I’m undertaking a 1000-day reinvention project, blogging here daily to track my progress. In Tuesday Book Club, I share an idea from a book.
Today I’m sharing ideas from one of my favorite books for midlife reinvention, Second Act: What Late Bloomers Can Tell You About Reinventing Your Life by Henry Oliver.
Oliver writes:
Most late bloomers do not plan their success. Many do not know what they are aiming for much of the time. They have to rework their early attempts, re-experiment with their ideas, and persist until they find out what works….
The uncertain and inefficient path often gives late bloomers experiences and understanding they couldn’t have got any other way.
I didn’t plan my career. I studied philosophy and economics in college because those two subjects interested me. After graduating I quickly returned to school to get a master’s in statistics so that I could add more technical skills to my resume. I took a bunch of computer science courses, because I saw in the want ads (in a paper newspaper!) that programmers were in high demand.
I worked in software engineering for about ten years, then stopped out of full-time work when my three children were young. I wrote online, about motherhood and about tech. I wrote a book about using the web to work across distances. I worked as a math teacher at a charter school. I eventually went back to school to get a PhD in statistics.
And then, voilà! I was perfectly prepared to enter data science, with my PhD in hand, my newly refreshed math skills, and my decade-plus as a software engineer.
I prepared for data science inefficiently. But I couldn’t have done it any other way. Data science didn’t exist as a field when I graduated from college.
I spent twelve years in data science before retiring in 2024. I started out with predictive modeling, then added machine learning engineering, and later came to speed on AI (where AI = generative AI, though I think I’ve been doing AI all along). I didn’t plan for that. I was just having some fun and making a living all along.
While many self-help books and articles will urge you to set ambitious goals and make plans to achieve them, in fact, reinvention often benefits from having no goals or objectives at all.
inefficient preparation to be an artist
I’ve wanted to be an artist since I was twelve, or maybe younger. I didn’t get really serious about it until about ten years ago, when I started painting regularly. I now paint almost every day.
I have read books, watched tutorials, and taken classes. The most productive thing I’ve done though is experiment. I’m always trying new things. I’ve learned a lot about what works and what doesn’t, what I like and what I don’t.
If I set out ahead of time and thought, “I’m going to spend ten years turning into the artist I want to be” I never would have done it. But here I am, happy with who I am as an artist, and what I produce. Last year I showed my work in juried shows and sold one piece.
I’m not sure I’ll do much more with my art from now on other than enjoy it myself. Nevertheless, I feel satisfied with where I ended up. No objective or goal necessary!
how to prepare inefficiently
Pick things to do that you intrigue you and inspire you. Don’t have an objective in mind. Just spend time and effort. Bring your attention to the things in life you care about.
Sometimes you pick things because you need to make a living. That’s how I got into programming. But I had also started programming at age twelve, when my dad bought an Apple II computer. I started inefficiently preparing for my job as a software engineer when my sister and I drew a horse in pixels using BASIC.
My daughter is devoted to helping homeless animals. She joined a foster animal organization and began fostering homeless dogs. After a few foster dogs, she took on the role of foster coordinator. She ensures that the volunteers who are fostering dogs have the support they need.
Last year she started pursuing a master’s degree in social work with a certificate in animals and human health. She’s bringing together her love of animals with her professional preparation to become a social worker. She didn’t plan it.
Efficiency is overrated. Knowing exactly what’s next is overrated. If you have the resources, try something that appeals to you, just because it appeals to you.
My inefficient reinvention
I’m not just 309 days into my reinvention, because I started with a year-long project before that. So I’m approaching two years. I started this 1000 day project because I realized one year (or two years) is not enough for a reinvention.
During my reinvention I have: started a YouTube channel, shown my abstract paintings in juried shows (as already mentioned), launched a conceptual art+essay project, joined art groups and volunteered to help them with social media, written a lot about money management, interviewed for jobs at animal shelters, and drafted a nonfiction book about midlife romance and dating.
Where has that gotten me? Not much of anywhere, so far. This reinvention process has been extremely inefficient.
My latest activity is focused on trading and investing, with the plan to focus on that as my main professional-ish activity. I’m exploring trading strategies like the triple income strategy / options wheel. I started an investing newsletter and wrote on it a few times. Of all the things I’ve done, that’s what I keep coming back to. But I don’t have any goal around it at this point, other than to arrive at a money management approach that will serve me through what could be four more decades of retirement.
Keep trying & accept incompetence at the beginning
Oliver shares that it’s important to keep trying, which will bring more failure, but also more success:
People who keep trying have more successes (as well as more failures) than people who stop. This has been detailed and described for decades by psychologists like Dean Keith Simonton….
The ‘constant probability of success’ theory says that the more attempts you make to hit a target, the more bullseyes you actually will make.
Inefficient doesn’t mean lazy. It doesn’t mean working less or working without passion. All along I’ve thrown myself into whatever I’m doing. My latest fascination with trading and investing is no different. I watch videos, check books out from the library to learn more, attempt different approaches (with real money, not just paper money), analyze what works and what doesn’t.
As much as I’d like everything I do to work out immediately, it doesn’t. Expertise is developed through constantly learning new things and then applying them. It necessarily starts from a place of little to no expertise.
Oliver writes:
Something that doesn’t go well at first might be your best option in the long run. This is true of choosing what projects to prioritize, what technologies to invest in, and what career path to follow. Doing something you are comparatively less good at in the short run might not seem like the best idea, but it can be. Not knowing what sort of practice will pay off is one of the biggest challenges we face when making these decisions….
We should aim to be comfortable at being incompetent when we try new things. The more we branch out, the more we can discover what we are really good at. We had to be incompetent for a long time while we developed our current expertise, and sometimes we should be willing to be incompetent again.
I do feel extremely incompetent with trading and investing right now. Had I just thrown all my money into an S&P 500 index fund I’d have a lot more of it right now. But I wouldn’t have learned so many things about the world and I might not be able to manage my money so well for the next decades.