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How much $ to retire and how to fund your lifestyle in retirement

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I think is time for an update with SP mooning retirement is calling me bad. I am really considering quitting my job because I am not really enjoying it right now and I even got promoted the other day lol. My investments are now 3.5M and I have been selling my stock slowly. I have around 900k in cash and most of my shares are underwater with covered calls at $1100 in my after-tax account. I feel like I can easily make my current net income by selling premium in my after-tax account with puts and BPS. I actually enjoy trading options from time to time even after losing 6 figures the other day when the stock gapped up 20%. I think I should be able to trade options maybe one week or two weeks out of the month to match my current paycheck. What I am finding really hard to do is quitting my job; it is really scary to take the plunge. I actually think it would be better for me to get laid-off because I think I would receive about $150k on a severance package and stock which would be really nice. I think my main worry is that my current job is really high paying for my qualifications, location and is easy and I am afraid I would not be able to find another like it if I ever need to work again. Any thoughts? suggestions?
My old job had that dynamic of being higher paying than anything I'd be able to replace it with in my geography. There's more flexibility now with working from home, but I suspect I still wouldn't have been able to replicate the wages.

Then again, if my salary had been cut in half finding an alternative, I was confident that I COULD find something I'd like at 1/2 or better and if I subtracted out some of the claims on that salary (savings in 401k, company stock, whatever) and some early retirement expenses that don't exist while working (medical is the primary thing that comes to mind), then we could live just fine on a 1/2 salary. So there was a backup plan for retirement, at least in theory. In practice its taken less than 6 months for me to become useless as a full time worker - I'm barely useful doing some 1/2 time volunteer work using my work skills :)

I also went through the thought process that I'd like to be laid off. I finally gave that up - if the severance actually made a difference to a retirement decision then I was probably cutting things too closely on being able to retire. And besides that's an awfully big decision to fork over to somebody else to make for you.


An idea - not advice. If you've done some looking around then you've got an idea of what alternatives you -could- find if you went looking. And I hear that companies are having a hard time finding workers, so maybe getting the new job won't be that hard, even if its half pay compared to what you have now.

Maybe its time to 'buy' yourself a treat and take a 6 month sabbatical. Maybe a personal leave from work for 6-12 months is in order, as a way to take retirement for a test drive.
 
Greetings fellow wage slave! lol
I was in a similar situation earlier this year where the numbers got big enough to give me less of a reason to care about work.
So - the wife retired in October (41 years old) and instead of myself also retiring, I opted to make the time worth more.
This was achieved by thinking through what made me want to work (43 years old) and for me there is a nice sense of purpose and I like my job.
Just because I don't "have" to do it anymore has made it more fulfilling. Not sure why but it helps smooth out any of the good/bad balance of going in everyday.
Also picking up a new Model S Plaid tomorrow since, why not? Giving myself some little treats and saving 100% of my salary is nice and helps me go through the motions of "being retired" but not the stress.
When the wife retired I was a little stressed since it was nice to have her income (nurse practitioner) and insurance but after the first couple of weeks it went away when I saw how happy she was, and that made me happier at work of all things.

Sorry for the long (not @adiggs long.... :p ) rant about my personal choices and situation so not sure if that helps....

What we are really doing at work is selling our time. Time that we can never get back.
If you have more valuable things that could be done with your time, then that would be the way I would look at it. Do those things.

Maybe (since you were just promoted) talk with your company - manager, boss whatever they are called now a days, and let them know your thoughts.
Might be able to trade some salary for extra vacation time and that would be a good balance.

I've been in this position for over 2 years now. Lots of it due to TSLA, but others due to my small business. In fact, I recently cashed out some LEAPS which went ITM to pay for my new home under construction in FL. What keeps me hustling is the pure joy and satisfaction I get from my work. I was going to try to slow down next year and just work 20 hours a week, but honestly, I find it fun and am able to multi-task with other "work" I have to do around the home (grilling, chores, etc.).

I am also in the process of obtaining my instrument rating :). After that is done, along with my move to FL/settling in my new home, I am going to try to "force" myself to go part-time and try to "relax" and enjoy semi-retired life!

Congratulations to everyone on here that is afforded this luxury of life - It's such a blessing!
 
If you are working even after you made it, think of it as working to pay off taxes ;) (tail wags the dog)

I am planning an off year :) and just trade options LOL ;)

+ 6-7 years ago, in my learning journey, I saw a guy who traded made money and travelled the world. If family/children school etc baggage wasn't there I guess this would be a sweet option.
 
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Not advice:
So here's a fun thing for US residents.
If you leave a job at or after age 55, you can access the 401k from that job penality free (versus the normal 59-1/2 age limit).
While employed, you may be able to rollover other 401ks and IRAs (but not Roth) plan permitting.
This means access to your accounts up to 5 years earlier.

So one could get a job with a 401k plan at 54, rollover everything into it, and retire (again?) in the calendar year they turn 55 with full access (minus taxes) to their account.
 
Not advice:
So here's a fun thing for US residents.
If you leave a job at or after age 55, you can access the 401k from that job penality free (versus the normal 59-1/2 age limit).
While employed, you may be able to rollover other 401ks and IRAs (but not Roth) plan permitting.
This means access to your accounts up to 5 years earlier.

So one could get a job with a 401k plan at 54, rollover everything into it, and retire (again?) in the calendar year they turn 55 with full access (minus taxes) to their account.
Sweet...what about just doing a 72-T a lot earlier? Hoping none of the tax laws change around all this...I was going to plan for this as a worst case scenario fall back plan for $!
 
Non advice thoughts:
If your job is more positive than negative, no reason not to stay employed for now. It gives you an income cushion, helps with insurance, and gets you closer to retirement age.
If you are much younger than 60 and have IRA's maybe look into a ladder Roth conversion to allow access to those monies (the roll over amounts) in 5 years. Just opening and contributing to a Roth (if you don't already have one) starts the earnings 5 year clock which matters if you are >55. There is also a rule on 401ks for early penalty free access if you leave/ lose your job and are at least 55.

Also, maybe consider trading the puts more often at further OTM strikes to reduce risk.

Right now is more negative than positive. I am 36 right now so I have a long way to go to.

Greetings fellow wage slave! lol
I was in a similar situation earlier this year where the numbers got big enough to give me less of a reason to care about work.
So - the wife retired in October (41 years old) and instead of myself also retiring, I opted to make the time worth more.
This was achieved by thinking through what made me want to work (43 years old) and for me there is a nice sense of purpose and I like my job.
Just because I don't "have" to do it anymore has made it more fulfilling. Not sure why but it helps smooth out any of the good/bad balance of going in everyday.
Also picking up a new Model S Plaid tomorrow since, why not? Giving myself some little treats and saving 100% of my salary is nice and helps me go through the motions of "being retired" but not the stress.
When the wife retired I was a little stressed since it was nice to have her income (nurse practitioner) and insurance but after the first couple of weeks it went away when I saw how happy she was, and that made me happier at work of all things.

Sorry for the long (not @adiggs long.... :p ) rant about my personal choices and situation so not sure if that helps....

What we are really doing at work is selling our time. Time that we can never get back.
If you have more valuable things that could be done with your time, then that would be the way I would look at it. Do those things.

Maybe (since you were just promoted) talk with your company - manager, boss whatever they are called now a days, and let them know your thoughts.
Might be able to trade some salary for extra vacation time and that would be a good balance.

Great feedback. I am probably going to talk to my boss about giving me a different project to see if I can get some joy back. My job is really easy and I only work 4 days a week and from home. I just can't stand the office politics, the disorganization and ineptitude of my work right now. You are going to love the Plaid.

I'm opting out of stock options. Can't be bothered. But about the other options of life:

I too used a long time to become retired. Perhaps it would calm the butterflies in your belly to remember that you can get another job after ie. a year if you find you miss working too much. Depending on what your job situation is of course.

For me that option is so far forgotten as it can be!

This is true.

A good call on TSLA does not a successful options trader make.

I am taking about selling options and collecting premium. I have been doing this for 1.5 years and so far it has been good.

My old job had that dynamic of being higher paying than anything I'd be able to replace it with in my geography. There's more flexibility now with working from home, but I suspect I still wouldn't have been able to replicate the wages.

Then again, if my salary had been cut in half finding an alternative, I was confident that I COULD find something I'd like at 1/2 or better and if I subtracted out some of the claims on that salary (savings in 401k, company stock, whatever) and some early retirement expenses that don't exist while working (medical is the primary thing that comes to mind), then we could live just fine on a 1/2 salary. So there was a backup plan for retirement, at least in theory. In practice its taken less than 6 months for me to become useless as a full time worker - I'm barely useful doing some 1/2 time volunteer work using my work skills :)

I also went through the thought process that I'd like to be laid off. I finally gave that up - if the severance actually made a difference to a retirement decision then I was probably cutting things too closely on being able to retire. And besides that's an awfully big decision to fork over to somebody else to make for you.


An idea - not advice. If you've done some looking around then you've got an idea of what alternatives you -could- find if you went looking. And I hear that companies are having a hard time finding workers, so maybe getting the new job won't be that hard, even if its half pay compared to what you have now.

Maybe its time to 'buy' yourself a treat and take a 6 month sabbatical. Maybe a personal leave from work for 6-12 months is in order, as a way to take retirement for a test drive.

I really don't think I want to look for another job right now I just need a break and I don't feel like looking at all.

As far the laid-off thing, I am not saying that I will do a bad job to get laid-off but I will ask my boss for a voluntary laid-off if the situation arises; if they need to meet a quota or something. $150-100k extra do not hurt anyone lol. Yes I might also have a discussion with my boss if I can take a sabbatical or something to regroup.

Thanks for the feedback everyone.
 
I love to see this thread at the top, it means we're all doing well.

I'm planning to start taking 72T payments next month after I get some of these CCs exercised against me in my IRA (if I would only stop rolling them). I believe I can replace the majority of my salary with the 72T payments and can sell BPS on top of that. What's holding me back from fully retiring is my age (20+ years from retirement age), high salary, large mortgage, and two young kids.
 
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Sweet...what about just doing a 72-T a lot earlier? Hoping none of the tax laws change around all this...I was going to plan for this as a worst case scenario fall back plan for $!
That is also a valid route. The caveat being, it locks up the IRAs it's based on and any departure from the plan hits all previous withdrawals with the 10% penalty. I think you can create a separate IRA to isolate the impact.
Another issue is 2 out of 3 plan amounts are fixed based on inital balance and the currently really low interest rate. So growing the account does not help until post 59-1/2, unless you start with or switch to the RMD setup (which you can do one time after plan start). RMD gives the least to begin with, but does track account value so you can start with a higher amount then switch to RMD when they hit parity.
 
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That is also a valid route. The caveat being, it locks up the IRAs it's based on and any departure from the plan hits all previous withdrawals with the 10% penalty. I think you can create a separate IRA to isolate the impact.
Another issue is 2 out of 3 plan amounts are fixed based on inital balance and the currently really low interest rate. So growing the account does not help until post 59-1/2, unless you start with or switch to the RMD setup (which you can do one time after plan start). RMD gives the least to begin with, but does track account value so you can start with a higher amount then switch to RMD when they hit parity.
Interesting! I have all types of retirement plans - Roth IRA, Traditional IRA (Rollover), SEPP, 401kh?, Cash Balance, and Profit Sharing.

Are you saying I could isolate the 72T to my SEPP which has about $1M and it doesn't impact the rest? I would follow all the rules and procedures for the 72T up until 55. I'm 37 now, so for 18 years. I.e., $50,000 per year for at least 18 years (when I hit 55) which would be about $900k?
 
Are you saying I could isolate the 72T to my SEPP which has about $1M and it doesn't impact the rest? I would follow all the rules and procedures for the 72T up until 55. I'm 37 now, so for 18 years. I.e., $50,000 per year for at least 18 years (when I hit 55) which would be about $900k?
Correct. The 72T plan applies to a account, or group of accounts, that you specify when you create the plan. For example, you could split a Rollover IRA into two accounts and create a 72T plan against one of them.
 
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Interesting! I have all types of retirement plans - Roth IRA, Traditional IRA (Rollover), SEPP, 401kh?, Cash Balance, and Profit Sharing.

Are you saying I could isolate the 72T to my SEPP which has about $1M and it doesn't impact the rest? I would follow all the rules and procedures for the 72T up until 55. I'm 37 now, so for 18 years. I.e., $50,000 per year for at least 18 years (when I hit 55) which would be about $900k?
The 72(t) aka SEPP stays active and in effect until 5 years after start or 59-1/2 whichever is later. So you would not be able to stop it at 55.
Also, if you use a SEPP on a Roth, the amount pulled out that is earnings is taxed if you are still under 59-1/2 (contributions get pulled out first).
 
The 72(t) aka SEPP stays active and in effect until 5 years after start or 59-1/2 whichever is later. So you would not be able to stop it at 55.
Also, if you use a SEPP on a Roth, the amount pulled out that is earnings is taxed if you are still under 59-1/2 (contributions get pulled out first).

For people with high balances in an IRA and a Roth who want to maximize their 72T distribution: You can include the balance of the Roth along with the balance of the IRA to increase the amount of the 72T distribution, and then choose to only take distributions from the IRA to prevent being double-taxed on the Roth earnings.
 
For people with high balances in an IRA and a Roth who want to maximize their 72T distribution: You can include the balance of the Roth along with the balance of the IRA to increase the amount of the 72T distribution, and then choose to only take distributions from the IRA to prevent being double-taxed on the Roth earnings.
Great advice all around! I didn't know all of these details.

Is there a service or some sort of specialized CPA/Financial whiz type provider that I could consult *IF* I wanted to go about 72-T?
 
Someone posted somewhere on here a couple weeks ago about the Portuguese Golden Visa process. Has anyone here (or someone you know) actually gone through this process? I am seriously considering it and would like to hear about it from someone with firsthand experience. DM me if you prefer.
 
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Someone posted somewhere on here a couple weeks ago about the Portuguese Golden Visa process. Has anyone here (or someone you know) actually gone through this process? I am seriously considering it and would like to hear about it from someone with firsthand experience. DM me if you prefer.

I'd like to hear about it as well. Last I heard they dropped the required investment from 500K Euros to 300K.
 
Great advice all around! I didn't know all of these details.

Is there a service or some sort of specialized CPA/Financial whiz type provider that I could consult *IF* I wanted to go about 72-T?

Most CPAs aren't very familiar with it. This website has been very useful for me: 72tNET – Retire with Confidence. There are knowledgeable people who will answer your questions on that forum. However, a TSLA investor's account size is probably way more than they are used to over there.

It might make sense to have a thread on here just for 72T as there are probably a lot of us who are far from 59.5 and sitting on big retirement accounts that we can't yet access without penalty.
 
Most CPAs aren't very familiar with it. This website has been very useful for me: 72tNET – Retire with Confidence. There are knowledgeable people who will answer your questions on that forum. However, a TSLA investor's account size is probably way more than they are used to over there.

It might make sense to have a thread on here just for 72T as there are probably a lot of us who are far from 59.5 and sitting on big retirement accounts that we can't yet access without penalty.
Done!
US Resident Early Retirement Strategies
This thread also covers it a bit:
When to retire?
 
Still working, but starting to sell a few shares to pay some bills, debt used to buy shares, taxes. Mostly for peace of mind/flexibility.

UK, so we get a Capital Gains Tax allowance of £12,300/$16,544 each every year (£24,600 for a couple)- will be well within that. Only applicable to a few shares I borrowed money to get and are in a taxable account. Rest are in tax-wrappers.

Aim is to maximise tax allowances between (2 people in couple)
  1. Yearly CGT allowance - I want to run these shares down a little in case tax law changes, but they can be untaxed if sell a few each year
  2. (when retired) -
    1. Pension SIPP - 25% untaxed, 75% taxable as income (at 0-55% tax rate - complex)
    2. Other pensions that I couldn't transfer to SIPP - taxable as income (20% most likely, but 0-45% possible)
    3. State pension from 67 or 68 - taxable as income I think
  3. Lastly ISA to fill any gaps (before retirement age of 55-68 especially). This is untaxed (both Capital gains & Dividends for UK, but 15% Dividends USA tax)
So, no taxes in near future, but eventually up to 55% (unlikely) if Tesla goes bonkers & my SIPP goes over a threshold.

Very much dependent on when I (we) retire & how much we take to live on/spend.