How taking risks and thinking ahead can help you chart your path to career success

Nathan Tanner knows a thing or two about building a career. Taking the lessons he learned from pivoting careers from Finance to HR, and getting laid off after 6 months from graduating college, Nathan published Not Your Parents’ Workplace to share the lessons he learned so others could learn how to chart career success. As the Head of People Ops at Doordash, Nathan is constantly thinking about how his people can build successful careers, and he took the time to share his approach to transitioning careers, how professionals can take risks to fuel growth, and to share his own view on achieving career success.


CareerSchooled: After writing a book about your career journey, creating a monthly newsletter, and being a featured career strategy columnist at The Muse, I think it’s safe to say you’ve learned a thing or two about careers! Since you began your career, has your view and outlook on careers evolved or changed? How so?

Nathan: I learned a lot of valuable lessons early in career, mostly through trial and error. I published Not Your Parents’ Workplace with the goal of sharing those lessons with young people so they could find their dream job and be successful in their careers.

For the most part my outlook on careers is similar with the exception of risk evaluation. A year or so ago I heard a podcast interview with Chase Jarvis where he said, “This is the first time in the history of the world where the risky thing is to do the traditional thing.” I think there’s a ton of truth to that. When I got laid off from my job 6 months after graduating college, I spent all my time looking for jobs, mostly corporate jobs. If I could do it over again I would have looked harder at startups or maybe even tried to start something myself. At the time I viewed those options as being too risky.  

I think that always doing what we’re told and playing it safe in our modern, dynamic economy may lead to situations where our skills become obsolete. Many of the career moves I’ve made over the last few years were viewed as being risky. But I think the riskier move would have been to stay put and do nothing. Often times the “safe” option is actually the risky option.   

CareerSchooled: You’ve pivoted roles, functions and industries a number of times in your career. What has enabled you to transition into new opportunities?

Nathan: Most of the career pivots have been relatively minor, but leaving the finance world to move into HR was a big one. When recruiting for jobs I was really concerned that I wouldn’t be competitive because I didn’t have enough HR experience. I eventually learned to abandon that way of thinking. I started telling companies that not having HR experience was a positive and that’s actually the reason why they should hire me. I’d share how my finance experience taught me many invaluable skills which would allow me to bring fresh perspective to a field that is fairly traditional. Career changers tend to be overly concerned about areas of deficiency, but it’s critical to focus on how our unique experiences will set us apart.

CareerSchooled: How do you know when it’s time for a change, whether that’s to a new job, or a new career?

Nathan: I think the answer depends on whether you’re looking at changing jobs or careers. When evaluating whether to change jobs, the most critical thing to consider, in my opinion, is skill acquisition. Are you still growing? Are you learning things that may be valuable in the future? What skills are you developing? If you’re not constantly learning, I’d be a little concerned, especially if you’re early in career. Stagnation is the enemy of career satisfaction.

Evaluating a complete career change is more nuanced. One question I encourage you to ask yourself is whether you can, or even want, to become world class in your current field. I was a decent finance professional, but it always felt like work. I rarely got excited to analyze financial statements or build a new financial model, but many of my peers lived for that stuff. Eventually I reached the point where I knew I had to change careers and I spent a lot of time identifying a field where I could be world class. Here’s an article I wrote that goes deeper into this topic.

CareerSchooled: As an applicant, it can be a challenge to stand out when you are going against other candidates who have more direct relevant career experience. How can you stand out if you are changing careers?

Nathan: If you’re a career changer, it’s really hard to get a job coming through the front door (AKA, applying online). I recommend focusing your efforts on getting in through the back door. What I mean is that those tasked with reviewing your application, whether they be a recruiter or machine, likely won’t know what to do with you. Career changers don’t fit the mold so they often get rejected.

Coming through the back door requires you to be more proactive. You’ll need to build relationships You’ll need to network. I’ve found informational interviews to be extremely effective (I wrote a 10 page guide on this topic here). These methods require more work, but they put you in the driver’s seat which allows you to tell your story rather than waiting to be picked.

CareerSchooled: What advice do you have for professionals who are thinking of making a career transition?

Nathan: Don’t just look at your current job. Look at the job you’d have five and ten years down the road should you stay on your current path. I’d get on the phone or grab lunch with these people. I think many jobs early in career aren’t that interesting so it’s important to get a sense of what’s to come in the future. If you don’t like your current job function and you’re convinced it’s not going to get better as you advance, I’d start learning about opportunities that may be a better fit..

CareerSchooled: What do you define as success for you in your career?

Nathan: A few years back I was eagerly anticipating a promotion. I thought that when the promotion came I would be happy and I would finally view myself as a success. But a funny thing happened. Within a week or two of getting promoted, I started focusing on the next career milestone. I then caught myself thinking that I’d be successful once I reached that new goal.  

I recently heard an interview with legendary coach John Wooden. In it, Wooden shared his personal definition of success. He said, “Success is peace of mind, which is a direct result of self-satisfaction in knowing you made the effort to do your best to become the best that you are capable of becoming.”

Wooden’s words taught me that individual success comes less from extrinsic rewards, which we don’t fully control, and more from personal growth and development, which we completely control. If you can look back at the end of the month or year and say that you’ve done your best and that you’ve grown as a professional, then I say you’re a success.

One thought on “How taking risks and thinking ahead can help you chart your path to career success”

Leave a Reply

Your email address will not be published. Required fields are marked *