Appreciate this, Todd. I’m 38, and while I’m not in crisis mode, a lot of what you said resonates,especially that weird tension between feeling like you’ve still got time and knowing that, realistically, time is moving fast.
I’ve been divorced a few years and have rebuilt a solid, fulfilling life, but that doesn’t mean I’m not thinking about long-term strategy,especially as career momentum shifts, parents age, and financial priorities evolve. It’s not about panic. It’s about being smart.
The part about avoiding “get-rich-quick” traps is spot on. I’ve seen too many friends waste time chasing shortcuts instead of building stability. And yes to hiring the right professionals,there’s no award for doing your taxes or insurance planning alone.
I’d be curious to hear your thoughts on mid-life investing when you’re self-employed and not aiming for some corporate ladder outcome. The whole “just max your 401k” advice doesn’t really fit for a lot of us.
Thanks for reading and sharing your thoughtful comments.
In terms of mid-life investing when self-employed, you're correct that the standard just "max out your 401k" advice is insufficient. Being self-employed, you likely have more short-term liquidity risks than the salaried W-2 employee. Income is more variable when you're self-employed, in good and bad ways.
As such, I would think about what cash savings you might need to get through a tough six month period and focus there before prioritizing longer-term savings. Having that bedrock of short-term savings will provide peace of mind that you can get through short-term challenges without having to raid your long-term investments (which are best held patiently).
Your cash savings don't have to be kept in checking earning zero interest, either. There are bank savings accounts, money markets, CDs, etc. that can generate enough interest to offset most, if not all, of inflation's negative effects.
If you're self-employed, I'd encourage you to research Solo 401ks, as well, as these can be good vehicles for adding additional funds to your retirement savings once you have a comfortable savings base.
Hope this helps. This is for informational purposes rather than personalized advice.
That distinction between short-term liquidity and long-term investing is something I’ve had to learn the hard way,especially after going through the ups and downs of self-employment. I used to feel guilty for keeping too much in cash, but like you said, when income isn't predictable, optionality really matters.
I’m looking into Solo 401ks now. One thing I’ve noticed, though, is that financial advice often assumes a linear income path or a clear “scaling up” model, which doesn’t always apply when your work evolves more like a portfolio of projects than a single business track.
Yes, if you think about it from a writer's/publisher's POV, the largest audience is salaried employees and circumstances for self-employment can be variant and niche, making it difficult to appeal to a wide enough audience to give general advice, sell books, etc.
When I analyze businesses with lumpy, cyclical, or seasonal income patterns, I find it helpful to "normalize" results, or assume the mid-cycle as my starting point for any projections. The worst thing you can do from a personal finance standpoint is assume that a particularly good year is the new baseline. It's much harder to scale back than it is to scale up. But you also don't want to be too gloomy as you'll be too conservative. Finding an average of the peaks and valleys is usually a good place to start.
I’ve been learning the hard way not to treat a strong year as a new baseline. After riding a few good waves followed by some quieter stretches, I’m starting to see the value of planning around the middle ground instead of the highs.
What I still struggle with is finding the right mindset when numbers say to average things out but emotionally I feel cautious. Even in a good year, I hesitate to make big moves like bringing someone on board or committing to long-term projects. Do you usually go by the numbers alone in those moments, or do you have a way of checking in with your own instincts too?
Hi Todd, thank you for the post! Can you share a bit about how earning your CFA allowed you to teach college level finance? Was this at a University? As a current level II candidate this is an exciting prospect as I have always wanted to teach a college course part time at some point.
Hi Zach, It depends on the institution and the accreditation requirements, but generally speaking, if you have a CFA, you can be an undergraduate/graduate adjunct and/or a full-time undergraduate lecturer (lecturer is a different track than academic). Having the CFA plus industry experience helps in all regards. I would encourage you to explore teaching, as I've found it invaluable.
Hitting 40 was such a weird age for me. I was young enough to remember my blissful ignorance of youth and a time before my body started to require more dedicated effort to stay fit. Yet I had some battle skars and real life experience by 40. At times I felt so much more mature than just 10-15 years prior. Although 20-25 year old me thought I would be so much smarter by age 40. lol.
Agreed! I don't think my 20 year old self would have expected to have the life experiences that I had the subsequent 20 years. Some good, some bad. I'm probably short of the knowledge I expected to have by now, but further along in wisdom. Hopefully!
Great piece Todd, like you say 40s is a fraught time. For a lot of people it is likely the first time they are accumulating some real assets, and at the same time accumulating more dependencies and responsibilities. Feels like what Jay Powell said, navigating by the stars under cloudy skies.
To seed, build, and nurture timeless, intangible human capitals — such as resilience, trust, evolution, fulfilment, quality, peace, patience, discipline, relationships and conviction — in order to elevate human judgment, deepen relationships, and restore sacred trusteeship and stewardship of long-term firm value across generations.
A refreshing poetic take on our business world and capitalism.
A reflection on why today’s capital architectures—PE, VC, Hedge funds, SPAC, Alt funds, Rollups—mostly fail to build and nuture what time can trust.
Built to Be Left.
A quiet anatomy of extraction, abandonment, and the collapse of stewardship.
"Principal-Agent Risk is not a flaw in the system.
Appreciate this, Todd. I’m 38, and while I’m not in crisis mode, a lot of what you said resonates,especially that weird tension between feeling like you’ve still got time and knowing that, realistically, time is moving fast.
I’ve been divorced a few years and have rebuilt a solid, fulfilling life, but that doesn’t mean I’m not thinking about long-term strategy,especially as career momentum shifts, parents age, and financial priorities evolve. It’s not about panic. It’s about being smart.
The part about avoiding “get-rich-quick” traps is spot on. I’ve seen too many friends waste time chasing shortcuts instead of building stability. And yes to hiring the right professionals,there’s no award for doing your taxes or insurance planning alone.
I’d be curious to hear your thoughts on mid-life investing when you’re self-employed and not aiming for some corporate ladder outcome. The whole “just max your 401k” advice doesn’t really fit for a lot of us.
Hi Blanca,
Thanks for reading and sharing your thoughtful comments.
In terms of mid-life investing when self-employed, you're correct that the standard just "max out your 401k" advice is insufficient. Being self-employed, you likely have more short-term liquidity risks than the salaried W-2 employee. Income is more variable when you're self-employed, in good and bad ways.
As such, I would think about what cash savings you might need to get through a tough six month period and focus there before prioritizing longer-term savings. Having that bedrock of short-term savings will provide peace of mind that you can get through short-term challenges without having to raid your long-term investments (which are best held patiently).
Your cash savings don't have to be kept in checking earning zero interest, either. There are bank savings accounts, money markets, CDs, etc. that can generate enough interest to offset most, if not all, of inflation's negative effects.
If you're self-employed, I'd encourage you to research Solo 401ks, as well, as these can be good vehicles for adding additional funds to your retirement savings once you have a comfortable savings base.
Hope this helps. This is for informational purposes rather than personalized advice.
- Todd
That distinction between short-term liquidity and long-term investing is something I’ve had to learn the hard way,especially after going through the ups and downs of self-employment. I used to feel guilty for keeping too much in cash, but like you said, when income isn't predictable, optionality really matters.
I’m looking into Solo 401ks now. One thing I’ve noticed, though, is that financial advice often assumes a linear income path or a clear “scaling up” model, which doesn’t always apply when your work evolves more like a portfolio of projects than a single business track.
Yes, if you think about it from a writer's/publisher's POV, the largest audience is salaried employees and circumstances for self-employment can be variant and niche, making it difficult to appeal to a wide enough audience to give general advice, sell books, etc.
When I analyze businesses with lumpy, cyclical, or seasonal income patterns, I find it helpful to "normalize" results, or assume the mid-cycle as my starting point for any projections. The worst thing you can do from a personal finance standpoint is assume that a particularly good year is the new baseline. It's much harder to scale back than it is to scale up. But you also don't want to be too gloomy as you'll be too conservative. Finding an average of the peaks and valleys is usually a good place to start.
I’ve been learning the hard way not to treat a strong year as a new baseline. After riding a few good waves followed by some quieter stretches, I’m starting to see the value of planning around the middle ground instead of the highs.
What I still struggle with is finding the right mindset when numbers say to average things out but emotionally I feel cautious. Even in a good year, I hesitate to make big moves like bringing someone on board or committing to long-term projects. Do you usually go by the numbers alone in those moments, or do you have a way of checking in with your own instincts too?
Hi Todd, thank you for the post! Can you share a bit about how earning your CFA allowed you to teach college level finance? Was this at a University? As a current level II candidate this is an exciting prospect as I have always wanted to teach a college course part time at some point.
Hi Zach, It depends on the institution and the accreditation requirements, but generally speaking, if you have a CFA, you can be an undergraduate/graduate adjunct and/or a full-time undergraduate lecturer (lecturer is a different track than academic). Having the CFA plus industry experience helps in all regards. I would encourage you to explore teaching, as I've found it invaluable.
Thanks for the bonus eighth tip!
Hitting 40 was such a weird age for me. I was young enough to remember my blissful ignorance of youth and a time before my body started to require more dedicated effort to stay fit. Yet I had some battle skars and real life experience by 40. At times I felt so much more mature than just 10-15 years prior. Although 20-25 year old me thought I would be so much smarter by age 40. lol.
Great post.
Agreed! I don't think my 20 year old self would have expected to have the life experiences that I had the subsequent 20 years. Some good, some bad. I'm probably short of the knowledge I expected to have by now, but further along in wisdom. Hopefully!
Great piece Todd, like you say 40s is a fraught time. For a lot of people it is likely the first time they are accumulating some real assets, and at the same time accumulating more dependencies and responsibilities. Feels like what Jay Powell said, navigating by the stars under cloudy skies.
Hello there,
Huge Respect for your work!
New here. No readers Yet.
But the work has waited long to be spoken.
Its truths have roots older than this platform.
My Sub-stack Purpose
To seed, build, and nurture timeless, intangible human capitals — such as resilience, trust, evolution, fulfilment, quality, peace, patience, discipline, relationships and conviction — in order to elevate human judgment, deepen relationships, and restore sacred trusteeship and stewardship of long-term firm value across generations.
A refreshing poetic take on our business world and capitalism.
A reflection on why today’s capital architectures—PE, VC, Hedge funds, SPAC, Alt funds, Rollups—mostly fail to build and nuture what time can trust.
Built to Be Left.
A quiet anatomy of extraction, abandonment, and the collapse of stewardship.
"Principal-Agent Risk is not a flaw in the system.
It is the system’s operating principle”
Experience first. Return if it speaks to you.
- The Silent Treasury
https://tinyurl.com/48m97w5e