iiinova — where your digital self keeps evolving

Tyler Olson, EA @olsonplanner.bsky.social · 2h

You can build all the optionality in the world Yet still not know what to do with it We talk about why so many high earners (doctors included) freeze up when they finally have the freedom to do anything The fix starts long before you retire Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 30/09/2026

You have more room to negotiate than HR lets on - Signing bonus - Schedule and call - Work location - Side gig language - Non-compete terms Know your priorities, then ask Today's new episode all about contracts & negotiation out now Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 23/09/2026

You can't see your own blind spots No matter how smart you are, or how good you are at your job In this week's conversation, we talk about knowing when to bring in outside perspective, whether that's on your money, your contract, or your practice Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 16/09/2026

Own-occupation disability insurance is expensive It's one reason why so many new attendings skip it But think about what it protects • Years of school • Years of training • The income you worked for Today's new episode out now Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 15/09/2026

You went from $70,000 in training to $500,000 as an attending It feels like you can do anything now You can't That income disappears fast if you let your appetite grow with it New episode out now Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 14/09/2026

You can make $500,000 a year and still feel like money's tight And that's not necessarily a bad thing It could mean you're saving 20% for retirement, funding vacations, building savings And there's nothing left to spend on lifestyle creep

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Tyler Olson, EA @olsonplanner.bsky.social · 13/09/2026

A good financial plan isn't about aspirations It's about systems Like retirement contributions that happen automatically That's how a well-constructed plan actually functions

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Tyler Olson, EA @olsonplanner.bsky.social · 09/09/2026

Rushing to pay off student loans can feel productive But it's not always the right move You need to consider: • Your career path • Your taxes • Your mindset • Your cash flow Today's new episode out now Part 3 of the new attending money series Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 02/09/2026

A financial plan doesn't have to be complicated It's four primary pillars: income, expenses, savings, debt Write them down No written plan means no real direction Today's new episode fixes that Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 01/09/2026

Irregular expenses are more regular than you think If you're only tracking the big picture numbers, you're missing the real cost of living, and the real cost of buying a home There's more than the monthly payments From today's new episode of Physician Cents

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Tyler Olson, EA @olsonplanner.bsky.social · 31/08/2026

When buying a home, the sticker price is not the full cost Watch for: - Utility deposits - HOA fees, some run $1,000+ per month - Selling costs if you move again in a few years - Buying costs on the next place This is one of the largest purchases you'll make Know the full picture first

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Tyler Olson, EA @olsonplanner.bsky.social · 30/08/2026

A mortgage payment is not your whole housing budget Repairs and upgrades need their own bucket of money, separate from principal and interest If there's enough in the bucket, you move forward If there's not enough, you wait Build a plan and prepare for the costs

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Tyler Olson, EA @olsonplanner.bsky.social · 26/08/2026

The real problem isn't overspending or underspending It's not knowing your numbers Fix that first Build a cash flow plan, then spending, saving, and paying down debt all get simpler Today's new episode out now Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 19/08/2026

A physician mortgage can be a great tool But just because you're a doctor doesn't mean you automatically need one There are important things to consider before you start shopping for a lender or get caught up in the lowest rate Today’s new episode out now Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 15/08/2026

Buying and selling a home in a short period of time can wipe out a shocking amount of progress Closing costs, moving costs, commissions, and everything else add up fast Unfortunately in today's world, it’s not hard to burn through $100k before you even realize what happened New episode out today

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Tyler Olson, EA @olsonplanner.bsky.social · 14/08/2026

Your contract might look amazing on paper Big base salary, production bonus, quality bonus But what matters is what actually hits your bank account Understand your real income and then choose a home that fits your actual financial life

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Tyler Olson, EA @olsonplanner.bsky.social · 13/08/2026

Around half of doctors leave their first attending position If you buy before you know the job is right, that mortgage can make it a lot harder to walk away from a bad situation Your career and your health are worth protecting

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Tyler Olson, EA @olsonplanner.bsky.social · 12/08/2026

One of the frustrating things about paying off credit card debt is that the balance isn’t static You're paying it down, but you're also continuing to put expenses on the card Today's new episode is all about how to create a payoff plan that actually works Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 05/08/2026

Paying off debt doesn't feel like progress the same way investing does But knocking out 10%+ interest debt is a guaranteed win And once that weight is gone, your income can do what it was meant to do From today's new episode of A Good Problem to Have

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Tyler Olson, EA @olsonplanner.bsky.social · 29/07/2026

Retirement accounts are important But the account that gives you the most flexibility is your taxable brokerage account - No age restrictions - No contribution limits or RMDs - No waiting until retirement to use your money Today's new episode of A Good Problem to Have Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 22/07/2026

A guaranteed salary is a great benefit But treating it like a permanent paycheck can be a costly mistake Before you buy the house or upgrade your lifestyle, make sure you understand what your compensation looks like after the guarantee expires From today’s new episode of A Good Problem to Have

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Tyler Olson, EA @olsonplanner.bsky.social · 16/07/2026

You can try to build the perfect financial plan But six months later, life makes it completely outdated That's not a failure It's the whole point of planning Newest episode of A Good Problem to Have out now

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Tyler Olson, EA @olsonplanner.bsky.social · 08/07/2026

Planning to buy a new construction? Before you take the builder's financing offer, slow down A lower rate, credits, or free upgrades can be a great deal But only if the numbers actually work in your favor From today’s new episode Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 01/07/2026

Today's new episode is all about compensation • RVUs • Contracts • Negotiation Understanding how you're paid isn't just about making more, it's about making informed career decisions Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 30/06/2026

Setting up an S-Corp isn't just about saving on taxes It comes with real responsibilities • A reasonable salary • Bookkeeping • Payroll • Ongoing compliance Don't focus only on the upside Focus on doing it correctly and making the right choice for yourself

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Tyler Olson, EA @olsonplanner.bsky.social · 29/06/2026

1099 income can be an incredible opportunity - Potentially higher pay - More flexibility - Better tax planning But there's also more responsibility and risk involved Understand the tradeoffs before making the leap

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Tyler Olson, EA @olsonplanner.bsky.social · 24/06/2026

Most doctors focus on medicine first, as they should But eventually, many start asking questions about taxes, investing, and financial freedom It’s important to set aside some time to consider & plan for different areas of life Listen to today’s conversation on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 17/06/2026

Starting a business is hard Starting a healthcare business may be even harder This week I'm joined by Dr. Noah Kaufman to talk about the behind-the-scenes realities of launching KaufCare, a direct acute care practice A thoughtful conversation for anyone interested in ownership and independence

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Tyler Olson, EA @olsonplanner.bsky.social · 15/06/2026

You can gradually introduce money conversations You can control how and when information is shared You can't control what happens when assets legally belong to someone else If we're not careful, we can unintentionally create expectations that don't match reality and damage trust along the way

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Tyler Olson, EA @olsonplanner.bsky.social · 14/06/2026

You don't need a perfect college savings plan You need a goal Without a target it's hard to know if you're on track For some families, that means saving whatever fits the budget today For others, it's calculating exactly what it will take to fund a specific school

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Tyler Olson, EA @olsonplanner.bsky.social · 13/06/2026

One of the biggest college planning mistakes? Assuming there's one "right" answer Some families want to cover everything Others want to pay for undergrad and let their kids take it from there The key is deciding what matters most before you start saving and investing

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Tyler Olson, EA @olsonplanner.bsky.social · 10/06/2026

If you're counting on PSLF buyback, this episode is for you Should you keep making payments & hedge against uncertainty? Or stop paying & rely on the buyback process? Neither option is perfect, but understanding the tradeoffs can help you move forward with confidence Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 03/06/2026

An S-Corp can help you save money on taxes But what often gets missed are the expenses, retirement contributions, and administrative costs that reduce the potential benefit Before you jump in, make sure you understand the full picture New episode out today (Listen on Apple or Spotify)

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Tyler Olson, EA @olsonplanner.bsky.social · 01/06/2026

The more I invest, the more I realize simplicity usually wins Early in my career I went down every rabbit hole possible And honestly? Most of it just added stress, complexity, and more things to babysit A good financial plan shouldn’t feel exhausting to manage From today's new episode:

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Tyler Olson, EA @olsonplanner.bsky.social · 31/05/2026

The biggest value add for most physicians is tax planning, cash flow strategy, and building a plan that actually works together Then as wealth grows, the focus can shift toward diversification beyond just public markets The goal isn’t always "beating the market" From tomorrow's new episode:

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Tyler Olson, EA @olsonplanner.bsky.social · 30/05/2026

A lot of physicians are accidentally building scattered portfolios - 403(b) - HSA - Roth accounts - Taxable accounts If you’re making investment decisions account by account, you’re probably missing the bigger picture Your portfolio should work together as ONE strategy, not several separate ones

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Tyler Olson, EA @olsonplanner.bsky.social · 27/05/2026

A good advisor should be able to explain: • How they get paid • Why they’re recommending something • What value you’re receiving If they can’t do that clearly, you should probably keep looking Today’s new episode is all about fees & incentives in the financial industry Listen on Apple or Spotify

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Tyler Olson, EA @olsonplanner.bsky.social · 20/05/2026

A lot of physicians assume they can always “just pick up more shifts” Maybe you can right now But what are today’s financial decisions committing you to 10, 20, or 30 years from now? New episode out now - listen on Apple or Spotify:

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Tyler Olson, EA @olsonplanner.bsky.social · 15/05/2026

Most trainees think they’re “behind” because they haven’t started investing yet But when your future paycheck is $20k+ per month, your biggest asset right now isn’t your Roth IRA It’s your future income Learn the basics, avoid bad debt, and build good habits From today's new episode:

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Tyler Olson, EA @olsonplanner.bsky.social · 14/05/2026

Time is on your side as a physician You don’t need to stress about having everything perfect the second you finish training - Build some cash reserves - Get breathing room - Then crank up retirement savings From tomorrow's new episode of Physician Cents

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Tyler Olson, EA @olsonplanner.bsky.social · 13/05/2026

One of the most underrated financial goals during training: Protecting your mental health Not every dollar has to go toward investing Sometimes the best financial move is creating breathing room, reducing stress, and giving yourself confidence

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Tyler Olson, EA @olsonplanner.bsky.social · 13/05/2026

A lot of physicians assume 1099 income is automatically better But it’s not that simple Yes, there can be major tax and retirement planning opportunities But fewer people talk about: - Higher payroll taxes - Paying for your own benefits - Malpractice coverage From today’s new episode:

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Tyler Olson, EA @olsonplanner.bsky.social · 06/05/2026

You don’t need to wait until you’re making attending money to start building a life you enjoy Yes, your income is lower Yes, you need to be intentional But that doesn’t mean everything has to be put on hold for years From today’s new episode:

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Tyler Olson, EA @olsonplanner.bsky.social · 01/05/2026

Most doctors don’t know what they spend each month Not because they can’t figure it out, but because they don’t want to There’s a little anxiety in looking too closely But if you’re trying decide if you can afford a new mortgage… you need real numbers, not guesses From today’s new episode

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Tyler Olson, EA @olsonplanner.bsky.social · 30/04/2026

You become an attending… and everything starts happening fast Bigger house, nicer cars Then kids, private school, family trips Most people don’t feel the pressure until it’s already there We break it down on tomorrow's new episode

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Tyler Olson, EA @olsonplanner.bsky.social · 29/04/2026

You just finished training and finally have a real paycheck… That doesn’t mean it’s time to buy your “forever home” You’re experiencing a new city, new job, new costs Give yourself time to make sure it actually fits in your life

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Tyler Olson, EA @olsonplanner.bsky.social · 29/04/2026

A will isn’t just about who gets your money It’s about clarity Making hard situations a little bit easier for the people you love Most people avoid this conversation, but you shouldn’t Today’s new episode is all about estate planning:

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Tyler Olson, EA @olsonplanner.bsky.social · 22/04/2026

If investing feels overwhelming right now, that’s normal But you don’t need complexity You need a simple system:   → Automate contributions → Pick a solid fund → Stay consistent From today's new episode (part 7 of the new intern money series):

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Tyler Olson, EA @olsonplanner.bsky.social · 15/04/2026

AI can be helpful, but it can also be wrong We’ve already seen it send back incorrect info to clients If you don’t know how to verify it, that’s a problem That’s why having a human in the loop matters Covered in today’s new episode:

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Tyler Olson, EA @olsonplanner.bsky.social · 15/04/2026

You don’t need 3-6 months saved right now Start with $1,000 Then build toward one month of expenses That’s how you create stability during intern year From today’s new episode (Part 6 of the new intern money series):

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