were hard to come by. Through personal experience, and through my work as a career coach helping countless people find jobs, I’ve put together a comprehensive timeline of the steps to follow if you’re in this situation.

Day 1

The very first thing you should do after leaving the office…

Click here to view the full article on The Muse.

3 Realistic Things You Can Do When Your Career Isn’t Living Up to Your Expectations

When I started my career, I felt like I could accomplish anything. I hustled to land my dream internship, managed to turn that into a full-time offer, and was pumped to get started making my mark. I was confident that if I just pushed myself and put the time and effort in, everything would work out. I had high expectations for my future and was certain I’d succeed.

Less than a year later, the company I’d joined went bankrupt. My team was absorbed by its competitor, which only served to delay the inevitable: I was laid off a few months later. After a long period of unemployment (that probably felt much longer than it really was), I found another job.

Although it was a decent role at a respectable clothing company, it wasn’t what I really wanted to be doing. No matter how much I told myself I was meant to be in in the retail industry, I always felt out of place. I just wasn’t passionate about it and trying to force it only made me feel more dissatisfied. I felt like my career had derailed.

Getting my it back on track took time, and I learned several critical lessons along the way. If you feel unhappy with the path you’re on, consider the following:

Click here to view the full article on The Muse.

5 Questions That’ll Help You Pinpoint Why You’re Unhappy at Work

We’re all on an endless quest for happiness, aren’t we?

And there are certainly career benefits to pursuing this endeavor. Harvard Business Review reports that happy people are 31% more productive, have 37% higher sales, and are three times more creative than their peers.

There are countless habits and hacks that can help, including exercise, expressing gratitude, or starting a side project, but how do you know what will really make you feel happy in your career?

When I was in college, I stressed a lot about whether the career I chose would be fulfilling. I’d seen plenty of people who were miserable in their jobs, and I wanted none of that. As I sought advice from friends and family, I was frequently told I should “do something I love” or “pursue my passion.” None of that advice resonated though because I didn’t yet know what I loved, and I worried that I’d never figure it out.

My path hasn’t been a straight line, and I’ve had my fair share of setbacks, but I’ve learned a lot along the way.

By asking myself the following five questions throughout my career, I’ve been able to pinpoint causes of my discontent and determine what changes I needed to make to be happy.

Click here to view the full article on The Muse.