Good morning and hello! It is time for part two of my four part journey through twenty years of hard-learned lessons.
I have tried to group them loosely into four sections that each cover five-year chunks of my career. The first set of five lessons was mostly stuff I learned while I was still feeling invincible, and could code my way out of any problem. This next set of lessons is stuff that I was learning while slowly realizing that maybe I should consider approaching my problems differently.
So let’s jump in!
Lesson the sixth: Test Your Limits.
I think that most of us spend some time in our early adult life breaking the rules and testing our limits. It is a badge of honor for many to pull your first all-nighter. We all want to know how far we can push ourselves until we break.
The younger you are, the easier this is. After five years, this gets harder. I recall having a few project deadlines with branded partners that all managed to get delayed into one horrible week where everything was due at once. Everyone involved knew that I was a victim of unfortunate events. They were all sympathetic. They all needed their stuff completed and shipping regardless of all of that. I literally spent the whole week alternating between drinking coffee and Pepto Bismol, straight from the bottle. I managed to get through it all in one piece, but I had to take some time to recover.
The older you get, the less likely you can do this. You should know what your limits are at all times. By figuring out what changed from the time you were working all night in college to what it is like five years later, you will realize that the Reaper will be waiting at the blurry edges of your vision more and more often the harder you try to push yourself. Know what you are capable of doing when push comes to shove. You should also know that every time you do push those limits, Mister Reaper likes to sneak closer.
Lesson the seventh: Be Ready To Walk Away
One of the first contracts I ever signed was this twenty page beast that I barely understood. I would like to think that I had a great time working with that publishing company, and I did a lot of very unusual things for them for not very much money. Around that time I also was adding a child to my family. I was nervous as we were coming to the end of a long term contract and I was about to go into economic freefall. I continually brought this up regularly with the publisher during the last month of our agreement, and I was incredibly worried because there was almost no talk about contract extension or renewal.
Around that time, they had a competitor entering the marketplace. A friend of mine was working there and was able to get me an introduction. It was clear that I could give them an edge in shipping content faster, and I nervously entered conversations with them that led to an agreement that was financially twice as generous as the first company. On the one hand I knew they were taking a cheap shot at the incumbent. On the other hand, I have bills to pay.
Finally it came down to the final week of my agreement with the original company. We got on the phone and they laid out an embarrassing lowball offer. I remember being silent because it was a pay cut, for a longer agreement, and I felt pretty horrified considering my wife was expecting.
After a few moments of stunned silence I was asked point blank:
“Look, do you want to be in business with us or not?”
That one sentence and its exasperated delivery haunts me to this day.
I don’t even remember the rest of the conversation, honestly. I don’t think I was angry. I don’t think I said anything significant. I just know I took the competitor’s offer.
I know this angered them more than a little. I learned at that point the value in having a BATNA in hand. If you don’t know what that word means, you should look it up.
Sometimes you will reach a point in your negotiations or conversations with people where the only thing you can do is walk away.
Lesson the eighth: It Never Hurts To Ask For A Meeting
When someone makes an announcement that they are starting a company, or that they are making a significant career change, it does not hurt to ask to meet. Some of the best things that happened to me in my life happened simply because I asked for a meeting.
Do not be afraid to leverage your networks to get an introduction. In my entire career I can only think of one time that I was ever explicitly rebuffed by someone when I asked for an intro.
Yes, that person’s name went down in my little book. No, karma has not caught up with them yet.
Most people are willing to invest forty five minutes to an hour of their time if it makes sense. Sometimes simply asking and providing a reason are all you need for it to make sense.
Lesson the ninth: Do Not Trade Sideways
This is one of those places where I almost want to hashtag some people to offer testimony to this lesson. Almost.
I have observed when I interview people that half of the people interested in a new job are not at all interested in the new job. They are running away from their old job.
If you are going to change jobs, do not run away from it. Bide your time. Find an upgrade. It is out there. You can thank me for it later. If you are running away from your old job, it will catch up with you. Every job will suddenly feel like you need to run away from it and you will treat hard challenges with learned helplessness. Instead of trying to figure out how to battle through your problems, you can take a 10% salary increase, a cooler title, and a new flavor of sparkling water. It can get addicting after a period of time, and then suddenly everyone will look at your resume and all they will see is a hamster spinning in a wheel. I own that resume, and I have looked at other people’s version of that resume in equal measure.
I can assure you it is quite unattractive.
In the first ten years of your career you should be pushing for growth and new responsibilities. I assure that there will always be someone who needs smart people to solve problems who is willing to take a chance on you if you can show them you are intelligent, curious, and ambitious.
Seek these opportunities out. Take them when they present themselves. Please do not trade sideways.
Also, keep in mind this advice is in the second bucket of five-year lessons. There will come a time when you have hit a ceiling in growth and all you can do is trade sideways. The longer you can postpone that day, the better off you will be.
Lesson the tenth: Measure Your Sacrifices
I have five children, and I am the sole financial provider for my family. I always promised my wife that I would keep a roof over our heads, and that we would have solid medical insurance. I have been pretty good about keeping up on that for the entirety of my children’s lives, but not without cost.
I have had to make some terrible decisions to protect my family and to keep those promises to them over the years. Sometimes it involved burning a bridge with someone I really enjoyed working with. Sometimes it involved walking away from an opportunity with a lot of upside.
There are times when that was leveraged against me, where people believed that I would turn tail and sign something or amend an agreement simply because I had no recourse or leverage. I have done my best to have a BATNA in hand for the times that I felt that was about to happen. There is a pattern that repeats itself when people are about to turn ugly. I have also done my best to ensure I knew how far I could stretch myself in the short term to ensure I can crash the cargo-plane of my career and ensure my family lives through it.
Over the years I have been blessed by getting to work with a number of people who have observed some of those sacrifices, and have also observed the mark that those sacrifices have left on me. I know some of them read along regularly. I appreciate that more than I can put into any kind of words.
As you build your career, and possibly build a family alongside it, you will have to make horrible choices along the way. This is not some “woe is me” bullshit. I knew what I was getting myself into. In California, the how-much-is-your-rent speedway is run by a DINK (Dual Income No Kids) pace car. It is relentless, has passive income, and it vacations frequently in Europe.
I have foamed at the mouth elsewhere about the cost of living in California, and the talent diaspora that is becoming more real every day. I am now past the point of feeling any shame when someone asks me why I do not own a house yet. I no longer blink when I point out that twenty years of early-stage innovation without a liquidity event in California have not let me join the monocle-eyed cloud-people club of land-owner weathiness. I knew that when I signed up. I still know it now.
Be prepared for the day when you have to make those sacrifices. Also be aware that not everyone you work with will sympathize with them. Some people will be angry with you for your choices. As circumstances have permitted, I have mended as many of those fences as I could.
Do your best to feel sorry about the situation if they do not understand your sacrifices.
Do your best to avoid them if they bear malice despite understanding your sacrifices.
Stay tuned for part three in two weeks. Next week I am taking a hiatus from baring my soul to you all, in order to publish a second shared article!
Have a great turkey week!
