Starting Over... Again

I am starting over again.

I’ve done this before.

It’s harder this time.

Yet this time I believe it is even more necessary.

My career was in finance. I loved the markets, specifically the math and psychology of it. I read hundreds of books and development thousands of models for everything from micro-market trading strategies, to macro-economic risks on globally invested portfolios. I helped firms understand and measure political risk, allocate client portfolios based on quantitative strategies, and attempt to obtain decent returns with less risk. I kept hundreds of Ned-Davis-type charts. I still have many of the files and simulations I did for various jobs and types of clients. I had an entire room in my apartment for all the books I had read and used for reference. Some were economic theory books from the 1960s, others were quantitive write-ups on money market funds, still, others were memoirs of firms or events. Nothing was too boring, and everything further added to my view and how I approached various problems.

Yet for all the knowledge and ability I had gained, it was 2012. The last few years of trying to work in a consolidating industry (one that would most likely continue to consolidate for my entire working career) left me worn out and running in place. No matter how much I worked, the reality was that there were always going to be smarter, more connected people than me in the field. I finally came to the realization that I could extend the same effort in another vertical and achieve outsized returns. This was attractive given my risk-based approach to finance. I would now use it towards my career.

I started working at a small fastener distributor and quickly found I could apply many of the concepts of risk and return to building a business rather than analyzing one. I could even turn loose my mathematical joy on many difficult supply chain problems. I soon started a supply chain business on the side. The business grew, and so did my confidence in selling, operating, and figuring things out. I started another company in Mexico doing similar work. I learned a new language, two sets of tax laws, and two business cultures. I built businesses in two countries simultaneously. I learned new industries, gained certifications, and gave it the same intensity I had given finance before.

But even in the early part of the supply chain career, I could see something happening in many other industries that would soon make me and my business a relic. Software. So I started learning to code. I went to meet-ups. I made applications. I wrote programs to automate ordering and demand planning, to give us real-time insight on usage at customer facilities, to track suppliers and their information, to create inspection plans, and more. I automated many tasks and created software to do the rest in a small amount of time.

However, these skills were also gaining in irrelevance. The problem was not being able to write software, or create a complex supply chain, but to be able to scale this at 10x or 100x; complexity and size. For this, I needed to understand machine learning, deep learning, and the tools that are being used to implement them. So I started new programming languages, new courses in math, and started to apply them to current problems of inventory optimization, part classification, supplier clustering, and various other tools of quant.

And here I am today, starting over. It’s harder because I have a family. It’s harder because I am older. These decisions get harder because we get comfortable and confident where we are. Leaving that space means we don’t know what, we don’t know how… we don’t even know if. I don’t know if. Can I make it in a new industry? In a new environment? Am I too old? Too amateur? Too small-time for the giants I read about?

I don’t know the answer to any of those questions. I do know that I also think about what if? What if I step out and this ends up being fulfilling to me, my family, and the clients I work with? What if I help solve real problems and continue to grow myself at the same time. What if I don’t? How will I feel in ten years? Regret? Remorse? Like I wasted my time or gave up? I’d rather try and fail then have that.

I don’t know the answer to any of those questions, but I am willing to find out.