Finding Happiness in Self-Employment: A Postal Employee Goes Rogue…in a good way

This is a guest post by  Jennifer Monahan. Jennifer was kind enough to share with me her experiences in creating an ideal career for herself despite the uncertainty and risks that go with it. It’s stories like these that reflect the core of this website’s theme. If you have such a story to share, please don’t hesitate to contact me. Our readers would love to hear it.

I am a 16 year postal veteran.  For years, I worked behind the counter selling stamps in a small Florida town.  Who knows, I may have sold a postcard stamp to you or someone you know who was on vacation in the Sunshine State.

All those years I was selling stamps, I was looking for a new career, because I knew I wasn’t a “lifer”  in government work.  I was not going to put in 30 years and retire.  That’s what’s known as a delayed life plan, and I wanted nothing to do with it.  The photo of the lemonade stand on Kenji’s blog, Unready and Willing, looks just like the stand I set up when I was ten years old.  The photo sums up who I am, an entrepreneur at heart.

I’ve always had the drive and determination to work for myself, but it took years to figure out what that career would look like.   The long search was worth it.  I got answers and finally made a move.  It was a scary leap of faith to leave behind the benefits of a steady paycheck, paid vacations, health care, and sick leave, but I dropped the “golden handcuffs”  of a government job and became a freelance bookkeeper (Talk about being Unready and Willing!).  My motive to jump into self employment was to work when I wanted to and take time off when I needed it most.

How did I do it?  I asked myself the following questions:

  • What service can offer the community?
  • What am I already good at?
  • What do I already know how to do?
  • What am I genuinely interested in?

And then I listened and watched for the answers.

Through the years, I was learning about personal finance and investments to benefit my own financial situation.  I read books, publications, and attended those free seminars that accountants, stock brokers, and lawyers give to educate the public about investments, wills, trusts, and estate planning.  I applied what I learned to my own life with great success which gave me the confidence to share what I had learned with the community.

The first clue into my new career was revealed to me when a postal customer came to my counter and said, “My husband just died, and I don’t know how to handle the finances.  I have these stock certificates to send in (mailing them registered mail) and I don’t know what I’m doing.” In that moment, I realized I had  something of value to add to the lives of others.  I decided to become a private bookkeeper to the elderly.    My personal interests matched their personal needs, and I could help them get through a difficult time in their lives.

Eighteen months into my new career, things worked out so well, I took a two month trip to Australia over the turn of the millennium.  While on vacation, I kept a daily journal for the sole purpose of being able to revisit the journey long after the memories faded.

This journal soon turned into an outline for my first book, An American in Oz, and helped me segue into a career as an author.   My interests had moved beyond numbers, and friends and family suggested I write about my experience in the land downunder.  It was an idea I took seriously because: a) I love to write.  It’s something I’m already interested in, and b) I could reach a wider audience and experience another level of freedom as a published author.

Oftentimes, the answer to our deepest longing (What do I really want?) is right in front of us, so close we cannot see it, but when recognized, lives change.

An American in Oz was released on Australia Day 2010, January 26th, and I no longer work as a freelance bookkeeper.  Additional career opportunities are opening up now that the book is finished, and a wide range of groups are asking me to speak about careers, the writing process, and, of course, Australia.   Quitting my job at the post office was one of the best decisions I ever made.  Joining several years ago was another good choice.  It helped me prepare for the speaking side of being a writer.  I continue to share what I’ve learned along the way, and while the subjects may change, the core desire to reach out remains the same.

I might have been Unready and Willing when I left the 9-5, but taking a leap of faith was the only direction to go.  Finding work that fulfills us is one of life’s greatest rewards.  I’ve come a long way from selling stamps, and every step led to where I am today.

Wherever you are in life, fellow adventurers, follow your hunches, trust your ideas, and recognize the answers when they show up.  They always do.  Continue to grow and learn and to find what makes you happy at every stage of life.  You have a destiny that is great!  And that’s the Truth with a capital T.

Jennifer Monahan: Author and Adventurer

To read more about how Jennifer transitioned from government employee to freelance bookkeeper, go to Her story is told in the 11-page Introduction of the book An American in Oz: Discovering the Island Continent of Australia.  You can download the Introduction for free on her website.  No strings attached and no email address required.

If you’ve always wanted to go to Australia or know someone who does, check out (The photo of the outback is worth the visit.)  An American in Oz is all about Australia from an American perspective and an intimate look at the largest island continent in the world.  It’s also a story about trusting life to unfold one day at a time through a “no plan” plan, because setting goals can be highly overrated.

You can also follow Jennifer on her blog at

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  • Wow, thank you for sharing that Jennifer. Normally I would ask someone how they had the courage to do something like that but it’s obvious that there’s no magic secret. It’s scary for everyone and you just have to acknowledge and move on in spite of the fear.

    Thank you,
    .-= Ben Weston´s last blog ..Introversion 101 =-.

  • I’m new here and couldn’t have found a better post to read, thanks Jennifer. I’m realizing that the time will never be better. What am I going to do? Stick for another two years to save more money? It’s obvious that I can’t stand another two weeks here, let alone two years.

    I’m a bit scared though!
    .-= Moon Hussain´s last blog ..Clash Of The Titans: Pros & Cons of Various Types Of Passive Income Streams =-.

  • Everything that we need to achieve our dreams is within us. With the right attitude and taking responsibility for our choice, we can achieve anything we aspire. 🙂

  • This is great, poignantly told advice Jennifer! It made me reflect on my own “stamp selling” days ages ago only to reinforce our shared philosophy that life is nothing if you can’t weave your own dreams. Transitioning into professional and creative freedom is scary and tricky business, but hearing your story and stories like it are truly inspiring!