Unemployment Bucket List: how I'm making good use of my time between employed and entrepreneur. Get the full list at The Drowsy Mama.

Unemployment Bucket List

When I decided to go live with my blog a month ahead of schedule, I had pre-written a month worth of posts. I wanted to share with you the strategies I was implementing to make our life keep working when I no longer was. Apparently… life had other plans for me because every single post now seems suddenly irrelevant. More than a few of my plans have changed. I had initially prepared to work from home, take my kids out of daycare and become the frugal penny-pincher we all know I am. Over the past eighteen months, I got an incredible life experience that has helped to shift the way I view my home, my life and the world at large. With some business experience under my belt, I’m approaching everything as business. How do we optimize? Invest? Grow?

Two Big Changes to Plan




I’m making two major investments in my family and my career. The first of which, is the decision to keep my kids in daycare. This is a financially significant investment, to the tune of a few hundred dollars every week. So how do I make this happen? Well, first is fighting for my unemployment benefits. They issued me information on what I’m eligible for but later this week, I have a phone interview to determine if my departure from the company makes me truly eligible. If I am, which I truly believe myself to be, then this is just enough money to keep my kids in daycare. This offers them the stability of maintaining their routine and offers me the time I need to keep working on my business and pursue other opportunities as well.

The second investment very much relies on the first– I’ve decided to return to school. I dropped out of college when I was promoted at work. The demands of parenting and career left little time or energy to finish my associate’s degree. This time investment will allow me to move forward with obtaining a bachelor’s degree– something I had planned on having earned by now– and opens many career doors for me upon its completion. Last week, I settled an old debt with the community college, met with my adviser to confirm I only had 3 classes remaining to graduate and finally, got enrolled. Although I haven’t yet logged in to start the process, I’m already feeling like I’ve accomplished something. So I sat down and had another one of those deep, introspective conversations with myself. What else do I want to accomplish while I’m in that weird place between employee and feeling truly self-employed? So I made what I am calling an unemployment bucket list. The rules for what can make it on the list? It needs to be some form of an investment, optimization or growth. With 26 weeks of available unemployment benefits, here’s my 26 item unemployment bucket list.

The Unemployment Bucket List

Unemployment Bucket List: how I'm making good use of my time between employed and entrepreneur. Get the full list at The Drowsy Mama.




  1. Get my associate’s degree. Get more client testimonials.
  2. Exceed my sales goal for a month.
  3. Sign 10 new clients.
  4. Join a BNI chapter.
  5. Get an office space or co-working membership.
  6. Complete 24 blog posts.
  7. Improve my credit score.
  8. Pay down my credit card debt.
  9. Enroll in a 4-year school.
  10. Get my GPA up to a 3.0+.
  11. Hit 100,000 page views on my blog.
  12. Read 6 books for pleasure.
  13. Find a sport or exercise to get reallllllly into. Maybe bicycling because running sucks. Hush brain. You’re going to offend the runners. Screw the runners. A bike can go faster than their angry mob. Hush brain. Hush.
  14. Get health insurance.
  15. Find a cleaning routine that I can stick with.
  16. Complete Google Analytics Certification.
  17. Complete Google AdWords Certification.
  18. Get Google Partner Certified.
  19. Make peace with my body. Love it or lose it.
  20. Take a vacation.
  21. Clock some volunteer hours.
  22. Launch the resume program. (Details to come!)
  23. Switch to decaf.
  24. Help someone in a big way.
  25. Get a really good job offer.
  26. Every time I cross something off this list, add something new.

So that’s it. That’s the plan. The goals I’ll be chasing for the remainder of year 25. Be sure to check back for progress updates and while you’re here, drop a suggestion in the comments for things to add to my unemployment bucket list as I complete other tasks. 

The Good Fortune of Unemployment: How a fortune cookie changed my career. From The Drowsy Mama.

The Good Fortune of Unemployment

The Good Fortune of Unemployment: How a fortune cookie changed my career. From The Drowsy Mama.

In the rural-ish community where I work  worked just outside the city where I live, there’s one Chinese food restaurant where my boss and I used to grab lunch every month or two. Over time, I’d learned to really look forward to conversations with this man I am lucky to count as both a mentor and a friend. Half the time we’d talk about work, whether that be my position as the Director of Key Accounts or as the entrepreneur behind Carlene Can. The other half, we’d talk about life, the universe and everything. Several months ago, we went to our Chinese spot for lunch. The conversation flowed. We mixed and matched our plates to get a little bit of everything and we, as always, enjoyed each other’s company. The only thing that had changed was, well, the company.

The First Cookie

Back in January, I learned a bit prematurely that our five-location franchise was being sold to a new owner. Eventually, Bill, my then-boss, told the rest of the staff, we met the new owner and the paperwork closed. At this one particular lunch at Yu’s, it was still our little secret. And in that secret, he knew I was terrified of the change that was coming. Despite his reassuring that this was going to be a wonderful thing for us, I was still anxious. I made it a point to apply to jobs regularly, interviewed a couple of times a month and probably turned down as many job offers as there were companies who decided to “go with another candidate.” Nothing was quite the right fit. We touched on my interest in keeping doors open for myself but as always, he was reassuring that everything was going to work out in the wash.

As our lunch came to a close, we both selected our fortune cookies from the check. I couldn’t tell you what his said but I know as clear as my children’s birthdays exactly what mine told me:

“Trust your gut in the coming days.”

"Trust your gut in the coming days." The Good Fortune of Unemployment: How a fortune cookie changed my career. From The Drowsy Mama.




Wow. I usually don’t put much credence in silly little fortune cookies but this one just hit a nerve. So I slipped it into the clear plastic cover of my half-sized binder/planner to keep it as a clear and present reminder. Trust your gut. Trust it! But I have an awful gut! If there’s anything I’ve learned from years of impulsive teenage and early adulthood decisions, if there’s one thing NOT to do, it’s trust your gut. But apparently it was time to get over myself and learn to accept that my instincts are good ones.

Over the next several weeks, the phrase “trust your gut” kept coming up. Over and over with different people who never saw my planner or heard about my silly fortune cookie. Maybe it was just another case of being acutely aware of something as soon as you’re exposed, like pregnant women noticing other pregnant women, but to me it was a regular affirmation of what I already knew to be true. It was time to heal and learn to believe in myself again.

The Second Cookie

Friday, July 15 was my last Friday at work. I had been given four weeks notice after the sale closed and had failed to find another job before I was notified of this fact. Four weeks had gone much faster than expected on the job hunt front and I was still without a viable full-time position– even one that would require a pay cut. To celebrate this final Friday, so to speak, Izzy came to the country to take me out for Chinese food at my work spot. We enjoyed good conversation, good food and when our lunch came to a close, good fortune cookies.

Over the preceding several weeks, we had come to the decision together that it may be a good idea to use this period of unemployment to really push full speed ahead with my small digital marketing company. Without 40+ hours a week dedicated to selling for a different business, I would have the time to go sell for myself and service my own clients. Entrepreneurship is terrifying to me but, as they say, no risk, no reward. The sleepless nights, stomach aches and truthfully, moderate depression symptoms have been taking a toll on me, and this is only the beginning. Maybe this isn’t for me. Maybe I need to stop tinkering with all of the back end work of running a business and dedicate those hours to filling out applications and sending off my resume. Maybe I’m not cut out for this.

I hadn’t had Chinese food since that lunch with Bill. I held my unopened fortune cookie in my hand as I told the story of “trust your gut” to Izzy, my hand fiercely clutching it, as if to will a good follow-up onto the paper inside. I broke it open,

“You are heading in the right direction.”

"You are heading in the right direction." The Good Fortune of Unemployment: How a fortune cookie changed my career. From The Drowsy Mama.

This. This was exactly the fortune I needed. Vague as it might have been, in the context of everything, positively everything happening with me, this fortune was exactly perfect.




"You are heading in the right direction." "Trust your gut in the coming days." The Good Fortune of Unemployment: How a fortune cookie changed my career. From The Drowsy Mama.

The Drowsy Mama is back after an eighteen-month hiatus. I hope you’ll come back to follow my journey with entrepreneurship, motherhood and how I’m applying some of the great business skills I’ve learned to running a household. Please subscribe to get updates on new posts as they publish and feel free to comment with your own experiences and feedback.