travel, marketing & entrepreneurship

Experiments in Lifestyle Design: All the Jobs You’ve Ever Had

Published: January 5th, 2010

Lemonade Stand

What do you want to be when you grow up?

At age seven, the answer was easy. I was a dreamer. I want to be an archaeologist! I want to wear a cool hat and creep through cramped tunnels! I want to chase bad guys and speak funny languages and eat monkey brain soup! You should have seen me, digging through my school’s playground, claiming strange rocks as fossils, my hands caked in dirt, knees colored brown.

Back then it wasn’t about money. It was about the important things. The lifestyle, adventure and mystery. What invigorated me. What made me feel…alive. Naturally, of course, as I grew older what I wanted to be became harder and harder to define. I made things complicated. I thought about careers and money and having to save up vacation days. This whole growing up thing was serious business. Where would I fit in?

People generate income in all kinds of ways

It wasn’t until recently that I realized something. It’s not about fitting in. People grow up in all kinds of ways. They become doctors and lawyers, poker players and public speakers. Some work one job, others have several streams of income. Some travel, others stay put.

In a post-New Years effort to realign myself and think about the future, I participated in a fun exercise. I thought about all the jobs I have ever had. Maybe, by tracing through my income history I can get a better sense of where to head next.

Early Years
Age 6 – sold origami fortune tellers and paper airplanes for $.05 and $.10 [was stopped by teacher after two days]
Age 8 – sold lemonade with my friend Price
Age 12 – exploited a loophole with AllAdvantage, a short-lived infomediary company and made $200 before canceling my account

High School and College
Maggie Moos – scooped ice cream part-time for one year
The Temple Religious School – helped teach kindergarten once a week
Valet Parking – for a month [they found out I didn't know how to drive stick]
Cutting Onions – a one-night gig for $100, chopping onions for four hours [I was scammed and never paid]
Carraba’s – hosted at an Italian restaurant for a summer
O’Charley’s – served at an American restaurant another summer
Online Poker – FAIL.
Kaplan – taught an SAT prep class and did private tutoring and exam proctoring
KROLL – interned at a background screening company and worked on a data mining project for a summer

Startup Years
homeWUrk – co-founded an e-commerce site (now defunct) for dorm room products, targeted at incoming out-of-state freshmen
Moving Off Campus – helped populate city data into their back-end system

What I’m Doing Now
AIRINC – cost-of-living research for a global consulting firm
Nepal Prints – selling photography for charity

What interesting things have you done to earn income? Do you find this exercise helpful?

image credit to kapgar


8 Comments on “Experiments in Lifestyle Design: All the Jobs You’ve Ever Had”

  1. 1 Nate said at 9:25 am on January 6th, 2010:

    What a fun exercise, you’ve done some interesting things! I’m going to have to do this on my own and see what kind of stuff I can remember. Growing up on a farm, most of my work was very labor intensive, like I hauled rocks out of my family’s huge garden for a whole summer. That was a blast (sarcasm).
    .-= Nate´s last blog ..low-budget content creation experiment =-.

  2. 2 Alan said at 2:48 pm on January 7th, 2010:

    @Nate You grew up on a farm? Very cool. My mom’s family is from rural Indiana, but instead of helping out on the farm I would shoot model rockets into the corn field…and then spend the better part of the afternoon hunting them down.
    .-= Alan´s last blog ..Experiments in Lifestyle Design: All the Jobs You’ve Ever Had =-.

  3. 3 Nomadic Matt said at 11:33 pm on January 7th, 2010:

    I worked at Family Dollar and Dominoes
    .-= Nomadic Matt´s last blog ..A Look at Maori Culture =-.

  4. 4 flip said at 6:07 am on January 8th, 2010:

    i sold weird things when i was in grade school :-)
    .-= flip´s last blog ..Convince Me to Go to India =-.

  5. 5 Robert said at 1:00 am on January 9th, 2010:

    What a cool exercise. Completely valuable for inspiration and perspective. Here are mine but narrowed down to entrepreneur efforts. Had some from doing this a while back heh, sorry for the length!

    6th grade. i traced ninja turtle bookmarks and sold them at for $1 until the MAN (teachers) shut me down.
    highschool pyramid surf the web with a banner for time scheme, made $3000 one month!
    ING savings push, brought in about $300 in highschool savings account sign ups
    eutrader.org, college ebay (article)
    ebay dropshipping, thousands…until I realized the shirts were fake
    granholm design and development web design, lots of work, money though
    california pet sitters…pet sitting?
    surside tech support, got some clients, made some money, never went legit…didn’t market it
    independent freelancing, same as granholm design and development. again, more work, fun but lots of work.
    garage sales + mapping + ebay. still me doing grunt work, but making money when selling garage sale stuff
    spinningclocks.com collaborative popular culture blog, made 72 cents on ads (june 2009)
    hotandrelevant.com – whats hot on the web, aggregation for hits and ads, never put more effort into this, too expoitist…
    foramillion.com – never figured out the legalities…it would get weird…videos of stuff people would do for money
    buy domain names for professional athletes before they are professional (just a concept idea, never started)
    gandrvacationrentals.com, built and sold to someone for $1000
    launching adventureinventures to chronicle testing lifestyle design and muse creation for both record keeping and the “lifestyle design niche”…. this turned into thelifedesignproject.com….
    granholm design and development has now kicked back into gear…and i’m tailoring it toward consulting, and social media, and seo management…easier to outsource…new name IT Arsenal
    IT Arsenal days from launching, community building at the lifedesign project…several revenue streams are poised when the research and time can be put in…
    .-= Robert´s last blog ..The LDP | Update: Slowed, Not Stopped =-.

  6. 6 Jonny | thelifething.com said at 12:22 pm on January 10th, 2010:

    A varied carrer my friend. I can’t believe the lemonade stand didn’t set you for life though.
    .-= Jonny | thelifething.com´s last blog ..A Simple Structure That Will Change Your Life =-.

  7. 7 Sean Weisbrot said at 7:31 am on January 30th, 2010:

    I feel kind of sheltered, haha.

    High School
    - Part-time at my dad’s dental office for 4 years (full-time during the summers)
    - Camp counselor one summer

    College
    - Camp counselor one summer

    Post College Life
    - English teacher at several different schools

    Now I’m sick of being a teacher and working on many different ideas such as several import/export ideas, a gentleman’s club (the clean kind, haha), acting (it’s SO easy to get paid to act in China as a foreigner, because if a foreigner likes it, it MUST be good!), proofreading, corporate interviewing for those wishing to get visas for overseas employment, and anything else I can do to earn money where it’s NOT teaching!
    .-= Sean Weisbrot´s last blog ..Johor Bahru =-.

  8. 8 AJ said at 1:36 am on April 7th, 2010:

    We haven’t worked a “real job” in a year and have never felt better – now the challenge is to keep it going….


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