Tyler Olson, EA
@olsonplanner.bsky.social
The physician's financial planner and tax professional.
#MedSky
Planning Services:
www.olsonfp.com
Podcast and Other Resources:
www.physiciancents.com
#MedSky
Planning Services:
www.olsonfp.com
Podcast and Other Resources:
www.physiciancents.com
Pinned
Tyler Olson, EA
@olsonplanner.bsky.social
· Nov 11
This is a safe space for learning about money.
In this new context I thought I should re-introduce myself.
My name is Tyler.
I am a financial planner and tax pro (EA) and I nearly exclusively work with physicians.
Most of my clients are out of training since that is when the very impactful
1/4
In this new context I thought I should re-introduce myself.
My name is Tyler.
I am a financial planner and tax pro (EA) and I nearly exclusively work with physicians.
Most of my clients are out of training since that is when the very impactful
1/4
If you’ve ever wondered whether you’re saving “enough,” this conversation will help you think about the question with more clarity and less pressure
Some households thrive saving 20%
Others do just fine saving less
From today’s new episode:
Some households thrive saving 20%
Others do just fine saving less
From today’s new episode:
December 31, 2025 at 1:55 PM
If you’ve ever wondered whether you’re saving “enough,” this conversation will help you think about the question with more clarity and less pressure
Some households thrive saving 20%
Others do just fine saving less
From today’s new episode:
Some households thrive saving 20%
Others do just fine saving less
From today’s new episode:
You can make a less optimal financial decision and still be making a right one
You just have to understand the tradeoffs
Today's new episode is about two student loan scenarios where the math clearly pointed one way, but the better choice for the family pointed another
Listen on Apple or Spotify
You just have to understand the tradeoffs
Today's new episode is about two student loan scenarios where the math clearly pointed one way, but the better choice for the family pointed another
Listen on Apple or Spotify
December 24, 2025 at 1:55 PM
You can make a less optimal financial decision and still be making a right one
You just have to understand the tradeoffs
Today's new episode is about two student loan scenarios where the math clearly pointed one way, but the better choice for the family pointed another
Listen on Apple or Spotify
You just have to understand the tradeoffs
Today's new episode is about two student loan scenarios where the math clearly pointed one way, but the better choice for the family pointed another
Listen on Apple or Spotify
One bad insurance decision can follow you for decades
In this week’s episode I share some thoughts about:
• Which disability insurance companies I trust
• Why some firms push the wrong products
• The GSI window most residents miss
Listen on Apple or Spotify
In this week’s episode I share some thoughts about:
• Which disability insurance companies I trust
• Why some firms push the wrong products
• The GSI window most residents miss
Listen on Apple or Spotify
December 17, 2025 at 1:55 PM
One bad insurance decision can follow you for decades
In this week’s episode I share some thoughts about:
• Which disability insurance companies I trust
• Why some firms push the wrong products
• The GSI window most residents miss
Listen on Apple or Spotify
In this week’s episode I share some thoughts about:
• Which disability insurance companies I trust
• Why some firms push the wrong products
• The GSI window most residents miss
Listen on Apple or Spotify
If you’re starting fellowship this year, today’s new episode is for you
- Emergency funds
- Disability insurance
- Student loan strategy
- Home buying decisions
You want to create a system so managing your money doesn’t feel overwhelming
Listen on Apple or Spotify
- Emergency funds
- Disability insurance
- Student loan strategy
- Home buying decisions
You want to create a system so managing your money doesn’t feel overwhelming
Listen on Apple or Spotify
December 10, 2025 at 1:55 PM
If you’re starting fellowship this year, today’s new episode is for you
- Emergency funds
- Disability insurance
- Student loan strategy
- Home buying decisions
You want to create a system so managing your money doesn’t feel overwhelming
Listen on Apple or Spotify
- Emergency funds
- Disability insurance
- Student loan strategy
- Home buying decisions
You want to create a system so managing your money doesn’t feel overwhelming
Listen on Apple or Spotify
Had a great conversation with Tyrone Ross about Bitcoin
No unnecessary hype or fear
Just a clear framework for understanding what it is and where it may fit
If you’ve felt curious but overwhelmed, today's new episode is the right place to start:
No unnecessary hype or fear
Just a clear framework for understanding what it is and where it may fit
If you’ve felt curious but overwhelmed, today's new episode is the right place to start:
December 3, 2025 at 1:55 PM
Had a great conversation with Tyrone Ross about Bitcoin
No unnecessary hype or fear
Just a clear framework for understanding what it is and where it may fit
If you’ve felt curious but overwhelmed, today's new episode is the right place to start:
No unnecessary hype or fear
Just a clear framework for understanding what it is and where it may fit
If you’ve felt curious but overwhelmed, today's new episode is the right place to start:
So creepy, docs.
Being chased down by financial advisors?
Shut it down and seek advice from a real financial planner on your specific decisions when you need it.
Don’t let them try to fit their square peg into your round hole.
Being chased down by financial advisors?
Shut it down and seek advice from a real financial planner on your specific decisions when you need it.
Don’t let them try to fit their square peg into your round hole.
December 2, 2025 at 1:25 AM
So creepy, docs.
Being chased down by financial advisors?
Shut it down and seek advice from a real financial planner on your specific decisions when you need it.
Don’t let them try to fit their square peg into your round hole.
Being chased down by financial advisors?
Shut it down and seek advice from a real financial planner on your specific decisions when you need it.
Don’t let them try to fit their square peg into your round hole.
A lot of physicians ask:
“Do I actually need life insurance?”
The real question is:
“Who gets hurt financially if I’m gone?”
In today's new episode, Ronnie and I walk through when you need it, what kind, and how much:
“Do I actually need life insurance?”
The real question is:
“Who gets hurt financially if I’m gone?”
In today's new episode, Ronnie and I walk through when you need it, what kind, and how much:
November 26, 2025 at 1:55 PM
A lot of physicians ask:
“Do I actually need life insurance?”
The real question is:
“Who gets hurt financially if I’m gone?”
In today's new episode, Ronnie and I walk through when you need it, what kind, and how much:
“Do I actually need life insurance?”
The real question is:
“Who gets hurt financially if I’m gone?”
In today's new episode, Ronnie and I walk through when you need it, what kind, and how much:
Time with family
Less stress about taxes
Confidence your assets are protected
Just a few of the real returns on great financial planning
Less stress about taxes
Confidence your assets are protected
Just a few of the real returns on great financial planning
November 21, 2025 at 1:55 PM
Time with family
Less stress about taxes
Confidence your assets are protected
Just a few of the real returns on great financial planning
Less stress about taxes
Confidence your assets are protected
Just a few of the real returns on great financial planning
If you think financial planning is just about investments, you’re missing the big picture
It’s really about:
1) Saving time
2) Reducing taxes
3) Protecting what you’ve built
Today’s new episode breaks down these three pillars of real planning
It’s really about:
1) Saving time
2) Reducing taxes
3) Protecting what you’ve built
Today’s new episode breaks down these three pillars of real planning
November 19, 2025 at 1:55 PM
If you think financial planning is just about investments, you’re missing the big picture
It’s really about:
1) Saving time
2) Reducing taxes
3) Protecting what you’ve built
Today’s new episode breaks down these three pillars of real planning
It’s really about:
1) Saving time
2) Reducing taxes
3) Protecting what you’ve built
Today’s new episode breaks down these three pillars of real planning
If you’re waiting to buy a home until rates drop, you could be waiting awhile
If you’re hoping for lower rates so you can refinance, you could put yourself in a tough spot
A great chat with Matt Graham about mortgages, the Fed, and how to make good decisions no matter the rates:
If you’re hoping for lower rates so you can refinance, you could put yourself in a tough spot
A great chat with Matt Graham about mortgages, the Fed, and how to make good decisions no matter the rates:
November 12, 2025 at 1:55 PM
If you’re waiting to buy a home until rates drop, you could be waiting awhile
If you’re hoping for lower rates so you can refinance, you could put yourself in a tough spot
A great chat with Matt Graham about mortgages, the Fed, and how to make good decisions no matter the rates:
If you’re hoping for lower rates so you can refinance, you could put yourself in a tough spot
A great chat with Matt Graham about mortgages, the Fed, and how to make good decisions no matter the rates:
New episode of A Good Problem to Have is out
This one’s all about cash flow communication
Learning how to manage your spending in a way that keeps you intentional
Whether you're a couple or single, it's important to create the right systems
This one’s all about cash flow communication
Learning how to manage your spending in a way that keeps you intentional
Whether you're a couple or single, it's important to create the right systems
November 5, 2025 at 8:54 PM
New episode of A Good Problem to Have is out
This one’s all about cash flow communication
Learning how to manage your spending in a way that keeps you intentional
Whether you're a couple or single, it's important to create the right systems
This one’s all about cash flow communication
Learning how to manage your spending in a way that keeps you intentional
Whether you're a couple or single, it's important to create the right systems
Reposted by Tyler Olson, EA
A few clients this summer asked the same question:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
October 29, 2025 at 12:55 PM
A few clients this summer asked the same question:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
A few clients this summer asked the same question:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
October 29, 2025 at 12:55 PM
A few clients this summer asked the same question:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
“Can we afford a pool?”
They weren’t short on net worth
They were short on liquidity
And it turned into one of the most interesting planning conversations we’ve had all year
From today's new episode:
The FIRE movement got it wrong for physicians.
You don’t want to quit medicine, you want the freedom to choose it.
That’s Financial Independence, Recreational Employment. 👇
You don’t want to quit medicine, you want the freedom to choose it.
That’s Financial Independence, Recreational Employment. 👇
October 26, 2025 at 12:55 PM
The FIRE movement got it wrong for physicians.
You don’t want to quit medicine, you want the freedom to choose it.
That’s Financial Independence, Recreational Employment. 👇
You don’t want to quit medicine, you want the freedom to choose it.
That’s Financial Independence, Recreational Employment. 👇
If you're offered a guaranteed salary
There are 3 primary things to consider:
1) Time commitments
2) Expectations
3) Tax ramifications
From today's new episode of A Good Problem to Have:
There are 3 primary things to consider:
1) Time commitments
2) Expectations
3) Tax ramifications
From today's new episode of A Good Problem to Have:
October 22, 2025 at 12:55 PM
If you're offered a guaranteed salary
There are 3 primary things to consider:
1) Time commitments
2) Expectations
3) Tax ramifications
From today's new episode of A Good Problem to Have:
There are 3 primary things to consider:
1) Time commitments
2) Expectations
3) Tax ramifications
From today's new episode of A Good Problem to Have:
If you have $150,000 in student loans
There are two main options:
• Going for PSLF
• Paying them off in full
Today’s new episode walks through both of them
Listen on Spotify or Apple
There are two main options:
• Going for PSLF
• Paying them off in full
Today’s new episode walks through both of them
Listen on Spotify or Apple
October 15, 2025 at 12:55 PM
If you have $150,000 in student loans
There are two main options:
• Going for PSLF
• Paying them off in full
Today’s new episode walks through both of them
Listen on Spotify or Apple
There are two main options:
• Going for PSLF
• Paying them off in full
Today’s new episode walks through both of them
Listen on Spotify or Apple
Every year, I see doctors sign 6-figure mistakes b/c they rush through the fine print.
Here’s what to watch for (and what to do instead): 🧵
Start with the big 3:
✅ Comp structure
✅ Termination clause
✅ Restrictive covenants
If you don’t understand these cold, you don’t understand your contract.
Here’s what to watch for (and what to do instead): 🧵
Start with the big 3:
✅ Comp structure
✅ Termination clause
✅ Restrictive covenants
If you don’t understand these cold, you don’t understand your contract.
October 8, 2025 at 7:54 PM
Every year, I see doctors sign 6-figure mistakes b/c they rush through the fine print.
Here’s what to watch for (and what to do instead): 🧵
Start with the big 3:
✅ Comp structure
✅ Termination clause
✅ Restrictive covenants
If you don’t understand these cold, you don’t understand your contract.
Here’s what to watch for (and what to do instead): 🧵
Start with the big 3:
✅ Comp structure
✅ Termination clause
✅ Restrictive covenants
If you don’t understand these cold, you don’t understand your contract.
3 things you can do with your first attending paychecks
1) Pay off high-interest credit card debt
2) Build an emergency fund
3) Max out 401(k) or 403(b)
From today’s new episode of the podcast
Listen on Spotify or Apple
1) Pay off high-interest credit card debt
2) Build an emergency fund
3) Max out 401(k) or 403(b)
From today’s new episode of the podcast
Listen on Spotify or Apple
October 8, 2025 at 12:55 PM
3 things you can do with your first attending paychecks
1) Pay off high-interest credit card debt
2) Build an emergency fund
3) Max out 401(k) or 403(b)
From today’s new episode of the podcast
Listen on Spotify or Apple
1) Pay off high-interest credit card debt
2) Build an emergency fund
3) Max out 401(k) or 403(b)
From today’s new episode of the podcast
Listen on Spotify or Apple
Imagine wanting to go on vacation, checking your Ally vacation savings bucket, and seeing $12,000 in there begging to be spent on a vacation.
October 2, 2025 at 12:55 PM
Imagine wanting to go on vacation, checking your Ally vacation savings bucket, and seeing $12,000 in there begging to be spent on a vacation.
I see a lot of docs get life insurance before they get disability insurance.
You gotta realize something.
You being gone and unable to provide materially for your family is one thing.
You being living through your working years but still unable to provide is
1) more likely and...
You gotta realize something.
You being gone and unable to provide materially for your family is one thing.
You being living through your working years but still unable to provide is
1) more likely and...
October 2, 2025 at 11:33 AM
I see a lot of docs get life insurance before they get disability insurance.
You gotta realize something.
You being gone and unable to provide materially for your family is one thing.
You being living through your working years but still unable to provide is
1) more likely and...
You gotta realize something.
You being gone and unable to provide materially for your family is one thing.
You being living through your working years but still unable to provide is
1) more likely and...
The first episode of my new podcast is officially live
"A Good Problem to Have"
I'll be talking about problems that are unique to physicians and will address a new topic each week
I hope it's a helpful resource for you
This first episode is an intro to me and my background in the space:
"A Good Problem to Have"
I'll be talking about problems that are unique to physicians and will address a new topic each week
I hope it's a helpful resource for you
This first episode is an intro to me and my background in the space:
October 1, 2025 at 12:55 PM
The first episode of my new podcast is officially live
"A Good Problem to Have"
I'll be talking about problems that are unique to physicians and will address a new topic each week
I hope it's a helpful resource for you
This first episode is an intro to me and my background in the space:
"A Good Problem to Have"
I'll be talking about problems that are unique to physicians and will address a new topic each week
I hope it's a helpful resource for you
This first episode is an intro to me and my background in the space:
Buying a home?
The mortgage isn’t the whole story.
Don’t forget the 5 other cash outflows:
✅ Closing costs
✅ Insurance
✅ Property taxes
✅ HOA fees
✅ Maintenance
Plan for these now, or they’ll plan your future for you.
The mortgage isn’t the whole story.
Don’t forget the 5 other cash outflows:
✅ Closing costs
✅ Insurance
✅ Property taxes
✅ HOA fees
✅ Maintenance
Plan for these now, or they’ll plan your future for you.
September 25, 2025 at 12:55 PM
Buying a home?
The mortgage isn’t the whole story.
Don’t forget the 5 other cash outflows:
✅ Closing costs
✅ Insurance
✅ Property taxes
✅ HOA fees
✅ Maintenance
Plan for these now, or they’ll plan your future for you.
The mortgage isn’t the whole story.
Don’t forget the 5 other cash outflows:
✅ Closing costs
✅ Insurance
✅ Property taxes
✅ HOA fees
✅ Maintenance
Plan for these now, or they’ll plan your future for you.
Emergency Fund Goals for Trainees:
1) Save $1,000
2) Then aim for 1 month of expenses
3) If you're able to save 3 months of expenses, that's awesome. But you can begin justifying contributing to your program's 403(b) (especially if there's a match) after you've got 1 month of expenses saved.
1) Save $1,000
2) Then aim for 1 month of expenses
3) If you're able to save 3 months of expenses, that's awesome. But you can begin justifying contributing to your program's 403(b) (especially if there's a match) after you've got 1 month of expenses saved.
September 23, 2025 at 7:54 PM
Emergency Fund Goals for Trainees:
1) Save $1,000
2) Then aim for 1 month of expenses
3) If you're able to save 3 months of expenses, that's awesome. But you can begin justifying contributing to your program's 403(b) (especially if there's a match) after you've got 1 month of expenses saved.
1) Save $1,000
2) Then aim for 1 month of expenses
3) If you're able to save 3 months of expenses, that's awesome. But you can begin justifying contributing to your program's 403(b) (especially if there's a match) after you've got 1 month of expenses saved.
Med students -
If you're not in 4th year yet, you will be soon. And that means extra costs:
- ERAS (or other match-related system) fees
- interview costs
- moving (potentially across the country) costs
- apartment deposit for the new place (or closing costs if you're buying)
It's a lot!
If you're not in 4th year yet, you will be soon. And that means extra costs:
- ERAS (or other match-related system) fees
- interview costs
- moving (potentially across the country) costs
- apartment deposit for the new place (or closing costs if you're buying)
It's a lot!
September 23, 2025 at 7:29 PM
Med students -
If you're not in 4th year yet, you will be soon. And that means extra costs:
- ERAS (or other match-related system) fees
- interview costs
- moving (potentially across the country) costs
- apartment deposit for the new place (or closing costs if you're buying)
It's a lot!
If you're not in 4th year yet, you will be soon. And that means extra costs:
- ERAS (or other match-related system) fees
- interview costs
- moving (potentially across the country) costs
- apartment deposit for the new place (or closing costs if you're buying)
It's a lot!
New attendings -
Here's how I'd direct your paycheck destinations in order of priority:
1) pay off credit card and other high (10%+) interest debt
2) fill up emergency fund (3 months) in a HYSA (or money market)
3) max out HSA (if applicable)
1 of 4
Here's how I'd direct your paycheck destinations in order of priority:
1) pay off credit card and other high (10%+) interest debt
2) fill up emergency fund (3 months) in a HYSA (or money market)
3) max out HSA (if applicable)
1 of 4
September 23, 2025 at 11:18 AM
New attendings -
Here's how I'd direct your paycheck destinations in order of priority:
1) pay off credit card and other high (10%+) interest debt
2) fill up emergency fund (3 months) in a HYSA (or money market)
3) max out HSA (if applicable)
1 of 4
Here's how I'd direct your paycheck destinations in order of priority:
1) pay off credit card and other high (10%+) interest debt
2) fill up emergency fund (3 months) in a HYSA (or money market)
3) max out HSA (if applicable)
1 of 4