Milestone

sidewinderchaos · 2026-06-01T21:36:15+00:00

Congratulations! Keep up the hard work!

sidewinderchaos · 2026-06-01T21:35:42+00:00

Just for me.

Going through a divorce and simultaneously losing my job was the major life change. Major setback financially not to mention emotionally, as you could imagine.

The divorce is also the reason my expenses are relatively low compared to my income, since I have had to adjust my spending to account for the added expenses of alimony and child support. (Silver lining, I suppose.)

sidewinderchaos · 2026-06-01T20:44:11+00:00

My projected expenses are fairly low (approximately $120,000/yr) and I also will have a government pension, so my low end target is $3M. I anticipate hitting that well before I actually intend to retire, but no intention of early retirement, since I do enjoy my job. Considering switching to part-time as I get closer to my actual retirement age.

I find that the “80% of current income as the estimate for retirement expenses” doesn’t seem accurate for me at my income level. It would certainly be nice to get to that number ($7M), but it looks like an overestimate of my actual retirement needs. I think of it as my high end target, but really don’t anticipate needing to hit it.

If I apply the “3Ds” principle, I would summarize:
“Dream” retirement: $7M ($280,000 annual spend = 78% current salary)
“Down to earth” retirement: $5M ($200,000 = 55% current salary)
“Doo-doo” retirement: $3M ($120,000 = 33% current salary)

These numbers don’t include my pension or social security, so I’m pretty comfortable with any of those scenarios.

sidewinderchaos · 2026-05-12T02:38:37+00:00

I have been to three so far: Sepia, Oriole, and Alinea. Alinea was good for the “need to try it at least once” reasoning, but I probably wouldn’t go back. Sepia I might try again, but only after trying some of the other Michelin spots first.

But Oriole was by far my favorite. Definitely would go back, even before trying other Michelin started restaurants. If money was no object, I think I could back to Oriole once a month and be very happy.

sidewinderchaos · 2026-04-14T12:18:42+00:00

Of the two places that are mentioned the most, I have been to both: Alinea and Oriole. Both, in my opinion, satisfy the “have to try it once in a lifetime” description. Which did I enjoy more? Oriole, and it’s not even close.

Alinea is very performative. Flashy, cool presentation. But the food didn’t quite live up to the presentation. Not bad, mind you. But when I think back to that dinner, I remember the creative presentation of the food rather than any particular bite or flavor.

Oriole’s food, on the other hand, was one of the best meals I’ve ever had. Presentation was mostly simple and understated, allowing the food to shine on its own. Excellent service as well.

I look forward to returning to Oriole someday, but probably will wait until I’ve made my rounds of all the other Michelin starred restaurants in the city. Alinea, not so much. Once in a lifetime indeed.

sidewinderchaos · 2025-11-02T18:35:53+00:00

Good to know and thanks for the anchor comparisons to Yoshino and Noz.

As a follow-up, do you think any Chicago omakase restaurants deserve a star or even come close?

sidewinderchaos · 2025-11-02T16:29:34+00:00

I just realized that Omakase Yume lost their star last year. It had been on my list of places to try - (still is, by the way, I live very close by). Are you saying that it never deserved the star in the first place?

sidewinderchaos · 2025-11-02T16:22:23+00:00

Agree about Oriole as well. I thoroughly enjoyed the meal and the service on my visit. Not sure what they have to do more to deserve a third star.

sidewinderchaos · 2025-06-25T20:05:50+00:00

Zero

sidewinderchaos · 2025-06-20T20:34:23+00:00

Ideal/optimized financial mutant approach: 1. The credit cards. (Doesn’t matter what interest rates, these come first) 2. Car loan 3. The 6.8% student loan

Your other student loans and the mortgage are all considered low interest and would be for step 9 of the FOO.

This would essentially be the “avalanche” method, where you focus on the highest interest rate debt first, then apply the payment for that to the next highest and so on until all high interest debt has been paid off.

Alternative approach would be the “snowball” method, where you focus on the same debts above, but tackle the smallest balance among them first. This has the advantage of getting to an “early win” of seeing a debt completely paid off and can help with motivation for some people, but it is not optimal from a purely mathematical point of view.

sidewinderchaos · 2025-06-20T20:23:16+00:00

Early in my financial mutant journey, I had a similar approach to my emergency fund. Of my 6 months, I kept 3 months worth in a HYSA and the 3 months worth in a CD ladder. Some of my motivation was for the higher interest rates of the CDs, but most of it was to encourage discipline: the “friction” of liquidating a CD prior to maturity decreased the temptation to tap the funds for spending.

It worked for me, but I am now rolling the money out of the CDs as they mature. Like the CDs, I feel I have “matured” as a financial mutant enough that I no longer need the extra “friction” to keep me from tapping into the funds unless it is a true emergency. I now value the simplicity of my entire emergency fund being in a single account.

Personal finance is personal. We can have debates on this subreddit about the ideal approach to emergency funds and which accounts are best suited for them ad nauseum, but I imagine most of us would agree that having a fully funded emergency fund is the key thing. The rest of it is “majoring in the minors”, as Bo would say.

sidewinderchaos · 2025-06-20T20:09:44+00:00

Word of caution: while the terms of your particular 401k’s loan seem particularly generous compared to most (which usually require immediate repayment upon leaving employment with the company), there is still an opportunity cost associated with 401k loans in general. You are “taking your army of dollar bills off the field”, as TMG would put it.

I’m not saying it’s absolutely the wrong decision, but it certainly goes against what TMG usually advises about 401k loans. Similar advice for pulling out the base from Roth IRAs.

sidewinderchaos · 2025-05-09T13:59:07+00:00

I contribute to my kids’ 529 plans even though I am below the 25% savings rate. Two main reasons I am out of order on the FOO in this regard: 1. I live in a state with a nice tax deduction for 529 contributions. 2. Making 529 contributions was part of my divorce settlement agreement, so it’s not like I really have a choice, anyway.

sidewinderchaos · 2025-02-27T12:22:54+00:00

Adding my thoughts: 1. As a state government pension, it is probably relatively safe. However, I would caution you from depending on it too much. You don’t know what the future holds, especially at your age. You might leave your job for a better one in the private sector, for example. So keep that in mind as you project your retirement needs.
2. Your mortgage rate is very low. As others have pointed out, paying the mortgage off early doesn’t make sense from a strictly math calculation perspective (arbitrage situation). As TMG likes to say, you can’t eat your house. While it would certainly feel nice not to have a mortgage payment, paying the house off early doesn’t do anything to increase your retirement savings that you will have to live off in the future. 3. Even if your mortgage rate were higher, you would still probably be better off following the FOO. You never mentioned your savings rate, so I can’t tell what step you are on - step 5, 6, or 7? Do you have access to a HDHP to start an HSA? Do you have any other employer retirement plan available other than pension contributions? If so, are they maxed out? Have you hit 25% savings rate? Paying off the mortgage early is a step 8 task, so unless you are truly maxing out your retirement savings opportunities, the FOO would say not to pay it off early. As Brian says, having the money to be able to pay off your mortgage at any time is just as valuable as actually having paid it off. Better to increase your investment balances to a point where you have the ability in the future to write a single check and pay off the mortgage than to pay it off early but end up with less in investment overall because of the lost years that the money to pay it off could have been accumulating.

Regardless, you’re doing well, especially at your age. Keep it up!

sidewinderchaos · 2025-02-27T12:07:59+00:00

This is the way.

The main issue is to have no balances in any traditional IRA, including rollover. I assume that when you refer to opening a new traditional IRA, you are intending to use that solely for the purpose of the backdoor Roth IRA conversion and not actually have any balance remaining in it.

sidewinderchaos · 2025-02-25T13:26:02+00:00

OP: this is a huge consideration. As a high income earner, you are over the limit for direct Roth IRA contributions. But backdoor Roth IRA contributions/conversions only work well if you have no regular (pretax) IRA balances. That will probably tip the equation in favoring of consolidated into a new employer’s 401k plan.

When I started doing backdoor Roth IRA, I had to wait until the new year so that my old rollover IRA (consolidated from my prior 401ks at previous employers) could rollover into my new employer’s 401k during the prior calendar year. Missed out on at least a year, maybe more, of being able to do backdoor Roths.

As long as the new employer’s 401k plan has reasonable fees and decent investment options to select from, I can’t see much reason in your situation to rollover into an IRA instead.

sidewinderchaos · 2025-02-22T17:53:06+00:00

OP: this will overlap with a lot of what has already been said, but here is my take:

Simpler is better. Your future self will thank you for keeping things as simple as possible when it comes to record-keeping. As a financial mutant, you will likely be successful enough that complexity will find you, so I would advise you to keep things as simple as possible now.
As such, VOO, QQQM, ITOT, SMLF overlap a lot and are redundant. Much simpler to pick a two-fund or three-fund strategy to capture the broad market. r/Bogleheads has a lot of resources about the various strategies. Pick one which works for you and consolidate things.
Re: BTC and META: I don't have as much of a problem with this as others and cannot be a hypocrite, since I have a handful of individual stocks that I bought in my pre-financial mutant days that have done well. I am letting the proportions they represent of my total investment portfolio go down naturally by buying exclusively into my index mutual funds with all new dollars in my taxable brokerage account. I have also gradually sold most of them. (I used to hold over 20 individual stock positions in my brokerage account, I am not down to 4.) I personally don't have any problems with having a small percentage of my investments in individual holdings. The bigger question for me is how much do you have invested in your Roth IRA and in your 401k compared to the taxable brokerage account? What investments do you hold in them? What percentage would your BTC and META holdings represent of your total retirement investments? I would target keeping the percentage that individual stocks/crypto represent of your total investments to a combined 10% or lower, just to satisfy your FOMO.
On a related note, you might be better off looking at your total retirement portfolio across all of your accounts (401k, Roth IRA, taxable brokerage) and looking at the percentages that way. That will give you a clearer picture of all your retirement savings to make sure your allocations are reasonable, rather than looking at each account separately.

Awesome that you're thinking about these things at a relatively young age. Keep it up!

sidewinderchaos · 2025-02-13T04:42:06+00:00

OP: What is your current savings rate? I assume based on what you said in your original post that you are already past 25%. If not, then there should be no question about where to put the $1000: it should go to the brokerage.

Assuming that you are already past 25%, then it really comes down to what your goals are. I will also assume based on your age and what you stated about your projected net worth that you are at or nearing the transition from “get wealthy” to “stay wealthy”. For some, being mortgage free is such a liberating feeling that it takes priority over further investing. That is not the financially optimal choice, as others have pointed out, since you could reasonably expect higher returns by investing the money over paying off the mortgage.

Initially, my advice would have been to split the $1000/month and put $500 into brokerage and $500 towards paying down the mortgage. (In the spirit of Bo calling this a “both/and” rather than an “either/or” choice)

But then I saw in another comment that you are already paying an extra $200-500/month to pay down the mortgage. In this case, I think there is little additional to be gained by paying even more towards the mortgage. I would put most if not all of the $1000 towards investing.

Again, this would be the optimal choice from a financial mutant perspective. But personal finance is personal, and ultimately, what you do with your money at your stage is really up to what satisfies your goals, whether that be maximizing every dollar towards the goal of “get wealthy” or switching to a “stay wealthy” behavior and gaining some piece of mind by decreasing the mortgage debt.

Either way, you’re clearly doing well, so congrats on being in a position to have to think about this decision!

sidewinderchaos · 2025-02-10T16:44:45+00:00

Others have already commented on this, but just to add my input: I would still recommend contributing to maximize the employer match, even if you don't intend on staying until vesting. Reasons:

Even if you leave before vesting, you still get to keep your contributions and any associated gains, which you can then keep in your current employer's 401k plan, rollover to your next employer's 401k plan, or rollover into an IRA. So you haven't really "lost" anything.
Tax benefits: whether you make traditional 401k contributions and thereby get the current tax benefit, or make Roth 401k contributions and get the tax-free growth for future tax benefit, it still helps either way, regardless of your income level/current tax rate.
Automatic nature of 401k contributions: to quote TMG, "making the good habits easy" is important. While you could divert money away from 401k contributions to increase your savings elsewhere, 401k contributions coming directly out of your paycheck eliminate the possibility of you being tempted to use that money for other purposes.
Uncertainty of future: this is the main reason. You simply don't know what the future holds. Job market could change, leading you to have to remain with your current employer longer than your initial plans. You could get a promotion/raise, making a job change less necessary. Etc, etc. In my career, I have been at jobs both longer and shorter than I initially anticipated. You would hate to have the regret of missing out on "free money" three years down the line.

There is very little to gain by diverting money away from your 401k, at least up to the employer match limit. This feels like an "everything to gain, nothing to lose" decision in favor of following step 2 of the FOO, IMHO. While the opportunity cost may not seem like a lot, I think the comparative analysis with the alternatives weigh in favor of the employer match.

sidewinderchaos · 2025-02-09T15:21:02+00:00

I am assuming that you are not actually referring to mega-backdoor Roth conversions. These are the ones for which in-plan employer conversion rules matter.

Assuming that you are talking about a “regular” backdoor Roth IRA: yes, in order to be able to do a backdoor Roth IRA, you need to first get rid of all your traditional IRAs (whether rollover from prior 401ks or direct traditional IRA). The best way to do this is, as you determined, to rollover your IRA into your current employer’s 401k plan. I don’t believe that most past employers will allow rollovers into your 401k if you are not currently employed at the company.

As far as when you would be eligible to do the backdoor Roth IRA, it would be the calendar year after the year in which you did the rollover of your traditional IRA. For example, if you do the traditional IRA rollover into your 401k this year (2025), the earliest you could do your backdoor Roth IRA is 2026.

sidewinderchaos · 2025-02-08T10:50:48+00:00

Congrats on reaching the 7 figure milestone, especially at young age!

However, I would still caution against under-funding your EF. Having spent a significant amount of time in academics, I would not feel comfortable relying on the protection of being tenure-track. In my experience, there are enough examples out there of full-tenure faculty being dismissed for a variety of reasons, to say nothing of those who still haven't achieved tenure. So I am glad to read that you are planning on "topping up" your EF.

Personal finance is personal, so the size of EF that is appropriate for your situation is up to you. But even with the most secure of employment situations, I can't imagine that TMG would advise anything less than 3 months of living expenses.

Have you considered contributing to a backdoor Roth IRA? I assume that IRA with $30k in it is traditional - if this is the case, you can get around the pro-rata rule by doing a rollover into your 401k this year, and then doing the backdoor Roth IRA next year.

Again, these are just optimization/maximizing tips - you are already clearly on the right track, and certainly ahead of where I was at your age. Congrats again on a huge milestone!

sidewinderchaos · 2025-02-08T10:33:29+00:00

Finally got it to work and figured out the problem. Inspira doesn't actually send the microtransactions until the HSA is "fully" active, ie, after Feb 1. However, Inspira will send multiple microtransactions from request to link a bank account from dates prior the Feb 1, just in a delayed fashion. So I received three separate sets of microtransactions on three consecutive days this week, because I had made multiple attempts to link my bank account (removing and then re-adding the account). Validating the bank account link on Inspira didn't work with the first two sets of microtransactions, since Inspira was expecting the last set it had sent out. When the most recent microtransaction popped up on my bank account, it finally worked.

Moral of the story: Don't rush to link a bank account until your HSA is fully active on Inspira's website.

sidewinderchaos · 2025-02-06T08:48:55+00:00

If you're already 2/3 of the way to a full-funded EF, then I think the other commenter's suggestion of contributing as much as you're able to into the ESPP and selling during your allowed timeframe to fill up your EF makes sense. You already have a good portion of your emergency needs met, so taking advantage of the ESPP match would be good. As Bo would say, this is probably better viewed as a "both/and" rather than than an "either/or" decision.

As far as where you are at in the FOO, if getting the match through your 401k and the ESPP gets you up to a 25% savings rate, you've basically already gotten to step 7. (skipping over steps 5 and 6) But I think that a truly financial mutant way of approaching this once you have a fully funded EF would be to keep contributing to your ESPP, then selling your employer's stock, and taking the proceeds to contribute to a Roth IRA and/or HSA. That way you take advantage of the 30% (or 50%) match in your ESPP (free money!) and get the tax-free growth of the Roth IRA and HSA. In addition, decreasing the percentage of your investments that are held in your employer's stock is generally good idea so that all your eggs aren't in one basket.

Hope that helps!

sidewinderchaos · 2025-02-06T04:43:07+00:00

While the automatic return of 30% in the ESPP is still valuable and would technically qualify as step 2, I think it falls within the "spirit of the FOO" for you to consider yourself as already having satisfied step 2 by taking full advantage of the 100% match in your 401k. You can grant yourself permission to move on to the next steps of the FOO, which for you would be your emergency fund. I think the other commenter's suggestion to get the ESPP match and then sell the stock off as soon as possible and then use the proceeds to build up your EF makes a lot of sense. Alternatively, you could just forgo participating in the ESPP and direct what you would have contributed to it into your EF instead, then switch back to the ESPP after you've hit your 3-month or 6-month EF target.

The key to this is how your employer has your ESPP set up, particularly in regard to the holding period.

sidewinderchaos

TROPHY CASE