Widows Returning to Work: Exploring the Challenges and Benefits

The choice of widows returning to work or not after the loss of a spouse or life partner is a difficult one. From the emotional struggles to the practical considerations, this podcast episode sheds light on the complexities of this decision and the variety of ways widows can find flexibility, support, and empowerment navigating the professional world while grieving. 

Melissa shares her journey of remote work, highlighting the delicate balance between managing professional responsibilities and the demands of single parenting. Jen’s narrative underscores the significance of work as a support network, recounting how her colleagues transformed into a second family during her moments of vulnerability. And I share how I took over running my late husband’s business while ensuring flexibility for my family’s needs.

Key topics in this episode:

• the realities and possibilities of reentering the workforce as a widow
• the emotional journey of balancing work, parenting, and personal healing
• insights into alternative job options and healthcare coverage

Each tale resonates with the central theme of adaptation, showcasing the different ways widows can redefine their work-life dynamics in the wake of loss.

Listen to the Full Episode

Links + Resources From This Episode

This post contains affiliate links. Please read our affiliate policy for more information

• Join our Widow Squad private Facebook group here
• FlexJobs – use promo code FLEXLIFE for 30% off an annual subscription
• Fiverr – connects people with freelancers offering digital services in 500+ categories
• VIP Kid – ESL tutoring company
• Etsy – global marketplace for handmade or vintage items

Episode Transcript

Melissa: Hello, Widow Squad Podcast listeners. It’s Melissa Pierce, and I’m here with my co-hosts Jen Zwinck and Kim Murray.

In today’s episode, we’re discussing a decision that many widows contemplate and that is  returning to work after the passing of their life partner. Whether it’s for emotional, financial, or personal growth reasons, it’s a journey filled with mixed emotions. So let’s explore it together.

Jen, can you tell us little bit about your work situation after Brent died?

The Role of Coworkers as a Widow’s Second Family

Jen: Well, I want to start this off by just saying that this topic comes up a lot in our Widow Squad discussions. And we were actually talking about this in our Widow Squad private Facebook group, which, if you’re not a part of that, please sign up because we have some awesome discussions happening in there.

I think we did a poll where we were talking about going back to work and how many people had to go back right away. And a lot of the responses to that poll said that people really wanted to go back to work for a lot of different reasons. They felt it was a way to just maintain some stability, some normalcy. Going back to work is not always a bad thing. And I kind of felt that a little with me. I had some flexibility in going back to work. I didn’t have to go back right away. I didn’t have a set number of bereavement days like many people do. They were very flexible with me, and I’m blessed because of that. I think I took probably three weeks off and then I ended up going back just part time. They were fine with that, so that was a blessing.

My people at work are like a second family, and I know many people experience this. You’re with these people every day, right? Sometimes for years. One of my really close coworkers, Mel, and I had worked together for like eight years. She was one of my best friends and she lived ten minutes away from me, whereas a lot of my family and my close friends didn’t live that close. In those first couple of weeks when I was full of anxiety after Brent was killed so suddenly and unexpectedly, I was in my house by myself with Claire, not feeling safe. I wasn’t feeling secure, and I was staying up all night because I was so anxious and scared and paranoid and all of those terrifying feelings that were flooded with just being in my house.

I can remember two or three nights in those first couple of weeks where I called Mel at like, 9:00 at night and I said, “hey, I am freaking out over here. Can you come over? Can you just come over and spend the night?” And man, she would pack her little bag and she would come over to my house and sleep in the guest bedroom or wherever. She was like, “Sure, I’m on my way. I’m coming.” She would come over. It didn’t matter when. We would stay up and talk a little. She was just there for me, just being there for me as a good friend. And that’s what our coworkers, a lot of times, turn into. They transition into this second family. It was a second family for me. It was so amazing having her there and knowing that when I go back to work, I have this person, this is my support network, this is what I need right now. These people love you. They’re your friends. They want the best for you. They know what your work life is like. When you go to work, what do you do every day? You’re sitting at a desk or you’re answering calls or you’re dealing with the public, you’re in retail or whatever your job is. These people know what you have to deal with every day and your mental capacity for doing the things that you need to do so they can step in if needed and kind of help you get through your day.

I just found that part of being at work very comforting. I knew that these people had my back. They’re going to step in if I have to step out and start crying at work, which, Lord help me, I can’t even tell you how many times that happened where I had to step out. I couldn’t handle the workload and I couldn’t handle my day. These coworkers, they would come in and take over and help me get through my little mini breakdown in the middle of the day.

So anyway, it’s a helpful support network. It can be exactly what you need. If you’re trying to get back to work and have some sense of normalcy, that’s your second family that you can turn to. That’s what it was like for me, and not everybody can do that. It depends on what your particular line of work is. It depends on how many bereavement days you can take. There are a lot of different factors in that. If anybody listening to this is considering going back to work, a good reason to go back is because you have that second family there. That’s what worked for me.

So, Melissa, what about you?

Finding Support in the Workplace

Melissa: Returning to work was interesting for me. I worked remotely, so I worked out of the home, which was great in some ways and not so great in others. I lacked that, being around people. But I had already worked at this company for twelve years in an office situation. I knew everybody. But I think the bereavement policy at the company I worked for was three days. Three days off is not enough time at all. So, I dipped into my vacation. And I had some really good friends in HR. There was no way I would return to work in three days or even a week. They suggested I take a short-term disability, like a stress leave. So, I had to go to my doctor and she’s like, “I’ll sign whatever you need me to sign for however long you need me to do it.” I had to file all kinds of paperwork to get onto short-term disability as a stress leave. And I took five weeks. I could have taken more, but after five weeks, I felt like I was kind of settled. We were into a routine.

I went back to work after five weeks. Honestly, I don’t know if I was super effective at my job at that time. The “widow fog” is real. A lot of my job is to review legal documents and interpret and negotiate with clients. I didn’t ever get any feedback that I had ever messed anything up but I’m sure I wasn’t at my best. I was not at my 100% best.

It was an amazing company, and the people that I worked with were amazing, and they were like family. And most of the dear, dear friends I have to this day are from that work situation. I worked as a part of a really great team. I supported a sales team, and they were fantastic to work with. They lived all over the United States, and I would see them once or twice a year. We just developed a really deep bond, and they took care of me. I can’t even say enough about this team. They were amazing to me, and most of them were dudes. And they were willing to really talk to me about anything. They were really interested in how I was doing. It was like, “how are you doing? We want to know. Are you doing okay? What can I do for you?” I just had this really great relationship with this team and this company. They treated me very well.

I needed some normalcy. My kids needed some normalcy. It was normal for me to work from eight to five. I needed to do that. Whether I did it effectively or not was another question. But it was comforting to just know that I had a little bit of a routine, and so I liked that. After that five-week short-term disability, I ended up continuing to work there for another year and a half or so.

It eventually became too much for me to handle, in addition to taking on the solo parenting and processing my grief. I was kind of putting the grief off and then it decided to catch up with me. Trying to process my grief, support my kids and their grieving, and work full-time was way too much. All the plates were spinning and some of them were starting to crash. I kind of had a little mini nervous breakdown at work. I call it a mini nervous breakdown. Nobody around me knew because I like to present, like, I’ve got it together. But I just started crying in my cubicle. I had moved back to Portland, so I was in the office at this time, and I was just like, I cannot do this anymore. I cannot do this. And so, I’m just like crying in my cubicle. And my friend in HR pulls me in to her office and she’s like, “what’s happening? What just happened?” And I said, “I can’t do this.” This was on a Friday and she’s like, “just go home. Let’s talk about it on Monday.” By Monday I was like, I’m out of here. I gave them like four- or five-months’ notice. I just decided I need to be a full-time parent.

I didn’t know how I was going to do it, but I need to be a full-time parent and I really need to do the work. My kids and I did the work of grieving and processing the trauma and what had happened to us. Once I gave that notice, it was like, oh, it was the best four months of my life. It was like, whew. No pressure. Because I knew I wasn’t going to be working and I was really going to be focusing on me and my kids. And they were fantastic. They totally understood.

I stopped working for them for about two and a half years. And then I went back, and I worked for them again for another two and a half years. The minute they knew I was kind of dipping my toe into the employment space, they heard about it and they’re like, yes, we want you back. They didn’t know in what capacity because they restructured my old job. But they were just like, come back anytime.

Kim: Oh, that’s so nice that they were so welcoming.

Melissa: Yeah, it was really an ideal situation. But again, I don’t think I had my head on straight. For sure. It was difficult after the shock of Dave’s death wore off. It was really difficult to concentrate. I decided to not work and then I decided to work. It’s whatever made financial sense for me and my family and what felt comfortable and right and you always have to listen to your gut on that.

That was my situation. I have to say there is not enough bereavement leave. Like three days? C’mon.

Jen: Three days? Yeah, I know. We just had our meeting this last Saturday and one of our members said she had five days.

Kim: Five days of bereavement?

Melissa: Yeah, it’s silly.

Jen: We had the funeral a week later. That’s not even time to have the funeral.

Melissa: Yeah, that policy is kind of ridiculous. But there are other avenues to explore and if you are in a current work situation and you can become really good friends or with your HR department, they can be really helpful in navigating some of those policies.

So that would be something to explore if you’re currently working.

What about you, Kim? What was your work situation?

Crafting a New Path: From Stay-at-Home Mom to Business Owner

Kim: Before Mark got sick, I was a stay-at-home mom. I worked before I had my children, but as soon as my first son was born, I quit working. I was a computer trainer, like a software trainer and an IT technical writer for several years. And that just wasn’t something I could do part time or whatever after my kids were born. So, we decided I’d stay home.

Mark was self-employed and when he got sick, he couldn’t do his job. He basically said, “you need to take over running my business.”  We’ve talked about this before on previous podcasts, but he sold chemicals to the metal processing industry in Detroit, and I knew that because it said that on his business card. Whenever anybody asked me, “what does your husband do?” I would say, “he sells chemicals to the metal processing industry in Detroit,” because that’s what it said on his business card. I didn’t know what that meant exactly, and I wasn’t going to try to explain it to people. Right? So when he got sick, it was like, oh crap, now I need to know what selling chemicals to the metal processing industry actually means.

He’s saying, “you need to take over running the business.” And all this is happening quite fast for us too. Like he was not feeling well. Then he was diagnosed with terminal brain cancer. So, we knew we had to make some quick decisions, and he had to have surgery to remove the tumor and all this stuff was going on. He wanted to give me as much information about how he did things as he could. So, at the time, I’m thinking, okay, all right, I’m going to take over this business. I’m just going to do what he wants me to do. Because I’ve said this before, you don’t tell a dying man no, you just say yes to whatever he wants you to do.

Melissa : Right!

Kim: So, in my mind, I’m thinking sure, I’ll take over running your business, and then I won’t do it anymore. And that was what I thought. I thought I was just going to do this to appease him and get through this horrible year of his countdown to death, and then I would decide what to do after that.

But that’s not quite the way things turned out, because as you’re moving along and going through things, sometimes what you expect to happen or think is going to happen doesn’t, and you have to adjust, right?

So I learned how to run the business while he was still alive. I didn’t know it completely by any stretch of the imagination, but after he died, I thought, okay, well, maybe I’ll just keep doing this for a little bit longer while I’m looking for other work. Like I said, I was a technical writer. I’m like, I can just go get a job doing that somewhere. I don’t really want to do this chemical thing. But it was a flexible schedule so I could come and go as I wanted. And I didn’t realize at the time, right after he died, how incredibly important that was going to be for me and my family.

Speaking of bereavement, I didn’t have any bereavement leave. I did not give myself, as the boss, any time off. I just kept working. I remember my customers were saying, you can take some time. Like, we don’t need these products filled right now. I’m like, “no, your order is coming on Thursday.” This is coming next Tuesday. I got it done. I have to have a plan. I have to have a process. And that was my way to not go insane, okay? For me not to completely implode and go insane. So, I didn’t really have any time off. But again, I had a flexible schedule, so I was not working 60 hours a week. Let me just make that part clear. I thought, well, I don’t want to do this. But it was simple enough to do on maybe a part time basis. I really wasn’t even working full time doing this. So I thought, I’m flexible. I get to be home when I need to for my kids. I get to get them on the bus. I get to get them off the bus. I get to go to their games. I get to go to their teacher conferences. All the things that I had to do this job allowed me to do. So even though in the back of my mind I’m thinking I’m not going to do this for very long, I ended up doing it for eight years. It was just the flexibility that I needed.

Because I was self-employed, I had to get our own insurance, which was highly stressful. And again, I thought I should just go work for somebody else so I can get health care. But sometimes that’s not a viable answer. Just because you can get health care from some other place, or some other job, doesn’t mean that’s the best thing for you. If you’re not flexible, you can’t be home for your kids’ schedules and stuff. So, I didn’t love selling chemicals to the metal processing industry in Detroit, but I did it because I could.

I had to make some of those amends in my own brain because I was telling myself all kinds of stories about how I didn’t know how to do this job. It’s not my forte. Chemistry is definitely not my jam. I was thinking things like, what are you doing? And you’re an imposter, and why are you here? And nobody likes you. They can’t stand to see your face when you walk in the door. I mean, all the really mean things, right? And my customers were like, we love seeing you. And they were so supportive.

You were talking about a second family for you, Jen. I didn’t know these people. They knew me because my husband told them about me, talked about me these all these years, but I didn’t know them. So when I started going in and talking to them and meeting with them, they supported me and brought me in like family, because I knew they thought of Mark as family, so they thought of me as family too. They welcomed me with open arms. I didn’t know how to do the business. They helped me learn along the way too.

There are some really good people out there that will definitely support you if you allow them to. So, if we’re not making crazy stories in our brains and we let people support us, a lot of them will do that for you. So sometimes I think we think we have to do something, we have to go back to work, we have to work in a job that’s eight to five or nine to five. We have to be in this industry. We have to do this thing and we just really don’t. This was not an industry you would have ever convinced me I would have worked in under any circumstances. I mean, I was really convinced I was going to get another job. But I just kept my flexibility, and that was really nice.

There’s a company I would use to look up jobs called FlexJobs. They aggregate a lot of remote and flexible work opportunities. And it’s a great organization. It’s a low, low subscription rate, but they vet all these jobs, and so they’re giving you the best jobs. You can go on job boards and find really crappy jobs or some scams and things like that. Well, FlexJobs doesn’t do that. So I was a FlexJobs subscriber for like two or three years. I would go in and be like, let me look at the writing jobs. And I would look through all of them thinking, yeah, I’m going to apply for this, I’m going to do that. I literally never applied for one job. I kept the subscription, and it was almost like that was a backup for me.

Melissa: A little comforting backup.

Kim: Yes, it was very comforting. It made me feel better that it was there, but I literally never even applied for a job. But I thought I could if I wanted to.

So, I looked at FlexJobs. I looked at Fiverr. It’s an online digital marketplace where you can hire somebody to do a job for you for $5. That’s why they call it Fiverr. And I thought, I could do some proofreading, or I could do some writing. The thought of $5 for my work was a little hard for me to swallow. But you start off at $5, and then you increase your rates as you get more business and more customers. These are just examples of opportunities that you could do. If you don’t like your job, or you don’t want to stay in your job, or you don’t want to be in a nine to five or a corporate position, there are lots of opportunities to be your own boss, to be flexible, or to work remote.

I looked at VIP kid, which is an online tutoring company. I’m like, I could teach English to kids. I could do this, right? So, I had amassed this list of remote and flexible opportunities that I was convinced I was going to do other than the job that I was doing. At one point thought I was going to open an Etsy store, because you could open an Etsy store if you have unique items you want to sell, like jewelry or art. Well, why can’t I sell jewelry? I’ve never made jewelry in my life. But I’m thinking, I don’t want to sell chemicals. Maybe I could sell jewelry. So, I’m like deciding all these things that I could do, but I didn’t do any of them because I didn’t have to. I just kept going in my job. It wasn’t an ideal vocation, but the flexibility was ideal.

Melissa: At some point, you’re kind of building yourself like a safety net with all these options. Oh, I could do Upwork or Fiverr. I’ve got all these skills. I have a safety net if this chemical sales thing doesn’t work out.

Kim: Exactly. I absolutely needed that safety net to know that I could have a backup if I needed it. And I wasn’t sure when I was going to opt out of the chemical business. I just knew that it would be at some point. It took me a very long time to get there. So, like I said, I did it for eight years. Towards the end, maybe like year seven, I’m thinking, I need an exit strategy here. I’m just not sure how to do that because, again, it was my husband’s business. So for me to sell it or to get rid of it was highly emotional and challenging for me because it was his. In my mind, even though he was dead, he was still kind of with me because I was running his business. It was a very difficult transition for me to decide to let go, because I really thought that I would be letting go of his legacy.

But I had to come to the realization that it was not my responsibility to do this forever and ever for him. I did it in the beginning because I’m like, I can’t let go of this business he works so hard for. But at some point, you have to think about you and what’s best for you and not what’s best for everybody else or worry about what everybody else thinks. His parents were even like, “you’re going to sell the business?” I’m like, oh, gosh, what am I doing to them? Because now it’s like I’m feeling guilty, guilty, guilty. And I just felt like Mark would be dying all over again when I finally sold it.  

My point to that is we have enough guilt, right? We widows have enough guilt about any topic, so we don’t need to pour more on ourselves. It’s just that instead of thinking about what’s best for you, we think about what’s best for everybody else. And that’s where we get stuck, and that’s where we start making bad decisions, because we’re thinking about how this affects other people, when really, it’s about how it affects you, which is the major, biggest question you should always be asking. Answering everybody else is secondary.

But I had to get to that point. And it took me eight years to get there, but I finally did. And people were like, “well, aren’t your kids going to take over running the business?”

So, then I had that on top of my head.

Jen: I didn’t even think about that.

Melissa: Well, did they even express interest in wanting to do that?

Kim: No, but it’s almost like a given. You have sons. They’re going to run their father’s business. Some of my customers were like, “well, we could train the boys, or we could help you.” And I’m like, the industry is changing, so that’s a whole other issue. But I thought, I don’t want to make them think that’s something that they had to do.

Jen: Like, introduce that into their heads and think that they have to continue that legacy of their dad.

Kim: No, not at all. Plus the fact that Mark worked with industrial chemicals and he got a brain tumor. The irony was not lost on me. Now, the doctors could never tell us where a brain tumor like Glioblastoma originates. But he worked with industrial chemicals. I don’t want my children working with industrial chemicals. I didn’t even want to work with them. I only went into the plant once a week. I mean, I’m like in and out, like, holding my breath as I’m walking in and whatever. I’m just like, I’m not going to be staying here for a long period of time because I don’t want to expose myself to that. So, no, it really wasn’t an option for my kids. I didn’t want to make that an option for my kids.

Healthcare Considerations: Exploring Options for Widows Returning to Work

Kim: As I’m working, I had to get my own health care. I was self-employed, not part of a group, so I had to buy my own health care. I had a health savings account because I had a high deductible health plan. I’m not sure if you’re aware of the benefits of a health savings account. It’s not like a flexible health account. An HSA is a health savings account. With an HSA, you can roll over your money and save for future healthcare needs. The money that you put into your HSA goes in tax free, and then you pay for medical expenses from it tax free, but it can also grow as an actual investment account, tax free. So, you get a three benefit tax advantage on this, going in, using it and taking it out.

I would only put in a little bit into the health savings account every year. And I don’t know how I found this out or when it ever dawned on me that maxing out your health savings account is a really good idea because it’s such a tax advantaged account and then whatever you put into it lowers your adjusted gross income, so you’re paying less taxes on that money.

The first couple of years I was just putting in a little bit. When I found out about the tax advantage, I called my accountant and I’m like, “what’s going on? Why did I not know this? What’s happening?” And she’s like, “Well, I guess we never really talked about it.” Anyway, I maxed out my HSA from that point on. You can only put a certain amount into your HSA every year, but I would max it and then lower my just gross income. And now I’ve got this little medical nest egg that I’m using for whatever I need. I’m planning to keep it until I hit retirement age. So, when I’m on Medicare and it’s not covering all the things I need it to cover, I can dip into that HSA account because it’s still growing. I’m still investing that money, and it’s still growing.

So when you’re looking at benefits at work and maybe going back to work because you need to have health coverage, that could be true. But there are other options for you to get health care like on Healthcare.gov where you can get subsidies. If you’re not making a certain amount of money, you can get subsidies where the government helps pay for part of your coverage, depending on your financial situation.

A lot of people talk about Cobra. Oh, I have to get Cobra. My husband died. I have to get on Cobra. Cobra is super expensive. It’s your policy, it’s your coverage, but it’s not cheap. And you may actually be better off going on to Healthcare.gov and finding something for yourself even though you’re paying out of pocket. It could be less expensive than Cobra.

Melissa: That’s probably another episode. I’m glad you touched on that because I got a letter after Dave died. He carried our health coverage because in the United States, health care coverage is tied to employment unless you’re over 65 and on Medicare. So, I got this letter, I’m moving, and I’m doing all the things. I get this piece of mail that says your family’s health coverage expires, and you’ve got 30 days to get onto something else. And luckily, I worked. And so I had health coverage through my job. Prior to that, it just made more financial sense to do it through Dave’s work because his coverage was a lot better. But if I wasn’t working, what would I do?

Kim: Well, we should probably do an episode on that because it can be very complicated and emotionally challenging to make those health care decisions. So when you’re thinking about going back to work, sometimes your first consideration is I need health care coverage for your kids or whatever. Sometimes you do need to go back to work for that reason, but it doesn’t mean that you have to go back to the job that you were in.

Melissa: Right? Absolutely.

Kim: You can get a different job, and then you could do what I did and get an HSA. It was like a game for me, any way that I can help myself and avoid paying taxes like everybody else. I can put this money here, and then it lowers this here, and then it grows here. And I’m like, this is genius. Now, just so you know, a high deductible health plan means that my out-of-pocket max was, like, $13,000. Okay? So, I would have had to pay a lot of money to get coverage in order to have this health savings account. But we were healthy. We did not go to the doctor a lot. So, if you’re in a situation where you’re not going to the doctor other than your preventative care or whatever, then an HSA might make sense for you too.

But going back to work is very wrought with a lot of hard decisions because you just don’t know what you need when you’re first widowed. Do you need a ton of coverage? Don’t you? Do you need to be flexible? Can you handle it? Melissa, you thought you could handle going back, and then you figured out that wasn’t going to work for you. Jen, you had your family support at your work, which was what you needed. And I needed the flexibility of just doing whatever I could do, but also being there for my kids when I needed to be.

So it’s hard. It’s really hard to make those decisions on what’s the “best” way. However, you can decide and then change your mind. There are lots and lots of options for flexible and remote work. We’ll put some of those links that we talked about in the show notes.

Wrap Up

Melissa: This is a deep topic. I think we should have another episode.

Jen: I was about to say we can expand on this topic a lot. This is a good one.

Kim: Yeah, I think so too.

Well, then we’ll wrap it up. That’s where our conversation ends on the path back to work post loss. Again, the choice is uniquely personal. It’s shaped by your desires, your needs, and your circumstances. So, whatever you choose, your choice is valid, and we stand by you. If you found some peace or extra support in our words today, or believe that someone else might, would you please pass this episode on?

Until next time, be kind to yourself and know that every step forward is an achievement.