Practical planning, community, and finding your next chapter, inspired by a conversation with Erika Andresen on Widow Wisdom and Wealth.
I thought we were going to talk about business continuity.
When Erika Andresen joined me on Widow Wisdom and Wealth, I had a list of things I wanted to explore. What happens when a business owner dies? How does a surviving spouse keep the business running? What should families have in place before something unexpected happens?
Those are important questions, especially for widows and widowers who are raising children, managing a career, or suddenly responsible for a business their spouse once ran.
But our conversation opened into something much more personal.
We talked about losing a parent. Starting over after a relationship ends. Changing careers when the familiar path no longer feels right. Accepting help. And learning to recognize progress when life looks very different from the one you expected.
Erika’s work focuses on helping businesses prepare for disruptions. What stayed with me was how much of that thinking applies to the business of living after loss.
When your spouse dies, the responsibilities keep coming. Bills still arrive. Children still need you. There are decisions about work, the house, accounts, and sometimes an entire business. All of that can land at a time when even an ordinary day feels difficult.
Building resilience after losing a spouse can begin with making those responsibilities more manageable, finding people who can support you, and taking one practical step at a time. It can also mean allowing yourself to imagine a future without needing to know exactly what it will look like.
What Does Resilience Look Like After Loss?
During our conversation, Erika described the difference between getting back to where you were and developing the capacity to move forward.
That distinction feels particularly meaningful in widowhood. The life you shared with your spouse cannot simply be restored to its previous version. Your routines, responsibilities, relationships, and sense of yourself may all be changing.
Moving forward can mean learning how to live with that change while continuing to care for yourself and the people you love.
Sometimes it looks like understanding an account your spouse always managed. Sometimes it looks like asking someone to help with school pickup because you have an appointment. Sometimes it is going out to dinner by yourself for the first time.
There may be days when you handle a difficult decision and days when you need someone else to sit beside you while you make a phone call. Both belong in the same life.
One of the things I appreciated about Erika was her willingness to talk about the support she needed along the way. Her background includes corporate law, military service, emergency management, and business continuity. Yet her own transitions still involved uncertainty, grief, and accepting help from others.
Experience can give us tools. We still need somewhere to use them, someone to lean on, and time to find our footing.
Your Next Chapter May Draw on Everything That Came Before
Erika’s career did not follow one straight line.
She began in corporate law, eventually realizing that the work no longer aligned with what she wanted to contribute. Volunteer legal work with veterans helped her see a different direction. She joined the Army, accepting a substantial pay cut because the work felt meaningful to her.
Years later, she decided to leave military service to have more control over her personal life. She submitted her paperwork in January 2020. Then the pandemic changed the employment plans she had made.
She returned to New York and, shortly afterward, her father died. Being there allowed her to spend time with him before his death and help her mother with the estate afterward. She also had time to begin addressing her own mental health needs following military service.
Later, an unexpected relationship breakdown brought another change. A close friend offered her a place to stay in Asheville. While living in her friend’s basement, Erika wrote her first book.
I was struck by how she made use of the experiences she already had. Her legal background, military service, and understanding of emergencies became part of the business she wanted to build: helping other businesses stay in business.
For someone considering a career change after losing a spouse, that is a useful question to sit with: What am I bringing with me?
You may have professional skills, years of managing a household, caregiving experience, community relationships, or an understanding of a problem that other people need help solving. Those experiences deserve consideration as you think about what comes next.
You do not need to have the whole answer today. Sometimes recognizing what you already know is a reasonable place to begin.
Career Changes After Widowhood Have Practical and Personal Sides
For some surviving spouses, returning to familiar work provides structure and connection. For others, the job that once fit their family no longer works with the responsibilities they now carry.
You may need a different schedule because you are the sole parent. You may have inherited a business. You may be considering self-employment, additional education, or a position with less travel.
Erika’s advice was to consider what makes sense to you, rather than relying entirely on what looks sensible to everyone else.
That idea deserves room alongside the practical questions. What would a change mean for your income? Your benefits? Childcare? The amount of savings you would need to use while you transition? How much time and energy can you realistically give it right now?
I shared some of my own experience of starting over at 40 during a different kind of family upheaval. I had children to care for, a mortgage, and a limited amount of time financially to work toward a new direction. Going back to school meant making adjustments to everyday spending.
Those adjustments were part of making the next chapter possible.
Erika also spoke openly about scaling back her spending while building her business. Her experience is her own; a new business has no predictable timetable for becoming profitable. But her story was a reminder that a meaningful change often needs a practical financial structure around it.
For a widow or widower, exploring that structure with a financial professional can help clarify the choices in front of you. You can consider what is workable now, what may need more preparation, and where you have room to move gradually.
What Is the Business of Being Alone?
I sometimes describe part of life after widowhood as the business of being alone.
There is a practical side to it: understanding your finances, knowing where important documents are, and deciding who can help if something happens to you.
There is also a personal side: finding connection, getting support, and making room for a life beyond the responsibilities you are managing.
Erika’s experience helping her mother brought those two sides together. After her father’s death, she helped her mother understand her financial situation and worked through estate matters. But she also noticed that her mother needed reasons to leave the house and spend time around people.
Her parents had been together for 54 years. Her mother was learning how to live without the person who had been beside her since she was young.
Erika encouraged her to go out to dinner regularly. When her mother worried that she no longer knew people at the places she used to visit, Erika pointed out that becoming familiar with a place starts with showing up.
Then she kept checking in about where her mother had gone.
It was such a small, human part of our conversation. And it mattered. Helping someone feel financially supported and helping them reconnect with their community can both contribute to their ability to manage life after loss.
For you, that connection may come through a grief group, a friend, a faith community, a class, or a familiar place where people begin to recognize you. The right pace will be personal.
A Plan Becomes More Useful When Someone Can Follow It
One of Erika’s central points was that having a continuity plan is only part of preparation. The people involved need to understand it and practice how they would use it.
That translates naturally to families.
You may have a folder of important documents. But would the person helping you know where it is? Would they know whom to contact? Would they understand which responsibilities need attention first?
For a sole parent, these questions can feel especially heavy. So much of the family’s daily life may depend on you, from the morning routine to the household income.
Working through one manageable scenario can help you see what is missing. For example, imagine that you are unexpectedly in the hospital for a few days. Who would care for the children? Who knows the school routine? Where are emergency contacts and medication information? Who could help you communicate with your employer or business team?
These are discussion questions to adapt to your own family. The goal is to make the next step clearer for the people who would be helping.
Account access and authority also deserve attention. Knowing a password is different from having permission or legal authority to act. Your attorney, financial professional, and account providers can help you work through what arrangements are appropriate.
When a plan depends on information that only one person knows, that is a useful place to start a conversation.
Business Continuity Matters When a Family Depends on the Business
Some widows and widowers are managing a business they helped build. Others inherit responsibilities they never expected to carry.
There may be employees waiting to be paid, clients expecting work to continue, and family members with different views about what should happen next. The surviving spouse may also be trying to understand who has authority to make decisions.
Erika shared a story about a business owner whose early arrangements had never been revisited. Family members were listed as backups on a business bank account, even though they were not involved in the business. The owner had forgotten putting them there when the company was young.
Reviewing the paperwork brought that old arrangement into view.
It is easy to see how this happens. A business grows. People change roles. Something that made sense years ago stays in place because nobody has had a reason to look at it again.
For a family business, continuity discussions can help uncover those gaps before someone needs to rely on the arrangements. Questions might include who handles payroll, where critical records are kept, which relationships depend on the owner, and who would communicate with staff and clients during an absence.
Succession and ownership decisions bring additional considerations. Those conversations may require coordination among the business’s legal, accounting, financial, and operational resources.
The review itself can be valuable. As Erika explained, participating in the process helps you understand how the business actually works and where it needs support.
Clear Communication Can Help Families Understand Your Wishes
Our conversation also touched on blended families and the emotional side of planning.
A couple may want to care for each other while also honoring commitments to children from earlier relationships. A parent may have a particular wish for an object that carries years of shared memories. People may believe everyone understands what is supposed to happen.
Erika told a story about a friend who had worked on a car with her father and expected to receive it one day. After his death, that expectation did not match the arrangements that were in place.
The car carried meaning beyond its financial value. It represented time together, a shared project, and a promise the daughter believed had been made.
That is why these discussions can be emotional even when the subject appears to be paperwork.
Writing down wishes and reviewing them with the appropriate professionals can help reveal questions that a casual conversation leaves unanswered. For blended families, those questions may involve a home, business interests, beneficiary arrangements, or meaningful personal possessions.
The appropriate documents and arrangements depend on the family and applicable law. What matters at the beginning is giving the conversation enough attention to identify what people intend, what has actually been arranged, and where further guidance is needed.
That clarity can help the people you love understand what you were trying to provide for them.
Small Actions Can Make a Large Responsibility More Manageable
Erika returned several times to the importance of taking action.
Thinking about buying a generator, budgeting for one, and actually having one ready to use are different stages of preparation. The same is true of gathering documents, scheduling a meeting, or talking to the person you hope will help in an emergency.
After losing a spouse, the distance between thinking about something and doing it can feel enormous. Grief, parenting, work, and administrative responsibilities all compete for your attention.
A practical next step might be small: collect the documents for an upcoming appointment, ask an account provider one question, or call the person who has offered to help.
You can also ask someone to share the work. They might take notes during a meeting, organize information with you, or help you make a list of questions. Support can make an unfinished task easier to approach.
And if you prepare for something that never happens, the preparation still has value. Erika spoke about people feeling frustrated when they had prepared for severe weather that turned out to be less disruptive than expected. She saw that as a good outcome: they had developed the capacity to handle a harder situation and did not have to experience it.
For families, the process can also bring useful knowledge into ordinary life. You understand more, the people around you understand more, and a responsibility that once lived entirely in your head becomes something you can share.
Look Back at the Progress You Have Already Made
Near the end of our conversation, Erika shared a practice that had become meaningful to her. Rather than always measuring herself against the distant future she wanted, she began looking at where she was and where she had come from.
She could recognize the home she had made, the work she had done, and the steps she had taken since a devastating change in her personal life.
That stayed with me.
When you are navigating widowhood, there can be so much still to figure out that your progress gets lost behind the unfinished list. You may overlook a decision you have made, a responsibility you now understand, or the moment you finally accepted someone’s offer to help.
Those things count. Their meaning does not disappear when you have a difficult day afterward.
You may still be grieving deeply. You may still be unsure about work, parenting, or the future. Alongside those realities, you can acknowledge something you have learned or managed that once felt beyond your reach.
My conversation with Erika began with business continuity and became a conversation about supporting the life that continues after disruption. Practical preparation, honest conversations, community, and reflection all had a place in it.
If you are navigating life after losing a spouse, perhaps there is one responsibility you would like help understanding, one person you could reach out to, or one step you can recognize yourself for taking.
You can begin there.
Listen to the full conversation with Erika Andresen on Widow Wisdom and Wealth.
Spotify: https://open.spotify.com/episode/1r8uccCYQ2x4qkEkAmykjU?si=e5bddbda1353417d
YouTube: https://youtu.be/-uXeyAbj_vA
Learn more about Erika: https://www.eaasc.com/meet-erika
