Planning for Un-Retirement

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Planning for “Un-Retirement”

HSA Heath Savings Account

Yvonne came to me with one question: “Can I afford to leave this all-consuming stressful job, and instead work at the non-profit I’m passionate about? It won’t pay nearly as much, but I’ll be so much happier!” I’m going to walk you through the process we followed to help her answer that question.

If you’re considering a departure from “corporate,” leaving the comfort of a regular paycheck and benefits, you know it’s a multi-faceted decision. Money is not the only consideration. Nor should it be the most important one!  I encourage all women to think deeply about

  • what brings you joy and gives you energy,
  • how your relationships are affected by your work,
  • your physical and mental health,
  • and how you can move forward feeling engaged and making a difference.

And we must acknowledge the reality of the world we live in. Unless you live off the land, grow your own food, and can fix your own plumbing, you need to think about money!


Here’s my suggested framework to look at your own numbers and decide if you have enough to head out the door.

Step One: What does your current life cost?

There’s no way to get around the need to assess your spending. Lots of women feel really uncomfortable with this part. There’s some unspoken internal (or presumed external) judgment going on – of how many dollars you have and/or where they’re going. Remember – the numbers on the page aren’t judging you! Numbers are just numbers. Whatever shame and guilt you might be feeling is coming 100% from your own head. Please be gentle with yourself! Try to set that judgment aside and instead adopt an approach of scientific curiosity. What can you learn from looking at these interesting numbers?

You need to figure out your Burn Rate. That’s the amount of money you’re spending each month (don’t forget the things that occur less than monthly, like vacations, holidays and gifts, insurance and taxes). Also consider if you’ll need to add in health insurance costs, if that’s something you now get a work but will not in the future!


Step Two: What if you pare it down to the bare minimum?

What’s your “ramen noodle budget?” (BTW I totally stole that term from a client – thanks K.A.!)  This is not about how you want to live, it’s just an exercise to understand if you had to cut down to survival mode, what would that number be? If things go sour, what could you squeak by on?


Step Three: What financial resources do you have?

Add up your assets. This is an important exercise no matter what’s going on in your life! Look at how many dollars you have AND what types of dollars they are. The type of account they’re sitting in affects their liquidity, accessibility, taxation and risk. What are your income sources? Do you have any that would continue if you leave your job? These could be things like rental income, side businesses, annuities – or for the future, pension plans and Social Security.


Step Four: What might your new chapter cost?

Is this change going to require some monetary investment to get started? Training or certification, supplies or equipment, software or subscriptions? Do you need to build a website, rent an office, hire some help? If you’re considering a completely new field and don’t know the answers, find people to ask! Tap your network, and your networks’ network. Remember those Informational Interviews we did back in college days? It’s amazing how many kind-spirited people are willing to help. They can point you toward helpful resources, or suggest mistakes to avoid.

If you will have start-up costs, where is this money going to come from? Do you have savings you can tap? (Ideally not inside your retirement accounts, as they should be earmarked for your living expenses down the road (and remember the 10% penalty that applies to most withdrawals before age 59 1/2). Would you take out a loan? If so, be sure to factor in the loan payments to your future expenses.


Step Five: Calculate your Runway

Math time!  (You can do this – everyone’s phone has a calculator these days. :))

  • Start with how much of your assets you are willing to spend to get going.
  • Subtract any start-up costs (step 4)
  • Divide the result by your monthly Burn Rate (step 1)

The result is the number of months you could float yourself if no revenue comes in from the new initiative.


How does that number feel to you?

If you don’t like the result, are you willing to make some cuts to your ongoing spending? Maybe to move somewhere closer to your ramen noodle budget? How important is this reinvention to you? Are you willing to make some sacrifices? Try to be realistic!

If your answer is zero months, or a very small runway of time, maybe you can set a goal of building up to a comfortable number before you jump. Maybe you start working on the new idea part-time while you’re still earning an income. Or you think about working at Starbucks for the health insurance while you’re ramping up.


Step Six: How much do you think you’ll make?

And how long will it take? Remember it’s always safest to use a conservative number in your projections. We like positive surprises much better than the opposite!

I want to acknowledge that leaving corporate doesn’t always happen on our schedule! Forced reinvention has been a reality, especially for women of a certain age, for a very long time. And COVID has only made it more indisputable. We can’t always lay down these nice, neat plans before we’re off the cliff. So it behooves all of us to have a reinvention plan in our back pockets!

Also consider: What could go wrong?

Some say jumping without a net brings a higher likelihood of success. As a financial planner, I like to err on the other side. Think about the potential pitfalls now, since we humans make better decisions when we’re not in a state of high and stress. What will you do if getting off the ground takes longer than expected; if you reach the end of your runway and income is not covering your living expenses?

  • Would you turn to other ways to bring in some revenue? Think now about what those might be.
  • Would you be willing to sell some of your investments? Decide today in which order and how it would work.
  • Would you ask a friend or family member for a loan? Have some conversations and plant the seed sooner rather than later.
  • Would you tap the equity in your home? Understand the pros and cons of that move and talk to a lender now.

Maybe you have a line you would not cross. You could give yourself a set amount of time, and if it’s not working you move to Plan B. You decide ahead of time on a certain number of dollars of your assets you’ll use, then you’d move to Plan C.


Yvonne’s Happy Ending

Yvonne and I talked through these steps and crunched her numbers. She did quite a bit of self-reflection and talked to trusted people in her life. She decided to save as much as she could for 6 more months, then make the leap. This also gave her time to have an orderly transition in the job she was leaving, to not burn bridges and to keep her network strong. Today she feels lighter and more fulfilled than when we started working together!

Like Yvonne, if you follow this framework, do some math and think through your options ahead, I know you’ll feel more confident moving forward.

Stephanie McCullough

Stephanie McCullough

Founder & Financial Planner

Our focus is working with women 45+ who are facing a financial future on their own and are looking for a true partner in money decision-making. I help professional women reduce financial stress by aligning their money story with their deepest-held values. I am a non-judgmental financial advisor. My team and I work hard to create a safe space to have the intimate conversations necessary. Since money touches all the most important parts of our lives, we have to talk about it all before we can decide what you should do with your dollars.

We will provide you useful and timely information you can use to be #financiallyfearless

Financial steps widow first year

Ask An Expert

Ask an Expert – What financial steps should a widow take in the first year?

Jason Conger Financial Advisor

Answered By

Linda Lingo

Money Coach


What financial steps should a widow take in the first year?


You may be experiencing a range of emotions when your spouse dies. Unfortunately, these feelings don’t go away instantly, and when you start working with your finances, you may feel emotionally overwhelmed. What you are feeling is normal.

However, now is the time you must start pulling the pieces together so you can protect yourself and be your own advocate. It will also be helpful to have a trusted friend or relative help you through this period.

Get a notebook/journal and start writing everything down, because you will not remember having some conversations and certainly not the details. You will feel like you’re operating in a “fog” the first couple of months.


Begin to organize information:

1. Start a filing system for quick and easy retrieval of information.
2. Create a calendar with important due dates.
3. Keep a log in your notebook of actions taken, including the date and contact person.

Contact your professional team: attorney, tax preparer, financial advisor:

1. Gather your estate documents like will, and trust.
2. Talk to your tax preparer about pertinent tax issues for the current year.
3. If you’re the executor of your husband’s will, manage the estate settlement process with the guidance of your advisors.
4. Discuss your finances with your financial advisor.

Review your cash flow for the first year:

1. Prepare a statement listing where money will come from and where it needs to go in the first six months to a year. Include a list of regular bills.
2. Liquidate certain assets that don’t have a penalty such as certificate of deposits or annuities with a death benefit.

Collect benefits:

1. Locate your spouse’s birth certificate, Social Security number, marriage license, military discharge papers, financial account statements and company benefits brochure you may need to collect certain benefits. Keep these papers in your organizational folders.
2. File for Social Security benefits at
3. Contact your life insurance agent to start collecting benefits. Review payout options.
4. Collect veteran’s benefits by contacting the Department of Veterans Affairs if your spouse was in the military.
5. Rollover your spouse’s IRA into your own.
6. Contact the HR Department of your spouse’s employer to collect unpaid salary, vacation pay, sick pay, bonuses, pension benefits, and other benefits due.
7. Take a pension from your husband’s qualified retirement plan or roll it over to your IRA after reviewing the options and your financial circumstances.
8. Contact the financial aid office if you have a child in college. They may be eligible for increased financial aid.

Adjust health and other insurance coverage:

1. Make sure you have your own medical insurance coverage.
2. Notify all insurance agents for auto, homeowners, liability, long-term care, and any other policies.

Review assets and liabilities:

1. Create a financial net worth statement, a list of all you own and what you owe.

Complete the estate settlement:

1. Change the title and beneficiaries on investments, life insurance, vehicles, safe deposit box, retirement accounts. When you’re ready to change the names on your credit card, send it in writing with a copy of the death certificate.
2. Joint checking account should be left open for a year so you can deposit checks payable to your spouse.
3. File an estate tax return if federal or state estate tax is owed. This is due nine months after death.

Take care of yourself:

1. Consider joining a support group for widows or talk with a counselor.
2. Remember self-care including exercise, yoga, meditation, massages, bubble baths, facials, and chocolate!
3. Read a good book about widowhood. There are several good ones, including “For Widows Only!” by Annie Estlund.
4. Keep in touch with your female friends.

Move forward with new goals and your new life:

1. Create an updated financial plan focusing on short-term goals first. Keep it simple and manageable.
2. Update your will and estate plan.
3. Expand your social circles. Meet new people who know you as yourself and not as half a couple.
4. Be careful about entering a new relationship too quickly. Be wary of guys looking for a “purse.” Keep your finances to yourself.
5. It may not seem like it, but there is life after grief.

It’s ok to postpone major decisions during the first year when possible. You don’t need to rush, especially with your big decisions. You will be bombarded by well-meaning friends and family with their suggestions for what “the right decision” is. It can be very helpful to have a trusted friend help you think through some decisions you’ll make. For example, do you pay off your mortgage, or move in with your daughter?

You are at a very vulnerable time following your spouse’s death. Go slowly. Be gentle. Give yourself time to heal.

We will provide you useful and timely information you can use to be #financiallyfearless

Singles taking Ownership of their money

Ask An Expert

Ask an Expert – How can recently single people start to take ownership of their money and money management, especially newly divorced people whose exes controlled the money.

Jason Conger Financial Advisor

Answered By

Maggie Koosa

Financial Planner


How can recently single people start to take ownership of their money and money management, especially newly divorced people whose exes controlled the money.



One who is newly single should take a thorough look of their cashflow, including expenses and income. Living with one income is quite different and affects what excess (not necessary) expenses are tenable.


After working through a divorce, the household assets may be in disarray. One should organize their debts, including mortgage, credit cards, etc and understand due dates and interest rates. They should organize their savings, checking, and investments and understand interest rates, rates of return, allocations, and strategies.


After one has a working understanding of their cashflow, debts, and savings, one can develop a strategic plan to work toward increasing savings (personal and investments), decreasing debts, and working toward their future goals.

* On a side note, newly single people should update their beneficiaries on all of their insurances, financial accounts, estate documents (will, power of attorneys, healthcare proxy, trust), etc to reflect their post-divorce intentions.

We will provide you useful and timely information you can use to be #financiallyfearless

Important ways to Financially Empower your Daughter

Important Ways to Financially Empower Your Daughter


We live in a world where women are 80% more likely to live in poverty after retirement, make only 85% of what their male counterparts earn, and sit in the CEO position of just 7% of Fortune 500 companies. Put simply, it’s a world without equality, and it’s a world in which we should refuse to raise our daughters. It’s true that we are progressively moving in the direction of a better future for our girls, but having these conversations with future women is absolutely crucial to continue our societal growth toward equality. 

In order to have a generation of women who are financially secure, self-reliant, and empower with their money choices, parents today must consciously make decisions that support this. Financial empowerment isn’t something that happens by itself. Instead, we must make the intentional decision to open up and have these conversations, leading by example, and teaching as we go.

Open a Savings Account for Her

Learning to actually save money is probably one of the most challenging lessons for people, so why not introduce the idea from an early age? A savings account is a great way to help make your daughter’s funds feel more “official”, while also relaying the message that you are confident in her ability to understand and manage money. In the beginning, before she has a job or other reliable income, this may just be a place for your daughter to save gifts or allowances she receives over the years. That’s okay! This is an account designed to grow as she does, providing a safe place for her money, allowing her a sense of independence and self-reliance. 

Make sure to bring your daughter to the bank (or allow her to see the screen) when accessing her account, and walk her through some of the words and phrases that may be used in a financial environment. Teach her about interest, and allow her to make some decisions about her own account. It’s not really about the amount of money that’s in the account by the time she’s ready for college (though that might be something she expresses interest in focusing on), but more about getting used to feeling in control and in charge of her own money.

Teach Her to Challenge Gender Stereotypes

While it might seem easy to get caught in the societal trap of perceived gender roles, using phrases like “girl chores” and “boy toys” around your daughters can cause significantly more harm than you might believe. Think about the message you’re sending before you make comments relating to gender, and consider the way it may make your daughter think and feel. 

Instead of simply going with what society has always done, encouraging girls to only nurture baby dolls, dress up in princess dresses, and practice their makeup, make the effort to also surround her with STEM games and financial decisions. Discuss gender roles, and how you see them in the world and on TV. Assure that she is having conversations with male and female role models about money being a shared resource and how everyone can contribute equally. Make sure the conversation always stays open so she knows that she can come to you with any concerns. 

Surround Her with Empowered Women

There are so many women out there who are doing some amazing things for the world. Make it a point to expose your daughter to them. Place lots of focus on reading books with a strong female character and consciously choose movies with an independent girl lead. Show her all the different roles, careers, and titles that can be held by other women. 

By giving your daughter a larger number of women to relate with and look up to, you are only improving her own self-worth and confidence. 


…make the intentional decision to open up and have these conversations, leading by example, and teaching as we go.

Talk With Her about Money

Personal finance can be a touchy and stressful topic for many people to discuss, so it’s no wonder parents naturally feel inclined to shelter their children from the discussion. However, this is probably one of the biggest disservices we can be doing for our daughters, as it is a parent’s job to prepare her to deal with money. 

Of course, there is no reason for your daughter to feel anxiety or any other negative emotion surrounding money, so your discussions should mostly highlight topics like the importance of having an emergency fund, preparing for job loss, and talking about where money actually comes from. Many experts are even beginning to agree that there is no age too early to begin talking with our daughters about money and preparing them to make it.


Final Thoughts

History has taught us that shying away from the tough topics does nothing to solve them, and the same can be said when it comes to the inequality that women face financially. If we want tomorrow’s women to know their self-worth and create their own financial independence, we must not be afraid to have these conversations with even the youngest of them. Don’t ignore the value behind being honest with your daughters about financial successes and insecurities, and always remember that it takes a village of strong, powerful, financially independent women to raise one.  

…there is no age too early to begin talking with our daughters about money and preparing them to make it.

4 Forward-Thinking Reasons to Support Women-Owned Business


4 Forward-Thinking Reasons to Support Women-Owned Business


Believe it or not, women-owned businesses are a vital part of the economy, making up approximately 40% of all privately-held firms, and employing more than 9 million people, according to the National Association of Women Business Owners (NAWBO). Women are the rising entrepreneurial stars of our economy, generating trillions of dollars of revenue per year. Just last year, the US was named the top country for female entrepreneurs by the Mastercard Index of Women Entrepreneurs.

But, there are always two sides to every story, and women entrepreneurs continue to be underrepresented and face obstacles that their male counterparts do not. For example, women are much more likely to face a lending gap, being offered loans that are, on average, 31% smaller than those offered to male-owned businesses. They also experience significant bias when it comes to media reporting, being featured in only 5% of economic news stories, according to The Global Media Monitoring Project

Despite the adversities, women-owned businesses continue to drive substantial economic growth, paving the way for the future female entrepreneurs, and shaking up the traditionally seen male-owned economy. There really are a number of reasons why we should be making conscious decisions to support women-owned companies, but these are our top five. 

1. Women are Better at Building Customer Relationships

In the traditional sense, women are often perceived as the more nurturing and empathetic gender, often being portrayed in roles like nursing and childcare. But the truth of the matter is, empathy is required in all industries, from teaching to construction. In order for any business to do well out there, the owner and employees must be able to connect and communicate with their customers, allowing them to feel valued and appreciated. And research says that women exceed in this arena. Because women tend to be better at multitasking and more empathetic than men, they tend to find common ground with their customers more quickly, looking for solutions to meet the initial problem and help their clients feel whole again. 

Another great reason women are more successful in customer service is that, in a wide range of industries, women are the primary customers. They know what people are looking for and how they want to be treated, giving customers a different experience than what they’re used to having. 

2. Women are Incredibly Innovative

When it comes to penetrating new economic markets, growing a company from the ground-up, and keeping organizations relevant in today’s ever-changing world, innovation is absolutely critical. Today’s entrepreneurs must be adaptable while continuously providing creative solutions for their consumers. From brand-new products and processes to imaginative marketing approaches and business practices, organizations today must constantly be bringing innovation to the market. And, though they may not own quite as much of the market as men, women consistently show that they are just as innovative. 

Research has revealed that, despite the existence of an innovation gap, women entrepreneurs continue to put their innovative ideas into practice just as much as their male peers. There actually are no real gender differences when it comes to implementing creativity into action, with approximately 8 in 10 female entrepreneurs implementing a product or service innovation in their business. 


3. Owned Companies are Under-Funded

While most people are aware of the gender pay gap, more attention should definitely be brought to the fact that businesses owned by women receive significantly less financing than those owned by men. In fact, less than 3% of all venture capital in the U.S. goes to female founders, and they make up only 4% of all commercial loans. The reason for these drastic differences in funding is thought to be due to underwriting bias, different mindsets, and outright sexism. 

 Not only do lenders seem more hesitant to trust women business-owners with larger amounts of money, but they also ask them questions that are more negative than the ones they ask men and are taken much less seriously. Some sources have even discovered that women are only about half as likely to request funding from third-party lenders, and this could be because they are 20% less likely than their male peers, to be approved. 

…women entrepreneurs continue to be underrepresented and face obstacles that their male counterparts do not.

4. Women Entrepreneurs Often Outperform Men

Despite the fact that men seem to own more businesses (more than 75% of businesses are owned by males), and have had the opportunity much longer, than women, female business owners seem to generate more revenue and create more jobs than those owned by their male counterparts. Some data even suggest that women are more effective leaders, with their startups significantly outperforming those owned by males, and many of their companies making the ranks as some of the most valuable organizations in the country. 

Some of the reasons why women seem to outperform men in the leadership sector are due to their higher levels of emotional intelligence and seemingly inborn negotiation skills. Women seem to value relationships more than “winning”, or simply doing business and, in the long run, catering to the human side of business comes out on top.

Final Thoughts

Up until now, women haven’t really been given the opportunity to hold leadership positions or launch their own startups. But, now that they can spread their wings and pour their creativity into these new avenues, consumers are beginning to expect something new. Female entrepreneurs truly bring a new, but very much necessary, level of innovation, creativity, and empathy into the business world, and they are doing exceptionally well. 

Unfortunately, due to years of suppression and blatant sexism, most female business owners must claw and fight for everything they earn. From securing funding, to simply being taken seriously, women are absolutely shaping what it means to be a business owner in all industries. And, because of their dedication to the customer, their continued innovation, and their commitment to hard work, we should all be seeking out new ways to support these female trailblazers. 

There actually are no real gender differences when it comes to implementing creativity into action…