AAAAHHH!!!! (Image by Matt Groening of The Simpsons fame/

Ever since I’ve decided to go freelance, I’ve been stricken with fear wondering whether I’m doing the right thing, doing it at the right time, or going at it with the right intentions.  The reptilian brain in me is saying no no no no


. . . and about 5 years ago, the highly un-confident, stricken with doubt me would have wholeheartedly agreed, dropped this precarious gamble and stuck to a stable but hum-drum life.  Now, I’m only slightly un-confident, burdened with skepticism, and trying to rationalize what could well be a significantly life-changing move on my part.  I just recently went through another significantly live changing event which I can sum up with this expression . . .

Cool. What do I do now? Hope I don’t ask the same question in about 3 months or so.








After I retired, or rather, towards the last days of my impending retirement, I intended on trying to get into an internship because I thought that would be a decent way of easing myself into the civilian workforce. However, I went about it in the most buckshot fashion I could think of. I applied to…

1. Capital Public Radio

2. Entercom


4. ABC

5. CBS

They were all jobs that fit with what I thought I wanted to do, to work in Public Radio (NPR, APM and their local affiliates) and network TV. (less on the reality shows and more on the newsroom) .  I should have stopped there, but instead I went full death blossom. (for all of you that don’t know what I mean by “death blossom…)

via GIPHY#death #blossom

So I also sent applications to…

6. Anheuser Bush – because brewery tour guide sounded really cool, except when you take their stupid timed survey and get blackballed if you don’t complete it in time . . . dicks.

7. Johnson & Johnson – not just a pharmaceutical company, but also a corporation with goals to guide and develop the leaders of tomorrow.  I apparently was not part of that goal.

8. Aramark – does anybody outside of the military know these guys?  I did, and I thought my being a veteran was a shoe-in.  Boy was I wrong.

9. Visit California – to my California residents, remember their commercials that featured Arnold Schwarzenegger when he was governor at the time,

      1. Yeah these guys. I wanted to work for these guys. #whatthehellwasithinking.

10. CDW – an IT company I had no reason to be interested in, except I was despera . . . I mean determined.

11. The State Compensation Insurance Fund or SCIF, a quasi-nonprofit insurance firm where I neeeeeever would have thought to work for, but when times are tough I supposed.

All these places were offering internships and student assistant jobs in public relations, marketing and sales, which all involved customer service – something I vowed never to get back into…EVER!

NOTE #1:  Now I’m not saying it’s beneath me.  It’s not.  I give props to anybody and everybody who has the tenacity to attract customers and close sales.  It’s just not my thing is all.

via GIPHY #reallythough #onthereals


And because I was so desper . . . I mean eager, I sent resumes and cover letters to…

12. UC Davis

13. Sacramento State University

14.  Los Rios Community College

15.  Solano Community College

Because I really wanted to embrace my past narrative of “supporting educational institutions who educate and inform our communities,” as an administrative assistant, which basically code for secretary!

NOTE #2:  Again, I do not mean to disparage or demean this line of work.  Admin is more than filing papers, taking phone calls, making coffee and picking up the boss’ dry cleaning, as is stereotyped in movies and television.  Again, it’s not my cup of tea ok?


However, after I had done so much grunt work on the job search front that I discovered a flaw in my approach.  But first some context.

I attended what was called the Senior Executive Workforce Transition Workshop, a 3 day course that helped prepare high-ranking, executive level personnel to continue their career outside of the military, or at least that how it was advertised.  There, I thought I learned innovate ways of finding, applying, and securing jobs, or at least I seemed like it to someone who hasn’t had to find, apply and interview for a job in 20+ years.  I was really entranced by how this workshop touted this “under-utilized” website that guides you step-by-step on how to write great cover letters and resumes.  And sure enough, I paid the subscription fee, used it to churn out a “variety” of cover letters and resumes and sent them to all the organizations I just mentioned.

Out of the 20 cover letters and resumes I sent, I got 3 calls for a phone interview.  Out of those 3 interviews, I got one offer, from my last preferred employer, the SCIF.  Was I really that desperate (yes, desperate) enough to take the job?  If I did, I’d be working there now and probably be blogging about how this is too much like my old job, except without the uniform, the breakneck ops tempo and the looooong hours.

Then I saw an eye-opening, Linkedin endorsed video of a recruitment coach by the name of J.T. O’Donnell who had newer and better career searching concepts in Work It Daily.  It was there that I found out . . .

  1. My shotgun method of “applying” for jobs sucked
  2. My methods of writing cover letters and resumes sucked
  3. The website I used to write those resumes and cover letters didn’t necessarily suck, but the way I used it did

Basically, I thought I was clever by cutting and pasting the website‘s canned statements to write my professional summary, work experience, and additional information.  I thought that was what tailoring meant and I could do that for any job.  I thought wrong.

So, here I am now blogging about how I screwed up my whole job finding process and didn’t course correct until it was too late.

But was it too late?  Technically it isn’t.  I can still resume my job hunt using the lessons I learned from Work It Daily.  But it was around the time I got the rejection from CAP Radio (for a Marketing internship no less) and the SCIF job offer I turned down that I went into introspection mode, questioning whether I wanted to go back to the 9 to 5 again.  My rational brain scoffed and said. “What are you crazy?  Yeah!  It’s a stable job with a stable paycheck that can greatly supplement your current pension.  Why wouldn’t you go back to tried and true?”  Then I remembered Ms. O’Donnell’s tips on choosing the right career…

She basically asked, “What type of a role is work going to play in your life story?”  Did I want it to play a supporting role, the lead role, or the whole movie? (start the video at 1:03 if you want to know what I’m talking about) I thought about it, and I categorized all my past and possible future roles like this:

Job Secretary (lol) Brewery Tour Guide Sales Rep Marketing Rep
Career Aircraft Mechanic Cryptologic Linguist Management Consultant
Calling Writer

Then it hit me.  The voice in my head that that sang my love for stories and writing never stopped.  The volume’s been turned down for quite a while, but it was always in the background whispering…hypnotizing…enticing…



Or maybe that’s just delusion guiding me to ruin.  Whatever the case, I was convinced to pursue my calling as a writer.  And to complicate things even more, I’ve decided to become a freelancer writer!


Time will tell if this is another phase, (because this isn’t the first time this happened, a story to be told at a later time) but I really don’t want it to be.  I’m aware of the uncertainty and risks associated with this calling, or at least I think I am.  I suppose all I can do is stay frosty and continue along this path, and rebrand myself as the eponymous Sugar Freelancer!!



P.S. It is not lost on me that freelancing also requires skills in public relations, marketing and sales, all of which involve customer service, as well as organization communication and *sigh* customer relations, all of which involve administrative work.


Real supportive Mr. The Most Interesting Man in the World.