Chris Jenkins


Advice to my younger self about career and ambition

October 25, 2019

Not even hindsight is 20/20.

I’d like to try to condense some learnings from my career into a list of things I wish someone had told me when I started, and then write more about each of these things separately at my leisure.

When I entered the workforce, I was optimistic and excited, but there were so many things I didn’t know that I wish I did. I was so ambitious, so driven, and I wanted to make everything better wherever I went.

In practice, I’ve cycled between that optimism that I can do anything, and feeling cynical about the whole system, losing faith in myself, and wanting to give up.

The one thing that’s never been an option is giving up. Maintaining consistency and continuously learning wherever I can has helped me achieve some of the things I’ve wanted to, but with growth comes increased ambitions.

I don’t expect this list to stop growing either. Some of these thoughts undergo additional refinement every year, and I don’t believe you ever stop learning.

In no particular order:

  1. Businesses are organized machines that use people, processes, and materials to create products that generate more value than what is consumed. The excess value is profit and it’s what drives the current climate of private equity and institutional investment in companies that can’t ever be profitable (although the tide may be turning there).
  2. Because of this, it’s important that as an individual employee, you understand how you contribute to the benefit of this system. You should tie yourself to revenue generation if possible. In sales and marketing, this should be easily quantifiable. In engineering, it depends on how your executive leadership views your team. Are you a cost-center that’s a necessary evil, or are you a profit-center, a key component that is directly attributed to increased sales and revenue? You want the latter. Patrick McKenzie has a great article on this.
  3. “Politics” are not inherently bad. Anytime there are three or more people trying to accomplish a goal, you have politics. Wherever groups or subgroups can exist in parallel, you have issues of communication that many people call office politics. The desire of an organization should be to encourage open, democratic platforms of communication, and discourage secrets, ambiguity and obscurity that often occur and allow bad actors to manipulate the system in favor of their own goals. The game is always being played, so refusing to play it is tantamount to losing. The way to win (in an ethical org) is to also be ethical, and uphold the standards of the group.
  4. It’s impossible to draw hard lines around your “work” and your “personal” life. What you do in one affects the other. Early in my career I was hesitant to give up my personal life to my coworkers, but that dehumanizes the workplace. As with everything else I’ve said, this all requires balance, but don’t buy into the lie that you can compartmentalize your life. Optimize for overall happiness/success/other kpi you care about across your “holistic life”.
  5. In a lot of places you’ll find that the leadership doesn’t have extraordinary abilities that you don’t also possess. You will rightfully think that because of this you should also be able to accomplish things like they did, and probably with more success. It’s probably also true. Don’t let it go to your head though, because what you can’t see is the pain and opportunity cost of going down that road. Don’t go down this road without partners that care as much as you do.
  6. Find diverse mentorship. It’s important to get as much exposure to as many different disciplines as possible, and find thought leaders in each of those areas. It’s also important to have more than one mentor. It was really easy for me to hold onto all information and use it as my truth early in my career. Being able to discern good information from bad information is critical for growth in whatever discipline you are pursuing.
  7. Organizational change is incredibly difficult. You have many barriers as a young employee. Other employees will aggressively defend positions that threaten their livelihood, even if making that change is necessary for the good of the company. You won’t be able to win every battle, so choose the ones you know you can win, and be an advocate. Find a community within your org that can support you.
  8. Don’t buy into the grind until you’ve bought into why. I’ve consistently struggled with feeling like I need to do something, and I wasted time trying to make something happen without really truly having a purpose. Hard work needs a worthy application to be meaningful.
  9. Remember that your purpose as an employee is to create more value than you consume. Avoid opportunities that require you to devote the entirety of your waking moments working toward that purpose. Multiplying value should be good for you personally, you should feel like the company you are working for rewards extra effort according to what you put in. It’s good in your early career to put in extra effort if possible, especially if you are learning or behind the curve, but once you can put numbers to the value you generate, you should seek to find equitable relationships with companies that desire to take care of you for that extra effort. Don’t hurt yourself just to increase shareholder value.

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