Quit Week: The Email That Got Me Four Freelance Offers from Serena Manna

Exiting a job gracefully can be one of the hardest parts of any job transition. Below is a fantastic example of a goodbye email that was widely-sent yet has an extremely personal touch, written by my former client, Serena.

I had met Serena once or twice virtually & briefly before I received this email. Her message impressed me so much that I reached out to hire her for contract work supporting Penney Leadership communications. Turns out, I wasn't the only one she impressed—a few other entrepreneurs reached out to secure her services as well.

In short, you never know what doors a message like this might open!

Serena was so generous to not only share her email template with us, but also the full story of her job transition.

She dives into how she handled the guilt associated with leaving, strengthened the connections she was worried about losing, and actually improved her sense of self in the process:


Leaving a job, especially a job that I loved, was challenging.

Just like anything transitional, a season change or a shift in how I value myself, I thought of quitting as a part of a bigger process - a process that reminded me of my own value and what I valued in a career.

When I first started having thoughts about leaving my job my mind went right to the people that I would be letting down, the programs that might not happen anymore, the risk that I would be taking (having nothing lined up), and the linear career trajectory that I was ‘interrupting.’

To paint a picture: It was September of last year, seasons changing, the pandemic at peak uncertainty, and my grant-funded contract at a small-business development center coming to an end with the option to extend for another year. 

I loved the work, the skills that I was learning, and the people that I worked with, however the pay made it challenging to support myself and the energy of the world was just as chaotic as the decisions that I felt faced with.

Basically, I felt guilty and discouraged.

And while I knew it was natural to feel guilty about leaving, I also knew that my guilt was what would hold me back from honoring my own needs.

When I feel guilty it tends to overpower any other feeling, like my excitement for future opportunities, and then I make decisions based on how others will feel. 

And while thinking of others and being empathetic was rewarding, useful, and how I made strong connections, in terms of decisions for my future it cast a blind spot on my own value.

I felt torn and I needed to shift my mindset to make a decision that was best for me. And sometimes that’s the hardest part: taking ownership of what’s best for yourself at a given time.

When I think back to that time the word ownership and owning my needs surfaces because for the first time I recognized that asking for what I truly wanted was scary because I believed it would be met with resistance - and I liked the path of least resistance, right?

I used to believe that the best decisions for me were the ones that were met with the least resistance - if everyone was happy with me that signified that I was doing a ‘good’ job. 

But thinking that everyone should always be happy with me wasn’t very realistic, especially when work is involved.  

My gut was telling me that I was worth more, that I needed to make a shift, and communicate what I was feeling. 

Before making my decision to leave I asked leadership about the role and the amount that I needed to be compensated for in order to live comfortably. 

While I felt valued in my position I needed my compensation to reflect that too. 

And I knew the communication could be done in a way that honored the place that I worked for, the people that I worked with, and the talents that I was developing.

I thought of the people that I worked with and how much I learned from them just through our conversations. 

The people who came to the small-business development center for support were fascinating to speak to. They connected who they were with what they got paid to do and they activated the parts of me that I totally forgot were there. 

The parts of me that wanted to create, self-express, and write.

At times, I was using these skills in my role by creating visibility for small business owners in the community - interviewing them and then publishing their stories in our monthly Q+As. 

In those conversations that I facilitated I saw people’s full-self come out and I can’t explain why but I felt like I had something to do with the person being able to open up.

So there I was, at the end of my term, with a clearer idea of how I wanted to support entrepreneurs and I recognized that I wouldn’t be able to develop those talents in my current day-to-day responsibilities. 

In the spirit of all the people that I connected with over the two years who brought their full-selves, I decided to bring my full-self when making the decision to stay or to go. 

And that meant that I couldn’t let the guilt for leaving cast a shadow on all I had accomplished in my term there. 

Over the course of two years I had celebrated some big wins with entrepreneurs in the community, with the teams I worked with there, and everyone in between.  

Here’s the most important things that I did to make leaving my job an easier process:

  • I remembered that in my connection to a role that I once felt perfect for, it had done its job for me: The grant-funded position advertised as a ‘skill-building opportunity’ helped me identify my own talents in various personal development opportunities.

  • I hired a career coach to help me facilitate the process of owning and communicating my talents. 

  • I communicated my appreciation to those who inspired me and I sent a goodbye email to the people that I had a meaningful conversation with –> This email language would later prompt four freelance offers. (shown below)

  • I wrote an email to the team and the board about the big wins that the community and I celebrated with and then named exactly the field that I was looking for and that my young twenty-four year old self would boldly take a leadership position.

Along with the reassuring shifts in thinking I still worried. I worried about the connections that I would lose: My connection to a role that I once felt perfect for and connections to those that I worked with in many different capacities.

I got clear on why those connections meant so much to me.

My natural curiosity for what entrepreneurs were experiencing kept my  spirits up during an uncertain period (still uncertain at times) and when people asked what I did I responded with: “I’m currently looking for my next move but I sure do know what I’m interested in.” 

And that typically sparked many genuine and inspiring conversations - just like the ones I had when I was working at the small business development center. 

All the parts of me that I enjoyed using in my role weren't going anywhere, in fact this leap would only strengthen them, even in the most painful moments that a risky decision brings. 

The goodbye email that got me four freelance offers: 

Hi there,

If you're receiving this, it's because you made my time at Social Enterprise Greenhouse memorable. I wanted to share a brief update: My VISTA contract at SEG ended last Wednesday & I am actively looking for something new! My search is typically guided by keywords specific to food access & regenerative food systems (trying for a leadership position at an organization) while finishing my Sustainable Economic Development graduate program. I will be in the Providence area indefinitely (love it here).

Each one of you taught me something or were extraordinarily helpful during my time working in the social enterprise field. As I continue professionally I constantly ask myself what actually defines a social enterprise and where my skills fit in helping others understand what social impact means. Thanks for believing in the importance of supporting local businesses and helping others learn new tools to make their dreams a reality.

You can reach me at my personal email with any future inquiries and I wish you all the best!

Kindly,
Serena

Carole-Ann Penney, Founder

As a Career Strategist and Founder of Penney Leadership, I help mission-driven leaders navigate their work and lives with purpose and resilience.

http://www.penneyleadership.com
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Quit Week: How to Take Care of Yourself in a Job Transition

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#CareerDiaries: Quitting Doesn't Make You a Quitter