The “Two-Way Door” Framework: How to Try On Major Financial Decisions

Jonny Jonson is a financial advisor at Compound who specializes in helping tech professionals and high earners navigate complex financial decisions including career transitions, family planning, and major life changes.

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Career changes, family planning, lifestyle transitions — they all call for some major decision-making, and sometimes a shift in thinking.

The worst thing you can do? Get analysis paralysis. 
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Not every financial choice you make is going to alter your life forever, and letting them weigh on you might mean preventing growth. Calculated risks shouldn’t be scary. And you shouldn’t be scared that a decision is permanent, either. 

So before you get stuck, remember this: Most major life and career moves aren’t final — they’re just “two-way doors.”

I always go back to the framework I learned from Amazon, which tells you to think of your decisions like “one-way doors” or “two-way doors.” Most decisions — even major life changes — are two-way doors: Even if you go out, you can always come back in.

Deciding Whether a Financial Decision is Right For You

Here are the steps to think through when you’re faced with a big financial choice. 

Step 1: Categorize Your Decision Type

Is the decision really irreversible, or does it just feel that way? Usually career and lifestyle decisions are a "two-way door” with a few extra caveats. (You can’t always get back to exactly where you were before you made the change.)

For example: A manager at a Big Tech company was considering leaving her $600,000/year role to move to Costa Rica with her family. It seemed like a massive, irreversible decision, but it was actually a two-way door with some ramifications. She would be able to return to work, but probably wouldn’t return to the same company, or at the same level once she spent time away. Because she was such a diligent saver, she created a sizable financial base that gave her this flexibility without drastically changing her long-term plans.

Putting this step into action:

• List what factors you think make your decision "permanent," and consider whether you’re making assumptions or stating facts
• Look into how other people in your field have gone through similar transitions and what happened when they tried to return to work
• Distinguish between "difficult to reverse" and "impossible to reverse"
• Consider the typical career trajectory for the position you’d seek following your sabbatical or other life transition. What would need to happen after for you to land the role?

Once you’ve decided what type of decision (or “door”) you’re looking at, you can start thinking about your path forward and the level of risk you’re comfortable with.

Step 2: Design Your Own Trial Period

Whether you’re looking at a one-way door or a two-way door, there’s always a way to test the waters before going all in. Try to incorporate a trial period that lets you experience the change without full commitment. This cuts down on the stakes and gives you real-world data for your final decision.

For example: One client wanted to quit their job to be a stay-at-home parent — first, they negotiated for extended parental leave or a sabbatical. That way, they could "try on" the lifestyle and see if it’s what they actually wanted. 

Putting this step into action:

• If you’re considering a career break, negotiate a sabbatical, extended leave, or reduced hours before making permanent changes
• Take on consulting projects in a field you want to move into while keeping your current job
• Move to your target location for a few months before relocating permanently
• Test entrepreneurial ideas as side projects before leaving employment

Once you’ve made a trial strategy, you need to create some financial flexibility so you can experiment while worrying less about your bank account. 

Step 3: Build Financial Cushions for Flexibility

If you set aside some money for the transition period, embracing changes long-term is going to be easier. A good way to prepare is through strategic investments and budgeting, designed to grow your wealth. 

An advisory partner like Compound can give you a holistic view of your financial picture, and how flexible you can afford to be. Before a transition, you need to make sure your finances are in order and that you have the emotional and financial security to dip into your funds in ways that benefit the life you want.

For example: The employee who wanted to take a sabbatical knew that they wouldn’t be able to save for a couple of years. However, she had built up the financial stability to afford the flexibility — and the opportunity to live in another country with her family was priceless. Plus, she and her husband would still be able to meet their retirement goals despite the pause in saving.  

Putting this step into action:

• Build a "flexibility fund" for transition costs
• Avoid making high-risk financial decisions, like holding onto company equity or investing too much of your money during this time
• Keep more cash on hand when you’re trialing so the stakes are lower

With financial flexibility in place, you can think about the emotional and practical information you need to make a decision.

Step 4: Look at Multiple Perspective Points

Don’t just focus on the direct financial costs. Think about the value of your decision in other currencies. The decision you’re making might feel like a risk financially, but what kind of value adds will the change provide you with? More time with your family? Fulfilling a life-long dream? Thinking about your decision through this lens can help you weigh the benefits against the cost.

For example: For the employee taking sabbatical, she knew that it was a once in a lifetime opportunity she’d regret not taking. With a clear view of her financial picture and an understanding of the risks, she knew it was a decision worth trying on.  

Putting this step into action:

• Identify two or three different lenses for viewing your decision (time, money, career growth, family impact)
• Talk to people who have made similar transitions, both successfully and unsuccessfully
• Consider both quantitative impacts (salary, savings rate) and qualitative factors (stress, personal fulfillment, time away from work)
• Set a personal deadline for getting different opinions before making your final decision 

Your biggest asset, at the end of the day, is your time. Typically, it’s better to make one decision with flexibility than to later course-correct a more permanent one. When you try on your decision, you’re taking small steps that save you time and headache later.

Feeling Good About What’s Next

The real power of the two-way door framework: recognizing that you can come back from most decisions and return to the life you had before (or something close). When you properly assess whether you're dealing with a reversible situation, you can make decisions more quickly and with greater confidence. 

That means cutting down on decision-making anxiety. Calculated risks won’t seem so scary, and you can explore new paths without being afraid that you’re making a big mistake. 

Remember: Most financial decisions are actually reversible "two-way doors." Once you internalize this, you'll feel empowered to build the life and career you want, knowing you can always find your way back if things don't work out as planned.