Tell us about crazy/risky things you've done to make your life better.

If its any consolation, that would have melted my heart like a watery cherry sno-cone at a state fair on a hot summer’s day.

I have done plenty of risky things in to make my life better because that is the way throw those ping pong balls into carnival games. I won’t ever know if it worked out though because I can’t see alternate universes. The biggest one was getting in my car by myself and leaving for three months with no destination or plan in mind. Three months and 11,000 miles later I came back home. I got to see all of the eastern U.S. and many people I once knew plus many others. I don’t regret that one but it changed me.

I’m currently unemployed… and trying to get pregnant. I have PCOS, which means I probably won’t ovulate any time soon, but since I only ovulate a couple times a year, I don’t want to lose out on a perfectly good egg. I’m looking for a job, and I know it’s a risk in case I get pregnant before finding a job that they might not want to hire me. But I don’t want to think about it that way.

I’m taking a risk. If I get pregnant, I’m sure the child will be way better than any temporary career setback I might encounter. Plus, if someone doesn’t want to hire me because I’m pregnant, I don’t want to work for them anyway.

When I was 18, I dropped out of college and took a Greyhound bus to NYC. When I arrived I had exactly $17 in my pocket and a change of clothes. I had never worked before and had no skills. Luckily I got a job ($60/week) as an “office boy” my first day, and borrowed $20 from a coworker till payday. I stayed at the Y for about $2.50 a night.

I lived in NYC for 25 years. My last job was a couple orders of magnitude better than my first. The rent on my last apartment was $2500/month.

I dropped out of law school to start a family. Do I have twinges of regret every now and then? Yes, but only for the career I left behind, not the family I gained. Had I waited and become immersed in my career, I’m not sure a family would have ever been in the cards for me.

About 5 years ago I had a pretty high-paying corporate marketing job that I’d been at for 4 years. Hubby and I had a delightful 1-year old son and had just bought our first single-family home at a time when prices were sky-high (however we’d made a killing on selling our townhouse for nearly 4-times what we’d paid for it 6 years prior so things somewhat evened out).

Things started changing at my job, it seemed like a lot of people were leaving with little notice, or rather being asked to “move on”, while a heck of a lot of reorganization was happening on a daily basis. The vibe was pretty scary, and the work environment had gone from hard-working/hard-playing/great communication to very cold with a lot of meetings being held in secrecy. I was traveling a lot and at best seeing my little baby for about an hour a day. This was unacceptable.

After a week of intense soul-searching I realized that my family and I couldn’t live like that any longer, however the thought of sitting at another cubicle at another soul-sucking job where I’d have to play the corporate game and put in 10 hours a day of face time for several months was sickening. I guess I had the “Office Space” moment. With the support of my amazing hubby I left that high-paying corporate job mere months after buying this stupendous house and started my own pet sitting business by myself. I took this terrifying leap in early fall of 2005. For several months I formatted my business plan, figured out how I’d advertise, made a lot of friendly contacts with other local pet sitters, setup my pricing/website, and charted out a territory that would seem feasible. I opened my doors on December 5th, 2005, worked 14-hour days for almost 9 months and by August 2006 hired my first Independent Contractor.

Five years later, I have 6 Independent Contractors working for me, am pulling in nearly 6 figures overall, have been able to volunteer in my son’s kindergarten class on a weekly basis because of my incredibly flexible schedule, and am expecting my second child in January. I’m here in the morning to see my boy off to school and home in the afternoon when he returns. Dinner is on the table for my family at 6:30 and I’m able to maintain our home during the week so our weekends are open to spend it however we please.

Some of the most rewarding moments have been when I’ve been able to help a client in a true emergency situation. Someone’s wife went into labor 6 weeks early one night and we were able to step in and care for their 3 dogs during the 2 weeks they were watching over their baby in NICU. We’ve stepped in when someone has lost a family member on the other side of the world and has to drop everything, or gets stranded in a snowstorm on the way home from work. I’ve comforted people when their precious pets have crossed the Rainbow Bridge, and been there to help them make that difficult decision when their thinking wasn’t clear.

Thinking back, for me this was the equivalent of jumping off a bridge into a body of water and hoping the water was more than a foot deep without testing it first. I was clearly aware that I was putting our family’s comfort and security on the line but at the time there was no other option for me.

About 6 months after I graduated college, I decided that I needed to leave Los Angeles for something new, or I never would. I wasn’t in a lease, had a job that I was able to transfer just about anywhere in the US and although I had a ton of friends, I was not involved romantically with anyone and had no official ties. So I packed two suitcases and moved to Chicago. I had never ever been there, and moved into an apartment that I found online. The job that I was supposed to transfer with fell through and I ended up having a hard time finding a new one. The first year was such a struggle that I often wanted to give up and move back home. But it’s been 9 years now and I love this city so much! I have wonderful friends, and nice paying (albeit somewhat boring) job and a fantastic apartment. I find new things to love about Chicago all the time!

Now, I may have to do the opposite. The love of my life is planning a move to Los Angeles in the fall. I can’t imagine my life without him, but I also can’t imagine leaving everything that I have built for myself these last 9 years. I might come back to this thread in 6 months and post another crazy / risky thing!

I did something very similar to what olivesmarch did. IME, if you spoil your kids, you will not be able to teach them that independence and self-sufficience like olives and I had to learn the hard way. I once had a secretary who lamented to me, “I wish my daughters were more like you.”

I said, “That’s a really nice thing to say to me and thank you. But you wouldn’t treat your daughters with the same degree of abuse and neglect that I went through and those awful experiences are what taught me how to be who I am.”

More on topic: I managed to put together scholarships, work-study, and other money-making gigs to put myself through college. Left my parents’ house at 17 to start school in the summertime, one week after my high school graduation. Six months after I graduated, I packed everything I owned in my car and left for Florida (from Ohio) with no job, only $50 in my pocket, a BP card and a Mastercard. I also was in debt for about $15K in student loans and the car loan. I knew one person, who was the guy that would become my roommate. I became employed three days later, never looked back and never had to go home to mommy.

Four years later, I took a job in SC and did it again: pulled up stakes and moved to a strange city where I knew no one, had no relatives and no friends, and had to use a map to get from my apartment to my job (the first couple days).

Two years later, I did it again: Followed a job back to Florida, to a new city where I knew no one, had no contacts and no support system. 13 years later, I have a very full social life, own my house, and could not be happier.

Moral of the story: Follow your bliss.

Went off to Japan with no plan other than to make money. Instead I lost pretty much everything due mostly to bad luck, and finally made it to Hong Kong with literally no money: no cash, no traveller’s checks, no credit, no bank account - and no return ticket. Crashed on a friend’s floor and lived off about $50 that he loaned me, which I made last two months (ramen for breakfast, lunch and dinner nom nom) until I got a job, and then suddenly had the best time of my entire life. I regret ever leaving.