So here we come into the end of 2020 and it is time to wrap up my twenty lessons in twenty years. It has been amazing to hear from the many people who have accompanied me on this journey; they have offered both feedback and encouragement for these subjects. It is hard to capture in words how much I have appreciated learning all of these things over the years, and I sincerely hope that people can use what I have written on their own quests for meaning.
If you are joining us late, here are links to the original three posts.
Without further ado, here are the last of my twenty lessons:
Choose Your Boss
I think that this is probably one of those things that you should learn earlier in your career than I did in mine. Your boss really matters for quite a lot. Your boss is more than someone who approves your expense reports and decides how many stars you get in your end of year review. Your boss ought to be considered a source of training, guidance, and experience. I will admit to having bosses I did not enjoy working with, and many I have considered great friends. When I am hiring other people, I try to market myself for what I can do for them as a boss to help them accelerate achieving their career goals. It is only recently that I realized that I never put my own early career choices through that lens.
It really matters for more reasons than I can put words to. There are a handful of people I have worked for whom I would work for again. There are a slightly larger number of people I have worked with as a peer whom I would work for as an employee. There are even a small number of people who have worked for me whom I would consider working for similarly.
If you find yourself in a situation where your boss is not helping you enough, then you should contemplate how to fix that. You should give that person the courtesy of a year if at all possible and then figure out how you can gracefully transition to something else that makes more sense for you.
Put Your People First
This is also one of those things that took too long for me to learn but I truly appreciate. You have to put your people first. I have suffered for this personally a few times over the years, but without regret. I have forsaken some promotions and tried to structure compensation and rewards according to this principle. There was one time when we were working at a struggling startup when I suggested to leadership that we offer each employee in the company a $1000 reward for hitting a very important milestone. We jokingly called it “The Grand Bonus”.
This may not have meant much for some of our most senior people, but I will say that it made a lot of difference for our more junior team members and people in roles that were not as heavily compensated as engineering.
Quite a few people on the team realized this, and I think they worked harder to get the milestone completed for the sake of making sure everyone was rewarded.
Watching people on this project, and how they adopted a caring attitude for their team in taking this project over the finish line for the benefit of others was humbling.
There are many times I have seen people go above and beyond to help other people professionally.
At the same struggling startup, when the end finally arrived, I spent three weeks after we closed our doors ensuring that I could do the most to help place our people into new roles and careers. That was painful for me financially as a parent; however, at the end when we had finished placing the team members into new roles I felt like a great burden was lifted. I would work with just about everyone from that team again—they were all amazing people.
The Serenity Prayer
I have commented on this before. I find myself quoting variants of the Serenity Prayer to people at work:
God, grant me the serenity to accept the things I cannot change,
courage to change the things I can,
and wisdom to know the difference.
I do not know how much more explanation that needs. Quite a few of the lessons I have learned over the years revolved around me trying to move items from one category to another. There are many times I tried to change things I could not, and many times I did not possess the serenity, or patience, to accept things that I could not change.
It is a great first-pass filter for events happening around your workplace and in fact the whole world around you too. 2020 as a whole, for example, is a master class in things we probably could not change. I am sure we are going to look back at this year for all of the things we did and scrutinize what we did with that time and how we applied serenity, courage, and wisdom to reach those outcomes.
Manage Excessive Risk
I have recently been speaking with one of my peers about their long-term career goals and how they can get there from here. Quite a bit of the road ahead of them is fraught with risk. The challenge now for them is that they will not get to take on some of that risk at their current company, nor will they get a job tackling that risk if they make a lateral move to another company.
This puts someone into a real chicken-and-egg situation. There is a solution to it, however. They are going to need to make a substantive life-change to increase the risk profile of their career.
If you are a director-level person and you want to break into your first vice president role, you might find that all the seats in your current company are taken for the next few years. There might be a clear succession already established or you might have better-qualified peers. This is one of those situations you should look at carefully for what you ought to do next.
Making the transition from one category of responsibility to another is hard. This is one of those times when it might make sense for taking a professional sidegrade. The challenge here is that you have to look at the size of the business and the size of the role accordingly. If you are too long in your current role at your current employer you might need to find a smaller company with a smaller number of existing directors and vice presidents to increase the chance you will get a viable promotion that suits your career goals.
The challenge is that this constitutes a very significant risk.
If you are only making changes to the risk you are managing at work, you are not going to accelerate your ability to transcend it. Sometimes you are going to have to take on more responsibility professionally than people will give you currently, and the only way to do that is to take a leap of faith into a new role.
This is an excessive risk; however, if you do not take excessive risk, you will not reap outsized rewards.
I am now spending some of my time with former coworkers helping them evaluate their career goals and the amount of risk they are managing. Some of these conversations are weeks old, some of these conversations are years old. In almost all of them, they are taking excessive risks to accelerate their careers.
It is terrifying to do that, honestly. I am relieved for them that they are not doing it alone, and happy to help coach them through the evaluation process and sometimes even the negotiation process that ensues.
Make Time For Little Things
The last lesson I learned that I want to leave you with is the importance of the little things. Downtime. Books. Hobbies. Cooking. Side projects.
Please make time for little things.
Writing every Sunday morning for me is one of the little things, as is a Saturday morning ritual to make a full pancake-and-eggs breakfast for the family. I make time for these things the same as I make time two nights a week for World of Warcraft raiding.
No one will force you to have a hobby or to do little things in your life for yourself or other people. You are going to have to carve out that time explicitly and just make it happen.
I am pleased that, in the most recent months, I have inspired someone to commit to writing more, as well as helped a friend build a small application that we will be publishing and talking about here in the new year.
With everything going on in the world today I picked up a small gardening hobby as well as committed to taking thirty to forty minute walks every day since I no longer commute to work.
I also explicitly make time every week to connect with someone not related to my current job. Either I am reconnecting with a former coworker or classmate, or meeting someone new on Lunch Club. Almost every single one of these meetings has been instructive or educational for me or for the other participant in some way.
Take a look at your weekly routine and if you are consumed with obligations, you should take a step back and ask yourself what you are doing for yourself, and what you are doing for your family. It is easy now, with all the electronics, to be answering emails and Slack messages around the clock. World events may have infected you with an unrealistic sense of urgency to be omnipresent professionally. I am not certain that is healthy. I have taken some mindful steps to ensure I have mental space and time for little things.
You should too.
And that wraps it up for my twenty lessons! Please share my statements of supreme obviousness on the socials, tweeter, facebake and linkum. Give me some likes, clip-claps, and stars. The more you reward me for writing, the more I will feed you. I believe this is equitable, and I hope you agree.
Thank you for reading along and I hope to engage with you in deep discussions on things to help us all be a little better every day!
