Trading comfort for the unknown? If anyone can pull this off, you can.

We are only limited by ourselves. At least, that’s what I keep telling myself. We’ll all be cheering you on :)

All I know is that it’s better to take a risk and fall flat on your face, than to live with the regret of What Might Have Been. That doesn’t mean that I always have the courage to do that, but I try because I know it’s the right way to live.

You’re too good to settle, and you already know that! We’re all behind you 100% so jump off that cliff!

11 years ago I was working three jobs, dating an asshole, and generally hating my life. I ended up dumping the guy, quitting the jobs, loading up everything I could fit in my car and moving to California with $600 in my pocket. Insane? Yes. But it was the bravest and most rewarding thing I have every done. I can’t imagine what my life would be now if I had not taken that risk.

That being said….is it funny or sad that I totally nailed that dog/wizard thing?

I just spent the last year of my life in San Francisco for a zookeeping internship. I had been volunteering for years, hoping to get hired as a zookeeper, and it’s the old Catch 22 – you can’t get hired without experience, can’t get experience without being hired. So I finally got accepted into this internship, and it was for a year, which was exactly what most jobs require – a year of experience. I moved away from my *husband*, my cats and my friends to move to a city where I knew no one, for a job where I knew no one, in a zoo I had seen once, for a very small salary (minimum wage), and it was terrifying. But I did it! And now I’m back home with my husband again, looking for local zookeeping work, and I feel very accomplished and much more like I can kick ass than I’ve ever felt before in my life.

And that dog/wizard thing was awesome. I got 11/16!

Speaking very specifically about freelancing, about 6 years ago, I left a very cushy job to start working as a freelancer. For me, it was an unexpected opportunity that came out of the blue and I thought, “Why not give it a try? If it works it will be an amazing opportunity. If it doesn’t work, oh well.” It completely did not work out for me. I realized fairly quickly that I HATE spending my days alone and that although I always worked autonomously, I really needed the office atmosphere to stay on track. This was even more true, once I had a child and desperately needed adult conversation on a regular basis. I ended up getting completely depressed by the situation and ever since I’ve been desperately trying to get back to an office job, but with no luck.
Its not that I would recommend not taking the freelance position, but I think that the issue is less about being a risktaker and more about how much that kind of lifestyle will suit you. Its really hard to be that isolated. It completely suits some people and is the worst thing for others. You have to look beyond all the other issues and figure out which kind of person you are.

I’m married to a freelancer and while it is challenging, and we have to make sacrifices to build his business, I know how much happier he is in control of his own destiny. After living this life I know it’s not for everyone, but for those that love it and work really hard at it, it can be volumes more rewarding than the “9-5”. If it speaks to you, it’s worth stepping into that void sometimes!

You should check out this site: http://www.freelanceswitch.com. They have a ton of amazing information, and a pretty vibrant freelance community (full disclosure: I don’t work for them, but my husband does a weekly comic for them.)

Heh, I’m living the “dream” right now, although it’s turning into a nightmare. Quit my job back in August with the promise of a screen printing studio and a freelancing career in art.

As it is, right now no one wants to hire me and my studio doesn’t have enough money to even get started (we’re just $2000 short and seeing as I have no job, I can’t fund that unless I were making money through screen printing… you get the idea). So for the first time in 8 years I’m unemployed and am living off my loved ones who are supporting me until I either get a job or money magically falls into our lap.

I probably should’ve worked longer and saved up that 6 months of expenses money that I was told to do but if I worked at my job any longer I would’ve shot someone.

At this point in the economy I might be lookin’ at retail positions *shiver*

We’re taking a huge risk with starting my husband’s business – moving to a place we don’t like, where we know no one, all in order to be financially independent enough to move back where we want to live. I’m scared it won’t pay off. I’m scared we won’t pull it off. So the work and heartache and loneliness will just have been for more debt. We’re in the middle of the risk right now so I’ll let you know if it was worth it.

So Linda, just a general comment about your inertia. I think you were in a depression when you were drinking. Of course, I didn’t know you were drinking cuz you were so sly with it. But just knowing you then and knowing you now – you’re a lighter person. Way more positive and optimistic. Part of that has to do with parenthood, yes. But I think a big part has to do with giving up drinking – you gave it up in part to have a family – but alcohol is a depressant that was probably bringing you down. And knowing that you gave it up must give you an emotional high – an inner strength that wasn’t there before. Your writing has been so hopeful and positive the last couple of years. This is corny, but I am proud of you, and you inspire me to be more positive, which is a major reason why I love reading your journal.

What Mama Ritchie said, and yeah, I’d rather regret the things I’ve done, instead of the things I’ve failed to do.
I got 14 right, I do know my dogs from my wizards. I also know lizards from wizards but they don’t have a quiz for that. LOL, and damn you look good in your pictures.

I really love reading about this change you’ve gone through, and it’s inspiring to me.
This weekend I’m taking my very first writing class, which I’m hoping will be the first step in getting my short stories published. It’s scary, because it’s actually saying “I want this…I want to be a writer, and I think I’m good enough to be one”, instead of just having a blog and blathering on about my life. I don’t need to make a living off writing, but I love it, and I think it’ll make me feel like I’m doing something worthwhile with my life. Good luck!!!

No stories, sorry! But I’d have to say… dreams aside… I’m a practical person and in this economy, I’d stick with my day job and write on the side.

My “risk” was minimal, but I am glad I did it. I taught special ed. for years and it sucked the life out of me. Loved my students, but OMG…the politics! The ridiculous laws! The insane paperwork and meetings! Anyway, about 5 years into my career, I knew it wasn’t for me. So, I decided to get my masters degree in Educatonal Technology. 6 years later,(11 years in special ed!!) I took the leap and applied for a technology job. It was a risk in that I wasn’t sure I was legally certified for the job and I knew it would be a HUGE change. On the first day of my new job I remember thinking “What did I do?? I can’t do this!” However, now I know this is what I was meant to do. I LOVE my job. Of course, it has its ups and downs, but overall, I am sooo much happier. I think you should go for it. If it doesn’t work out, you can always do something else. Good luck!

A year ago August we moved from FL, where I grew up and all my friends and family are, to SC, where my husband is from. I had a comfortable well-paying job I loved, but we lived in an expensive area and could never get ahead of our bills. My sister, whom I’m very close to, had just had a baby and it killed me to leave, but we knew there would be better opportunities for my husband here. A year later I still miss my people, but we have never done better financially, are about to own our first home, and our marriage has never been stronger because of virtually no stress levels. It was scary leaving a regular paycheck and I still keep in touch with my old co-workers who were more like a family than anything else, but I don’t regret this move ever. It took two months for me to get a job at the university where I wanted to work, but I did it and I’m so glad we took the risk.
Yours was the first blog I’ve ever read and I thought from the beginning, this woman’s writing talent is amazing – I think you owe it to yourself to take this chance. Life is about having as few regrets as possible I think and it’s always more rewarding when you succeed at something you were scared to do in the first place.

My favourite saying of all time keeps popping in to my head lately, perhaps suggesting I am due for a change. Maybe it will work for you too.

If you always do what you have always done,
You will always be where you have always been.

You decide, I vote Go for it!

I don’t have a story, but just wanted to casually knock you on the shoulder and tell you “YOU CAN DO IT!”

I had to do a spot for a tv station lately that just cemented how much I love (and miss) broadcast journalism. My ultimate goal of becoming an on-air news anchor got me into radio for a number of years, but then I gave up the fight. I left the station that day renewed to pursue that goal. It’s just what I want to do, yanno?

So I don’t have a story. I hope to soon.

This week I signed up for a 12 week certificate cookery course that I have always wanted to do which will mean that I have to quit my well paid job that I have been in 6 years. Hopefully doing that course will lead to me opening my own food related business

My friend finished chemo 2 months ago and they found another tumor last week. I figure you only live once, its bloody scary making a decision that could completely change your life (or even just your career). You only have the one life though, so its better not to regret it.

Nothing particularly untraditional to report in my career, I just want to say – Why in the world did I feel the need to do the Dog v. Wizard quiz? And why did I care what the person who made it up decided was the right answer?

My husband had a unique job that he enjoyed but wasnt very happy with the particular work environment. It was suggested to him by my parents that he should try something else (mostly because his job did not pay well and probably will never be a big money maker) and they financed him starting his own company doing something different. It was a total disaster. He hated it, it did not go well. We took huge risks and lost. We now owe my parents LOTS of money that will take years to pay off. BUT!!!!! My husband realized how much he truly loved his previous job and how incredibly talented he is at it. He was rehired by his old company with much better pay, a promotion and lots of other wonderful things (his absence made them realize his worth). He is happier than ever with his career. Granted we are in debt, but thankfully it is to my patient parents and not a foreclosing bank. It has strained his relationship with them forever unfortunately, but we will have to work through that. Finally knowing what you really want to do in life and finally realizing your amazing talent at it was worth it. Our risk paid off, just not in the way we thought it would. In retrospect there was probably a half-way choice that we didn’t explore, where he could have experimented with the new company but kept the security of the old and not racked up quite so much debt. Ahh hindsight.

Best of luck to you, whatever you decide.

I also have a bit of Teh Complacency. I’m working on it.

I was miserable in my old job. I knew it, but until I got out of it, I didn’t fully comprehend how bad it was, how unhappy I was.
I was ready to get out of Boston, but not sure where to go. I CERTAINLY wasn’t going to quit my job and move some where without having a new job lined up.
Or so I thought. My boyfriend got transferred to DC, and 6 months later I said fuck it, and quit my job in Boston and moved here. I had no idea what I wanted to do, but I networked. I talked to anyone and everyone. It paid off. It took 3 months, but I landed a job at the company I dreamed of working for as a kid. It’s not all sunshine and roses, but if you had told me a year ago that I would be here, doing this, I wouldn’t have believed you. I’m proud of what I did, even if it did scare the bejeebus out of me for those three months that I had to stretch every nickel.

Also, um, 5 days after I met my boyfriend I hopped on a plane to Hawaii to spend 12 days with him there. Talk about risk. My family thought I was out of my gourd, as did all my friends. But here we are, over a year later, and it was still one of the best decisions I ever made.

Regardless, in all cases, just go with your gut. It has never, ever steered me wrong. Listen to that little voice, take a risk.

I have taken risks to change my life; I bought a really trashed “fixer-upper” house all by my self. NO one, not even my mom, thought I could fix this thing up and sell it for a profit (back when the market didn’t suck!). Well, I did. And I made a crapton of money off of it. I also went back to school and took on loans to do it. I followed my dream of getting a degree and found that I will need to go to grad school to become employable. And I will probably do that.

I try to draw inspiration from those things. I know I can take on scary, life-changing things because I have done it! But, the one thing that I feel really scared of is my current job. It is the one thing I feel like I can’t change, at least right now. But it is the one thing that is sucking my very soul out of me; I am so unhappy here that I cry every Sunday evening. I don’t know why I feel I can’t get over this and do something to change. I hope I figure it out soon.

Five years ago I left a relatively cushy job and went to graduate school to pursue a PhD in history. For my husband and I, it meant leaving all our friends and family in Kansas and moving halfway across the country to Florida. It also meant that my paychecks would basically put me well below the poverty line, while my paychecks at my former job contributed fairly significantly to our household income. Thank dog my husband has a good job, or we’d be living out of a cardboard box right now, is what I’m saying. Graduate school has been incredibly hard, incredibly frustrating, and incredibly scary. But it’s also been fabulously rewarding. I’m now writing my dissertation and I’ll have my PhD by summer of next year. I know full well how tight the job market is in history, and that I might not get a job, but I love what I do and I have to believe that something will come through eventually. Following your dreams is scary, yes, but the rewards are endless.

I took the plunge…made the leap…cut the cord…and have been a full-time, self-employed copywriter and editor since January 1, 2006 (my daughter was 18 months at the time).

I spent FOUR YEARS mulling over the decision, but once I made it, I never looked back. Not once.

The clients and projects started flowing in. I found myself more challenged and invigorated than ever. And, of course, the nine hours a day at home alone (hubby at work, kid at daycare) continue to be pure bliss.

Oh, and P.S.? My pay has TRIPLED in three years. It went up about 10% in year one (2006)… had doubled by year two (2007) …and is at a record-breaking pace for year three (2008).

You can SO do it. There is incredible, incredible demand for people who can write coherent sentences and who are pleasant and reliable to work with.

GO FOR IT.

Now, I just need to follow YOUR example and get my fat butt in shape. :-)

In church a couple of months ago they did a whole series on …”If I had 30 days to live, what would I do..” So they asked that we try to live our lives as if this was the case with an effort to unclutter our lives. My hubby has always always wanted to start his own business. He had been given an opportunity to start his own. It was scary, VERY scary…but I just kept thinking, If HE only had 30 days to live, I’d want him to pursue his dream — he was getting pretty disgruntled where he was.

So we closed our eyes and jumped. We had basically 1 month of extra mortgage saved and we set our expectations low. If he can pay the mortgage, I can cover everything else and we’ll be ok (financially). If he can bring that much hom and have a more flexible schedule and be happier, this is a success.

During Labor Day we took off on a weekend roadtrip. He worked weekends before so we could never plan anything like this. I can’t tell you how good for it. He’s been “on his own” for 3 months and his sales have steadily increased (25% a month). He has over 100 customers and has so far been able to cover the mortgage. :o)

Close your eyes and jump. If you only had 30 days to live, you’d want to be doing something that really fulfilled you. You can’t measure success only financially. I can’t even tell you how much happier he is and how good I feel to be able to help him fulfill his dream. :o)

I took a huge risk when I was pregnant with my son and I have never looked back. I was in a PhD program due to inertia…

After college I didn’t really want to get a job and so I stayed in school. It helped that in engineering, you do not pay your own tuition. But as a previous commenter has said, being a graduate student means you live below the poverty level. And the further I got into academia, the more I realized that I did not have the stomach for the bullshit politics of it. (I realize there are politics in every job, but this particular type I could not stand.) So even before I got pregnant I was looking for a way out. The pregnancy was just an excuse, albeit one that made a lot of sense. The day care alone would have cost more than my salary.

Now I work from home 15 hours a week doing editing (not exactly engineering-related, but I do like it and it helps pay the bills) and 5 hours a week teaching childbirth classes (my real passion, but difficult to get enough students to pay the bills on its own). And I also stay home with my now-20-month-old son, and another on the way.

I say listen to your gut feeling. Also, is there any way you could take some vacation from work and give it a “trial run”?

If you only had a year to live, what would you be doing? If it’s anything other than what you are doing now, you need to make a change STAT! I realized that if I only had a year to live, I would not want to spend it separated from my partner who is in the Navy stationed in Hawaii. I’m taking a huge risk, packing up my life and moving to Hawaii with a couple of suitcases at the end of October! Life is short. Don’t waste a minute of it living short of your potential – you have an obligation to the universe to find and live your exponential happiness!

About five years ago, I took a leave of absence from my job to get back into dancing and take a stab at acting and writing.

At first, it was amazing. I felt so freed from the golden handcuffs of corporate life, and so motivated to pursue the artistic dreams I’d always had. I went to an acting conservatory, auditioned for everything under the sun, took daily ballet classes, and did some freelance writing while working on some fiction on the side.

After a while, the romance and excitement were slowly supplanted with angst over money, and I missed the structure of an office and, with the freelancing, I missed the stimulation of being around other people. It was unreal how competitive the New York acting world was, and I found it demeaning after a while to have to audition for projects run by 20-year-old film students who barely knew how to operate a camera. It seemed so unlikely that I would ever be able to make a career out of it, no matter how talented I might be.

Plus, I felt like I had become a leech on my husband — he was ALWAYS supportive of me, but I knew how stressful it was for him to carry us financially, even though I was bringing in some money with the freelance stuff.

In the end, I came back to my attorney job. And it turns out that, for me and for our family, it’s the right thing right now.

BUT…I will *always* be glad I gave it a shot. Because if I hadn’t, I would be left wondering “what if…”

I know that you can pull this off. I’m absolutely inspired by these recent posts – I have also found that parenthood has snapped me out of inertia. Suddenly I realized that now my daughter was going to be watching – what did I want her to see? A happy, fulfilled mommy? or one who is angry with the way she’s wasted her life?

Again, you inspire me. Parenthood = put up or shut up, and you’ve done brilliantly. I think you’ll accomplish whatever you like, Linda.

Wow, it is so amazing to see the transformation you’ve made in your life and writing over the past 5? 6? years you’ve been writing this blog. You’re an inspir-freaking-ation!

Two big risks I’ve taken in the last 2 years:

1) I became a burlesque performer. This was something I’ve wanted to do ever since I saw my first show back in 2003 and I finally got the ovaries to do it in February of last year. It’s been a totally empowering, creative experience and not even a bit scary anymore, and hey, I actually make a few extra bucks now and then :) And awesome of awesome, I will be performing with my troupe at a national festival in San Fran next month. This is normal now, but two years ago it seemed impossibly out of reach due to my own idea of what I could and could *not* do.

2. I became a teacher. Last summer I crazily applied to an alternative certification program and left my stable (if boring) non-profit editing job to become an English teacher for a crowd of over-age, low-skill teenagers in a failing, urban district. I walked in on Day One absolutely terrified and clueless, but I made it through intact, and relatively successful. Today, I am finishing the 4th week of my 2nd year.

You CAN do whatever the hell you put your mind to. And in my case, that current task is keeping my two new lives as separate as possible ;-)

I quite my high-paying-long-hours job in April when I was a couple of months pregnant with this little guy due in November. Now I’m working part time from home, and part time in an office. None of it is a “dream job” but re-evaluating my life and trying to structure it around spending more time with my boy and less time kissing up to agency fucktards is a dream come true.

I worry about money a lot. We can barely afford this. But we’re making it work as much as we can.

I know more than anything that for the next year or so all I want to do is immerse myself in NOMNOMNOMing my boys. After that, the rest of my life is pretty un-planned.

Great post, Linda! For me, this process definitely has an ebb and flow rhythm to it. Eight years ago last June I met my now husband, at a time when I was in the process of trying to jump-start my life by getting out of the small town I was living in (my first big job out of graduate school, great job crappy place to live as a single person). So I meet this guy when I’m about to consider moving across the country. He’s about to be deployed to Bosnia. He’s in the military, which I had always written off military guys as ‘not my type,’ (sounds so underinformed and kind of bratty to me now, but also still kind of true). But we clicked, and had an amazing connection to each other that totally grew over email while he was stationed overseas. I ended up delaying my relocation for a year, he left his deployment with plans to leave the military (which didn’t happen, thanks to 9/11 and a very long stop loss, long story short). We moved together to a new city where neither of us had jobs, got married, dealt with being separated for long periods of time while he was deployed after 9/11. AND I got my dream job. AND we had two amazing kids. AND we lived in a city that I’d always wanted to live in. AND we made some amazing friends. That decision to be more intentional and action-oriented totally propelled my life forward, but not in the way I had initially anticipated, and at times it was really scary. But so worth it.

I hope whatever comes of this ‘wave’ for you feels worth it too!

Sometimes to get the fruit, you gotta go out on a limb.

That being said, here’s an idea. Could you take a leave of abscence from your job, like for 6-12 months? That would give you time to get started on your own and see how it goes. If you end up not liking it, or aren’t making it financially, you could go back to your job.

I admire your faith in yourself. You’ve earned it and it will definitely make others believe in you too.

I have no story to contribute here, other than to say that I see the same crossroads in the distance. The main thing that is stopping me from going into consulting full-time is the fact that I am the primary breadwinner. My husband has not had the most stable of employment histories, and I pay the mortgage, insurance, etc.. We’ve had to delay trying to have another child for a few years while waiting for his employment situation to stabilize. Now that he has a decent job, we’re thinking about all the things we’ve been holding back: Having another baby, buying the Jetta wagon I’ve been lusting over, starting my own gig. It is terrifying.

Based on the economy I’ll probably stay where I am career-wise. I may not be ecstatically happy, but I’m happy enough for right now. The rest will come for us, in time.

I will say this – I read a ton of blogs every day but your blog is one of few I consider a “must read.” I know it sounds cheesy, but you really have a way with words that makes it a pleasure to read. Of all that I read, I think you have the best shot of making it on your own terms.

I just did it.
I left a job that, from the outside, seemed epic. It was challenging, creative, exciting and I got amazing experience….BUT it stopped being what I wanted and who I wanted to be answering to.
I jumped ship about 3 months ago so it’s still new but it’s awesome… I’m freelance, am making way more money.
AND the best part: Sunday evenings, I no longer have that dread in the pit of my stomach.
All I keep saying is: I should have done this a year ago.

In my thirty years in the High Tech industry I have changed my ‘career’ 11 times. Usually that meant taking lower pay, longer hours, and a great deal of uncertainty. Every time I ended up in a better position than my prior one. I wish I had a link to a story by an older lady how said the only things she has regretted in her life was the stuff she didn’t do. Great story.

I went to school for technology and then ended up quitting my job two years into it because I wanted to teach. After going to school at night for two years to get my teaching certificate, I discovered that I HATED it. I guess it’s not for everybody. I ended up finding balancing by working at a school as the technology person and actually really loved that job. Now I’m at home with the kids until they’re in school but I miss working. A lot.

Life is not a dress rehearsal. You’ve only got one chance. Your time is now, go for it. Time flies, especially with kids, so if you don’t make the leap you’ll find yourself five years from now lamenting the same questions. And over the course of that five years wondering about it every day.

I was engaged to be married to a great guy but over the course of our engagement realized, hey wait a minute, do I really want to marry him? Of course this was before Oprah had on her show everyone who called off their weddings! I made the decision 2 months before the wedding to call it off. Scared my pants off but deep down I knew it was right. It was, and I am so thankful that I took that big risk.

I have three young boys and am just a smidge older than you. God bless daycare is all I have to say! I knew that I would never be able to be a full-time mom. I enjoy working, it’s just who I am. I’ve been fortunate to always find a good balance and my husband and I enjoy our “hikes” (for us it’s golf) when we can sneak away but have the boys in either school or daycare.

I took the leap just over a year ago and started my own business. It’s something that I always wanted to do but feared the unknown. I was the one who spent 4 years lamenting it, wondering, imagining it. I finally did it, and so far so good. My only regret, that I didn’t do it sooner!

Yes, there will be adjustments that need to be made. Yes, there will be long nights. Yes, you will need to keep away from the tv and the fridge. But at the end of the day you will be happier, your family will flourish, and the sun will come up tomorrow.

P.S. I’ve been a voyeur on your site for some time now and have finally gotten up the ‘courage’ to start to comment. All I have to say is you make me freaking laugh! I thought I needed some Depends when I read your post ranting on all things Green! Seriously, one of the best pieces of literature I’ve read!! And can you please give some photography lessons…I mean they are brilliant!! Okay, ’nuff said. Take the leap!

I think everyday about going back to school and getting my master’s degree – the practical thing to do would be to get some kind of marketing or journalism or library science degree. I am pretty sure any of those would lead to a good job that I wouldn’t actively hate. But that’s not my DREAM. My dream is to get my MFA in Creative Writing, but that’s just so impractical. I know I would emerge a better writer, but possibly even less employable than I am now.
In the meantime I decided I needed to start doing all the things that scare me, that I tell myself I just can’t do, so I am going to write a book. Probably a bad, unpublishable book, but a book nevertheless.
For the record, if someone who is as motivated, funny, and a great a writer as yourself can’t make it work career wise, there is no hope for the rest of us. I am rooting for you.

I don’t often leave comments because I’m a born lurker, but I have to thank you for that last little paragraph. After sitting in the parking lot this morning blubbering over my frustrating job, that’s what I needed to be reminded of: quit with the blubbering and make my own changes.

So good luck! And thanks for the inspiration.

I’ve been reading (and loving) your site for a while now, but this is the first time I’ve commented. Good for you for pushing yourself to strive for MORE in your life.

Here’s my story: A few years ago, I was in grad school, 3 years into a PhD program in English Lit. On one level, I was really successful in my program — 4.0 GPA, great advisor, great teaching assistant assignments. Except I was completely miserable — I hated the publish or perish pressure of grad school, hated that my program emphasized focusing on my own research over spending time on my teaching so that my students could, you know, actually WRITE when they came out my classes, etc.

During grad school, I’d also been working in the summers for a wonderful company, teaching kids’ reading classes. It was the most fulfilling work I’d ever done, and I wanted to work for them full-time. Unfortunately, the best answer they could give me was that they thought they’d maybe have a full-time job available in the late fall and I could apply for it if it did turn out to come available. Not exactly reassuring when you’re thinking about taking a huge leap.

I finally decided, though, that leaving grad school and striving toward something better was what I needed to do for myself, even if the job I wanted didn’t work out. So, I took the leap. It was incredibly difficult, and I was out of work, flat broke, and freaked out for a month. But eventually the job I wanted DID come through. I’ve gotten several promotions since then and now I’ve got pretty much my dream job as a curriculum developer and writer for that same company.

Wanting to get out what I put in is one of the reasons I chose to start my own law practice rather than accept offers from the firms. That and the fact that I’m a single mother (single in the sense of its just been me and him ever since, so really single) so I needed to have flexibility.

Two years into it and I am definitely grateful for my independence. Today I’m leaving my office early to take him to his first day at a new cricket clinic. Couldn’t do that at a firm.

But I lack discipline and here I am blogging when I have shitloads of work to do. So sometimes I wonder if this procrastination issue is going to defeat me.

I have a knot in my stomach some months, like this one when school fees are due, and I just returned from holiday, and office rent has increased, and I wish I had a paycheck I could depend on – BUT it always works out!

Health insurance is a killer though The benefits in a company are great from that perspective.

I think you should go for it if you can.

I wanted to recommend Dawn’s “This Woman’s Work”. You can read her risks and rewards in finding the working life she wants, freelancing and being with her family. I think she’s realistic in describing both the risks and rewards.

http://www.thiswomanswork.com/

I don’t have a freelancing story, but I did change careers. I was an attorney for quite awhile and decided I wanted to do tax accounting. So, I went back to school at night, took the CPA exam, and got what I thought would be my dream job. But then the office I worked for went through a big change and the kind of work I signed on for dried up and I ended up doing completely different work I didn’t enjoy and working crazy hours. Ultimately, I went back to the job I had before. I’ve been here three years since then and frankly I’m still a little bored and dead-ended, but until I figure out what other thing I might want to do with my life I’m staying here.

The thing is, even though it didn’t work out, I am really glad I tried tax accounting because if I hadn’t I’d have spent my life wondering if I’d missed something I would really have enjoyed doing. It was better to try it and have it not work out than it would have been not to try it at all.

7 years ago I was working in retail..so not what I went to college for…I HATED it. I hated the hours. I hated the holidays. I hated people. It out and out sucked. Then the wife of my husband’s boss was working for a company that was expanding rapidly…they needed bodies..trainable people to fill positions. I interviewed and was hired a short time later. Took a substantial pay cut to just get “out of retail”. I worked hard and within 6 months had been promoted and was making more money than I was in retail. Seven years later I am still with that company. I enjoy my job and am about to be promoted. I am lucky enough that I work remotely three days a week and in a traditional office setting the other two. While I am more productive at home, I find I need the adult interaction the office provides…otherwise..for me, I’d go a bit crazy. Anyway, it was a big scary step 7 years ago. I walked away from a very easy job that I hated into one that I was totally not qualified for..as in ZERO training. I was lucky I had a wonderful boss who truly believed that anyone is trainabl! My next big move is to actually take the big exam to become licensed. It scared the bejezus out of me because the pass rate is like 8%. But I know I will be in that 8%!

I have a success story that involved stepping out of my comfort zone.

I was working for company1 and had good pay and terrific benefits, but I was miserable. I hated the job so much.

Then I heard of a job at company2. It was a new position they were just creating and the person who got the job would be able to design everything about the job themselves. It was well within my area of expertise at the time so I applied for it and got the job! The one problem, the pay was less. Kind of a big step down pay wise even after negotiating a lot.

Anyway, I decided to make the jump, take the chance. Not only was it by far the best job I’ve ever had, but I got promoted, got raises and within a little over a year I was making more than at my old job.

It was scary, but SO WORTH IT!

You already know the stories behind my several leaps of faith over the last few years… Each and every one of them has yielded a richly rewarding learning experience. That’s not to say I have actually *become* rich from any of them, but I have certainly learned a lot about myself and the strength of my mariage and friendships and I wouldn’t trade that for anything. Sure, it hasn’t always been fun and we’ve had to make a lot of sacrifices, but it was all so incredibly worth it.

So I say go for it. You’ve already been building your business for years and you are extremely talented. You’ve proved that you have the drive to mold your body, your house and your family into what you want it to be, so why not tackle your career next? You can do it!

I’ve taken two big risks in my life. The first was moving to a city 1200 miles away from my friends and family with a man (now my husband) I had been (rockily)dating for three months. To a city where we had never been and had no jobs or apartment waiting for us. The second was quitting my day job three years ago that had room for growth, had status, was pretty cool, and had benefits, in order to make art full time. Both of these things did/are working out. They easily couldn’t have. Whenever I get freaked about making big decisions, I think about the mission to Mars. When/if we ever go to Mars it will take about 6 months to get there. The earth will be a tiny speck, almost invisible. If something breaks or if someone gets very sick, there will be no immediate help. Once the astronauts leave Earth’s atmosphere, there is no turning back. There aren’t that many decisions in life of that magnitude. Having kids is sort of one, deciding to move or quit a job is not. If the money doesn’t work out, you can find another job. If you get lonely at home you can meet a friend for lunch, go work from a cafe, or make sure you have meetings in an office once a week. I can’t think of a better example for your kids than living your dreams. Do it. It ain’t no Mars mission!

So many great stories here, and I am not sure I have much more to offer.

Still, without providing tedious details, let’s say that, in fact, I have taken many risks, despite my own inertia and complacency. I’ve taken some big risks & radical steps. Some of these have paid off. Some have not. Some I regret. Some I do not. In pushing myself out of my comfort zone, I thought, “nothing ventured, nothing gained” and all that; however, I think on occasion I have taken the risk more because I didn’t want to be someone who walked away from a challenge than because it really was the right choice for me.

I have yet to figure out when it’s “worth it” or “right” to take a big gamble & a leap into the unknown. I am contemplating another big gamble & wish I had figured it out by now!

I think this choice you face has little (if anything) to do with your talent or ability, because I think we all here testify to the power and beauty of your writing. I agree with the person above who wrote that you should try to figure out what KIND of person you are in terms of needing the structure of the office, the company of professional adult coworkers, etc. This matters more than your talent (which none of us doubt) & your proven record of success at achieving what you put your mind to accomplishing. Will the risks be worth the reward? Can you live with the worst that could happen? Can you live without the best that could happen?

Good luck!

I was where you are three years ago. Today, I’m in my third year as a marketing communications consultant. It’s often lonely, and chasing work like a golden retriever bites the big one. But it’s also been wonderful for my family. I don’t have many regrets about leaving more traditional (and often more lucrative) corporate work. My personal pep talk consists of two statements. 1. People with far less talent and motivation than you are out there making this work. 2. And if it doesn’t work, you can always go back.

Go for it.

I don’t have any stories of risk-taking, but I am on the cusp. I have been in a holding pattern since graduation college and boy is it frustrating. Hearing your confidence and plans and overall level of pep has started the “hey, I can do that too” sorts of thoughts. Thanks!
And thanks for the incredible dogorwizard quiz. A few were definitely NOT wizards, those charlatans.