While thinking about how to write this post, I figured the best way to do so would be through an analogy, specifically, a measuring stick. If I were to go ahead and measure where I am in my career, it really needs to be done using the correct measuring stick. If you use one that is the wrong unit or the wrong scale, then obviously you are going to come up short. But use one which is calibrated properly and everything will come out just right. I therefore propose three scales against which I will measure my career at this stage in life and then readers can use them to measure where they are at any given point in time.
The Childhood Dream: President of the United States

Yes, yes, this is a terrible measuring stick to use, but I think it can still lend some perspective that dreaming big is never something to be ashamed of. Now I’m not saying that as a 5 or 6-year-old that I would respond “President of the United States” instead of your standard “fireman” or “teacher” if asked what I wanted to be when I grew up. I guess it was more of a dream than anything else. The source of this dream was probably because my brothers would take the sports section of the newspaper during breakfast, leaving me with the front page or metro sections. So I pretty quickly became fascinated with world and local events. These were the heydays of Clinton and Mayor Menino and the Big Dig, and as such, my fascination with public works projects and national issues continues to this day.
Needless to say, I am not the President of the United States, and I’m not really sure I would want to be either. It mostly sounds like no fun at all, being that you need to constantly be in a security bubble. So instead I enjoy reading about presidents and their lives, from the inner workings of the White House, to Air Force One, or even the nitty-gritty of running a presidential campaign (I will finish What It Takes one day, but this book has possibly the most gripping intro to a non-fiction book I have ever read). Also, living in Israel, I no longer qualify to be president, unless I first move back for 12 years, which would be quite disruptive to my family with no guarantee of actually being president. However, it only takes around NIS 30,000 to start a political party in Israel…
I Do It for My Family: Can you support your family?
I would say another measuring stick to use in judging your career trajectory and progress is whether or not you are able to support your family with your current job. This can be in many areas, from financial, to work-life balance, etc. And this doesn’t mean without the support of a second income. If you and your spouse are able to support the lifestyle that you want, and that lifestyle is not overly extravagant, then consider yourself successful. If this is the measuring stick we are using, then I too am measuring as far as it goes, if not a little bit more.
What if you’re not? Then there are a lot of things you can do. Probably the most obvious thing to do is to go look for a new job. Have you outgrown your current responsibilities? Is going to work burdensome? Then it may be time to start looking. Another thing you can do is try and learn a new skill. This can aid in either changing your field of work, or beginning a side-hustle, which leads me to my next suggestion?
What if you like your work, and you’re on a good path but it still isn’t enough each month? This is where a side hustle comes in handy. And it is more common than you think, and there are more of them out there than you think. First, consider any hobbies you may have and see if you are able to create a product from any of them. This way you are able to have fun and make money at the same time. Find customers in your synagogue or church. If you don’t have any marketable hobbies, then start learning something new, or do some Google searches or ChatGPT conversations to get an idea of what might work. I just found this YouTuber who deals in abandoned freight and then sells what he bought (at rock-bottom prices) on eBay and Facebook marketplace. Try to avoid the “content-creation” game. It is often time-intensive and the market is super saturated. I just blog mostly for fun and throw in a couple of affiliate links here and there, but I don’t expect to be hitting the blogging jackpot anytime soon, if ever.
Societal Impact: Is your work making an impact on society?
Another way to measure your job when it comes to a milestone age is whether or not your job is making a difference in the world. This does not need to be objective. In other words, even if you’re not Mother Theresa, you can still be fine. You can even be doing something that most of the world does not see as impactful but which you have justified as being worthy. For example, you may be some investment broker whose job is to make as much money as possible, no matter the cost (though always legally). People may say that “there is more to life than money”, but if you view it as you are allowing other people to retire comfortably or to give their children better lives, then while you may be making exorbitant amounts of money and working 26 hours a day (not a typo), if that is what brings you joy, then that’s totally fine. Just always keep it legal, please, going to jail is a great way to fail at the second measuring stick (and this one too).
Thankfully, in my case, I am able to make an impact in many areas. My job helps bring computers and medicine together so that we can discover new drugs and make people healthy again. If your job is at the intersection of the things you like and also making the world a better place, then mark yourself down as measuring up to where you should be at this stage of life.
Other bits
There is actually a ton of job and career advancing knowledge out on the internet, and there is always more to learn. For example, did you know that having a career is not always about climbing the corporate ladder and trying to go as high as you can? Like honestly, not everyone can be a manager (just like every doctor can’t have been a straight-A student). For those of us not on the corporate ladder climb, there is a separate track, and it is called “Individual Contributor”. I just learned about this a few months ago. Go look it up more if you aren’t familiar with it.
Sign up for newsletters and email lists in your field. I get TLDR every day (sign up so I can get swag!), which has a great mix of tech headlines, but also includes a lot of good career advice (mostly focused on the tech sector, but not always).
People also swear by networking, but I have never once found a job through networking. It has always been through cold applications on LinkedIn or corporate websites. Your mileage may vary, and it certainly can’t hurt, I just wouldn’t worry too much if you don’t have a huge network. As your career moves along you’ll meet plenty of people and you’ll learn that most likely your field is pretty small so you’ll have a mini-network by default. Also, again, your religious institution is a great network, at the very least is a group of people who might be able to make referrals should you ever need them.
What other measuring sticks are there for career progress and achievement that I didn’t mention? Where are you on your measuring stick? Leave a comment below (and be the first commenter on the blog!).
Buy some stickers!