May 04 2011
My 36 Jobs – The Secret Art of Choosing Well (and it’s not always wisely)
WRITTEN by,
When I was a kid, I was quite the entrepreneur.
I’d dream up businesses, everyone different and unique. Weeks would go into my businesses plans. How I’d find clients, my rates, who would need my services. Along with sending letters to country singers and drawing out floor plans for my houses in the sky, this was one of my favorite activities.
Alas, even as a child, the world held its sway. I was told I had to spend money to make money. And I had a big $0. Time to get a real job working for someone else.
I started working when I was 12. It didn’t take me long to realize how much working for other people sucked.
Thus, I learned to game the system. I compiled for you a list of (I’m pretty sure) every job I have ever had. This list groups all of the freelance gigs in their respected areas, and it doesn’t count long term volunteer positions.
- 1. Babysitter <- 8 years worth. I was enamored with The Babysitter’s Club series.
2. Lemonade stand operator <- You would count this if you saw me as a kid. I trained my siblings to look sad when people walked by to make it look like we hadn’t made any money. I’m much more ethical these days.
3. Yard worker
4. Singer – freelance
5. Barista
6. Coffee Cart Manager
7. Janitor
8. Janitor <- Great gig. Sweeping and mopping AND I got to sing at the top of my lungs in the church sanctuary.
9. Clothing Retail
10. Receptionist
11. Barista
12. Waitress
13. Starbucks Round 1
14. Call center worker
15. Model – freelance <- Did an in-house ad for Clear Wireless, plus some other work.
16. Promo girl – freelance
17. Starbucks Round 2
18. Waitress <- Like Hooter’s, but no rules. I made it two weeks and couldn’t handle it anymore. On the other hand, I made enough to pay my rent for months in advance.
19. Pizza Prep
20. Pizza Prep
21. Barista <- My job of 8 months. Got paid to dress cute and occasionally make someone coffee. Mostly, I just flirted with men (and women) in uniform all day. (Mr. Germany – I miss you and your cute butt.)
22. Barista
23. Barista
24. Starbucks Round 3 <- They just don’t learn, do they?
25. Gap
26. Bar promos
27. Sales
28. Extras work <- You can see me in Leverage, Brain Trust, and Extraordinary Measures.
29. Site coordinator
30. Cocktail waitress <- Three days of crazy, sexy strange.
31. Barista
32. Assistant Director
33. Sales
34. Consignment Store
35. Acting gigs
And finally my current job…
36. Writer, branding diva, and entrepreneur
Why on earth would I share this? It’s a testament to my obvious commitment issues, flighty tendencies, and fleeting passions.
It’s also a picture of my insatiable, passion nature. It shows you I can get hired by anyone, anywhere – even if I start as unqualified. It shows I hit the top of the learning curve in a very short period of time – and then I make the decision to stay or not.
I spent a day to a week at most of these jobs. The longest I stayed anywhere? 8 months.
The places I chose to stay longest had the most interesting people. Happy people. I was encouraged to act as much myself as possible. My ingenuity and creativity were valued.
And yet, most people would look at this list and promptly whip their heads around to stare at me like I was insane. And for those people, I have a question.
Is it crazier to pursue happiness or security?
I have a question for you, too.
Has anyone ever told you that you are in control, darling?
Think of decisions as the universe’s gift to you. Your decisions are yours.
Including your decision to dedicate yourself to finding work so meaningful, it makes your heart want to burst.
Your decision to live life on your terms.
Your decision to play by a different set of rules. Here is a quick set to get you started, if you’re lost.
How you can game the system:
- 1. Determine what it is you need in a job for it to make you happy (ignore the $$$ here).
Do you need to express your creativity? Is order necessary? Is a team environment conducive to your growth? Know your idiosyncrasies. They are now your list of requirements for a job.
2. Decide if your job makes you light up.
If not, start looking for something that does. (This is how you nail the interview, by the way. You can’t fake real passion. And everyone wants the passion on their team.)
3. Flip the system the bird.
If you know what makes you tick, you can make it happen on your own terms. Moonlight a bit. Watch the magic unfold.
Tricks and tips:
- False security is a gateway drug to settling. Your job – and likely sole source of income – is false security.
- Find a mentor and friends who get it so at least a few people don’t look at you like you’re psychotic. (You’re not.)
- Never, ever sacrifice your happiness for a paycheck. It’s better to scrounge for change in the couch than to do something that is sucking out your soul.
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29 Comments




great message. i am 54 yrs old and finally have discovered this for myself recently. getting ready to make a big move across the country and give it a go in a place i’d rather be than where i am “expected” to be. i now feel fearless and ready to do it my way.
not disrespecting anyone , not even myself. great post ! thanks
That’s great, Jan! You rock! It’s never about disrespecting anyone – or at least it isn’t if it is authentic – it’s about doing what is right for you.
I’ve had quite a few jobs ranging from retail and education, to real estate, tax preparation, and healthcare. I’ve learned something valuable from each one.
I like how you mentioned finding other people who get it. I did that recently, and whaddya know? I ended up with a business partner. Now I have control in shaping something that resembles me without being asked to keep my head down and do what I’m told. It’s marvelous.
Thanks for sharing, Dusti. Undefinable You is going to rock the pants off people. I’m gonna go find my pants now.
Haha! Thanks, Angel. What a killer way to find a business partner!
P.S. to everyone else – Find someone to collab with. It’ll revolutionize your project!
Love it! I just quit my “job that pays the bills” to do the jobs that “someday will pay the bills” (I’m a violinist…) I figure, if we’re willing to downsize our income to do the things we love, we probably have the determination and passion to make the things we love boost that income right back up! And if not… we’re still doing the things we love, which means we’ve pretty much won the battle
Congratulations!!! I love hearing about when people kill their day jobs, and you totally have the right mind set. Do what you love, and rock it, girl!
I like the direction you are going! This is great.
Hi Dusty.
The best way to look at that long list of job changes is to see it as “feeling the water”. You were trying out different types of work to see what you felt was on your path. The experience, growth and wisdom gained from constant change is acquired at a much faster pace than by staying still
David.
It’s true. I have no regrets about the choices I made regarding these nowhere jobs. They weren’t right for me, and if I wouldn’t have set my work life on fast forward, I might not have known!
Love the line, “False security is a gateway drug to settling.” My best friend has told me, over & over, in love & in life: “Cari, don’t settle.” I think it’s the most empowering advice anyone has ever given me…and I appreciate how you link settling to false security.
I’ve also been mulling over all my past jobs, and coming to a lot of the same conclusions!
Thanks, Caroline! False security is our numero uno enemy! We shall vanquish him together!
“Find a mentor and friends who get it so at least a few people don’t look at you like you’re psychotic. (You’re not.)”
I love that you mentioned this because it is what Im currently doing as I transition into going for my passion (photography) and leaving my day job. I meet with friends who went for their passion and started their own business, to gain more insights and of course feel more encouraged
Networking with people who actually get it soooo important! I had to kick a lot of not-really-friends to the curb because they couldn’t stand behind what I was doing. No bueno!
Woa-just for fun I wrote mine out (jobs) and I have 20 (21 if you count yearly yard sale person) no counting volunteering! Holy crap! lol-remember when we said how similar we were?
Anyways, thanks for the post. It’s a great pep talk with some awesome real life ways to work out what you want to do. And it reinforced a decision I made recently that was tough financially. Again, thank you.
Nice Dawn! Haha, we win.
I absolutely love this post, Dusti. Yet again, you’ve touched upon the fragmented events in our so-called lives that makes up reality … yet this reality makes us who we are today and who we shall become tomorrow.
Your strength, wisdom and inner determination to MAKE life work is admirable — despite challenges, circumstances and situations beyond our control. Bravo to you, dear friend!
Thanks, Nina! I cannot WAIT to catch and hear your stories, homegirl!
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Great article!
I’m at uni and everyday for years there’s been the same messages given to me of panic to find a “stable career” with a weekly paycheck like your future depends on it. Everyone said I should be a lawyer, but I found out the hard way that wasn’t what I wanted. This article just makes me feel a lot better; even though I have no idea what I want to do I will take these pointers and have faith that if I put happiness first something great will come.
Fiona
I love this post! It inspired me to count up my jobs. I have 20 so far (but didn’t count any that lasted less than a week!). Pretty soon I’ll be able to put “Writer” on the list, and I’m pumped about that.
Fabulous! I totally count everything, lol. Most of them lasted less than a week. I think it’s fun to see what all you considered doing, though. Congrats on your latest and greatest title!
^.^ thank you Dusti …I grew up hearing how wrong it was of me to be “so fickle” & “unstable” (screw THAT!) …and recently was told that I have “no real experience or qualifications” because I’ve “never held down a job for an extended period of time” -to which I responded:
“uh, correction: there simply never has been a particular employer that has been able to buy or keep me …I’m infinitely priceless -and I’m not referring to monetary compensation issues, either” ^.~ and I MEANT it.
…it felt SOOOOOOOO good!
…thank you Dusti!
You & what you offer here Dusti are an inspiration
Right?! No real qualifications my ass! There is a ton of value in being able to instantly pick up whatever you do.
Infinitely priceless… I have a feeling you and I will get along magnificently!
^.^ agreed!
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A number of years ago someone told me that the average person changes careers 11 times before it’s over and I responded, “Is that all?” I can relate to everything you wrote, even the expletives, as I am a “passionate” person motivated by happiness not a paycheck, too. The best job I ever had was being a mom but the baby is soon off to college, the husband’s unemployed, still, and I find myself once again working for a paranoid, micromanager in a small family-run business that’s not my own. Damn. Guess it’s time to make some changes again, and thanks for your words. I enjoyed reading them.
I’m glad I’m not the only one! I had roughly 45 jobs by the time I turned 20 and now over 60 jobs at age 28. My last 3 years are the most tame as I now work online but man, what an experience.
Glad there are more like us out there!
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