by Stew Bradley March 11th, 2020

A career transition is one of the most daunting changes you can make in your professional life. Career transitions are more than simply changing jobs, they are discontinuous shifts in your career track. This isn't to say that changing jobs is an easy task, in fact, quite the opposite. A job change requires adapting to new coworkers, culture, responsibilities, and expectations, each of which are challenging. A career transition takes the already formidable challenge of a job change and adds wrinkles, like; having to learn a new industry, starting a company from scratch, or taking on a role that has little overlap with your prior work experience.

Let’s use professional sports to illustrate the difference between a job change and a career transition. A job change would be an NFL quarterback leaving the New England Patriots to join the Tampa Bay Buccaneers. The quarterback will have to adapt to a new (locker room) culture, teammates, responsibilities (playbook), and expectations, but his role is largely the same; playing quarterback for a football team. A career transition on the other hand would be akin to an NFL quarterback joining the LA Lakers (for the uninitiated the Lakers are a basketball team). In addition to the requisite learning of joining a new team, the quarterback would also need to learn an entirely new sport. The latter is clearly more challenging.

Many of the founders/operators I most admire —Phil Knight, Jeff Bezos— went through career transitions before landing in the roles they now are known for. I’ve made several transitions myself —some more drastic than others— and each presented unique challenges, taught me valuable lessons, and added to my growing fascination about what made career transitions successful.

My first career transition was leaving my job as an NFL linebacker to take a banking job at Goldman Sachs. Despite being an accounting major in college, after spending seven years playing professional football, I was ill-prepared for entry into the corporate world. How did I survive?

Three factors:

  1. I had the support of people who believed in me, and were willing to help via direct constructive feedback.
  2. I put in the work outside the office [i.e. lots of reading].
  3. I found the similarities between my new role and prior work experience and used that as a foundation while I learned.

At first glance, there seemed little in common between the two jobs, but upon deeper review I was able to find some transferable skills and similar work dynamics. The first was team structure, as both football and banking are done in teams where each member has a clearly defined role. Trust in your teammates and focusing solely on your portion of the task leads to the best results. The second was the high stress environment common to both banking and football, where the ability to keep calm under pressure is vital to success. These similarities, albeit few, gave me a foundation to build on as I scrambled to learn on the job.

My second career transition, leaving my banking job at Goldman to become a hedge fund analyst, seems notably less drastic than my first. The work product was similar (i.e. building financial models), both were in finance, and from the outside (as my mother told me several times) they seemed like the same. But the adjustment felt almost as jarring as when I first left the NFL. Investing requires decision making with imperfect information and taking views that are often contrary to the broader consensus. This was a risk I had no experience with, so despite the external similarities, the role felt completely foreign at first. I found success by following playbook that worked during my first transition. Leveraging support and feedback of the people around me, putting in the work, and anchoring to the similarities between my previous and current roles as a foundation while learning on the job.

Starting a business is the quintessential career transition. All of the challenges of a 'typical' career transition are not only present, but magnified. Instead of adapting to a new environment, that environment needs to be created from scratch. And unlike a typical work transition, the learning curve for a founder/operator does not slow for a very long time. The need for founders to constantly evolve as a company scales is too rarely discussed. Managing a fast-growing company can feel like a career change every few months. This is made even more difficult by the lack of clear demarcations when the demands of the job change. Running a three person company is clearly different than a company of three hundred, but how different are the demands between a 3 person and a 5, 10, or 15 person company? The change in the skills required to succeed is gradual, and without actively working to expand an operator's toolset, the gap between what the company needs and what an operator can handle can become too wide to overcome. The three pronged approach I used in my transitions is something we have found successful for operators.

  1. Find people (partners / mentors / investors) who believe in you and are willing to help and give you candid constructive feedback.
  2. Put in the work. No shortcuts here.
  3. Find common ground with your prior experiences and use that as a foundation to grow.

While this may sound daunting, the need to evolve can be one of the most exciting parts of building a business. A proclivity to honest self-assessment makes this process feel more organic. But even operators who bristle at the idea that they need to improve, quickly adapt when they grasp the potential benefits to their business if they continue to evolve. Applying these lessons to myself has been critical as El Cap continues to grow, and helping operators along this journey is one of the best aspects of my job.


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