Money Mindset

The Financial Costs (and the Potential Wins) of Starting Over

Money touches most parts of life, which makes starting over feel risky. But fear doesn’t have to decide for you. This piece unpacks the emotional and financial realities of change, and how to rebuild stability, confidence, and freedom on your own terms.

Article

The Financial Costs (and the Potential Wins) of Starting Over

Topic

Money Mindset

Author

Jen Swindler, MFPA, CFP®, CDFA®, AFC®

Money touches most parts of life, which makes starting over feel risky. But fear doesn’t have to decide for you. This piece unpacks the emotional and financial realities of change, and how to rebuild stability, confidence, and freedom on your own terms.

The Financial Costs (and the Potential Wins) of Starting Over

So often, we’re afraid of making life changes for financial reasons, particularly fearing negative financial consequences. 

We’re afraid to move to a new city, to change jobs, to leave a relationship, (for more reasons than strictly financial ones), but money is often one of our primary fears when making life changes. 

There certainly are costs, and the costs are easy to focus on. However, the wins can be exponential and far-reaching, and I don’t think we focus enough on what those wins look like. 

Financial fear is powerful

Money touches so many parts of our lives, and represents much more than numbers. It can be tied to security, identity, and control. Life changes can often threaten this sense of security. 

It brings to mind Maslow’s Hierarchy of Needs; physiological needs are at the base of the pyramid, and the next step up is safety (personal security, employment, resources, health, property). Money is heavily intertwined with both of these foundational layers. 

Maslow's hierarchy of needs

The challenge is that when we’re trying to make a big life change, we’re often reaching for things at the top three portions of the pyramid: love and belonging, esteem, and self-actualization. To reach those higher levels, we have to confront our fears around the lower ones, especially the financial fears that make us feel unsafe. 

Financial fear is so powerful because it’s about much deeper needs that money represents. 

In behavioral finance, extensive research has shown the reality of loss aversion. This means the pain of loss usually outweighs the joy of potential gains. When we’re making a big life decision, the potential loss feels disproportionately worse than the potential gain feels. We tell ourselves that staying in the status quo is safest, even if it slowly costs us something greater: our energy, creativity, peace of mind, or happiness.

Financial fear is not irrational, because stability means survival. But sometimes that instinct can hold us in places we’ve already outgrown.

The Hidden Costs of Playing It Safe

When we think about money and risk, it’s easy to focus primarily on what we might lose. But there is also always a cost to not changing. 

Opportunity cost is the value of what you give up by choosing not to act. For example, staying in a job that feels secure but is burning you out might seem responsible and even necessary, but what about all the parts of your life you’re missing out on because you never have time or energy for them? Over years, that adds up to so many missed opportunities and compounding growth. 

Maybe you’ve stayed in a relationship because managing money in this economy feels overwhelming. Yet every month of emotional exhaustion can result in drained savings through retail therapy or a partner’s spending habits. From personal experience, leaving my marriage at age 24 was terrifying. My partner made the majority of the household income (along with the bad financial decisions). I was terrified I wouldn't be able to make ends meet, but being in control of my finances removed so much financial stress from life. I never knew I would feel better about my situation so quickly after starting over. 

In the work I’ve done with divorcing clients, I’ve seen dozens of situations where people are faced with the exact same situation. It’s usually not very long post-divorce that people see how good the decision was financially (and usually for other reasons, too). 

Playing it safe can feel like protection, but sometimes it’s the more expensive choice long-term.

What the Wins Can Look Like

While the costs of change are usually quite visible and quantifiable, the wins often happen quietly and multiply exponentially over time. 

When someone makes a move that aligns with their values and intuition, their financial confidence usually grows. I’ve seen clients leave high-stress jobs for more balanced lifestyles to find their health improves, creativity returns, and new income opportunities arise. When you’re not constantly in survival mode, you can make clearer, calmer decisions surrounding your finances. 

I was terrified to leave my 7-year-long relationship. We were doing reasonably well financially, but I’d just started my firm about a year prior and some months felt tighter than others. I finally took the leap, knowing it was right for my long-term life, and perhaps it is a coincidence, but the month after I left I exceeded my prior best revenue month by a significant margin. I had so much energy to put into my business. I was happier, and prospective clients could feel that (turns out, people seem to generally prefer a happy financial advisor). I can’t know all the ways that leaving has benefitted (and will continue to benefit me), but I do know that living your best, most joyful, aligned life pays off in countless ways. And I believe that some of those rewards are financial. 

Me with my doggo a few weeks after my breakup. To say I have a new lease on life is an understatement.

Like with investing, these types of financial gains might not be extremely obvious at first, but the compounding is happening and will become increasingly apparent with time. Money can start to feel like a resource that supports your life, not something that dictates it. 

How to Prepare for a Change Without Derailing Financial Stability

Fear thrives without a plan. If you’re considering a big life transition, take time to build a financial foundation that helps you feel secure. 

  1. Assess your financial runway. How many months of expenses could you cover if income is reduced or gone? Know your number. 
  2. Create a transition budget. Estimate the short-term costs of the change. For me in my recent breakup from a long-term relationship, I had to furnish a new place since leaving most of our shared things behind minimized friction. I spent several thousand dollars in the first couple of months, but reminded myself it’s okay to spend my emergency fund in these situations. That’s what it’s for, after all! 
  3. Build flexibility. Can you add side income, reduce financial commitments, or create a backup plan while transitioning? 
  4. Get support. Talk through your plan with a financial planner or a trusted friend. This can help bring perspective and peace of mind. 

Financial planning is partly about making choices that let you live in alignment with your values while still feeling safe. 

Consider journaling about the following prompt: What would I do if money weren’t the biggest fear?

Shifting the Narrative from Fear to Freedom

What if the question was not “can I afford this?” but “what would it take to afford this?” 

Shifts like this can open up creativity and possibility and help us live in a more abundant place energetically. These types of shifts can move you from fear to strategy. Money is not supposed to be a prison – it should support your freedom and the life you wish for. 

Financial freedom is not just about wealth. It is about confidence. I’ve seen so many clients who have all the wealth they need, but they can’t trust in what they’ve built. They don’t have the confidence to walk away. But when we can get to a place where we trust ourselves to navigate anything that happens in life, our money simply becomes a tool to let us live the way we want to. Money can help our lives feel like they truly belong to us. 

Final Thoughts

The financial costs of change can be quite visible and scary. The rewards, including emotional relief, growth, alignment, and fulfillment, are harder to measure but often worth much more. 

So if you’re standing on the edge of a life change and money fear is holding you back, please, please remember: you can plan for uncertainty, you can plan for reduced income or increased expenses, you can prepare for risks, and you can always rebuild! But you can never get back time spent in a life that doesn’t fit right anymore.

Explore More Financial Insights

Featured

General Advice

Money Illustrated Turns 1: My Favorite Lessons from the Past Year

Reflections on my first year of running Money Illustrated—and how the lessons apply to business ownership, personal finance, and life.

Read the article

Featured

Credit Scores, Management, and Protection

16 Billion Reasons to Freeze Your Credit File

In June 2025, Cybernews uncovered the largest password leak in history: over 16 billion compromised credentials. One of the most effective ways to protect yourself is by freezing your credit. Click here to read more.

Read the article

Featured

Budgeting & Cash Flow

How Aligning Your Values with Spending Makes Budgeting Easier

Read the article
No items found.