Quitting my job to chase dreams: sanity or madness?
April 18, 2010 3:06 PM   Subscribe

DreamFilter: Quitting my job to travel, write and then become self-employed. Madness or do-able?

I've worked for a big company for almost six years in the online advertising space, rising from entry level to the bottom rung of middle management. My most recent promotion was in November of last year, so I've been in my current role for about six months.

While I don't hate it, my dream is to make my living as a writer of fiction. However, I know how unlikely that is, and as I also very much like training people and public speaking, I am wondering if there is a way I can keep a roof over my head through training, free myself from the nine-to-six grind, and have more time to write.

I've also had a life-long and mostly unfulfilled desire to travel for a period. So I have been thinking of a plan something like this:

(1) Leave my job early next year
(2) Travel for six months
(3) Come back to the city where I live now, and work on getting set up as an online advertising consultant/trainer
(4) Write more
(5) Profit!!

Well, maybe not so much profit.

I've done some preparation/investigation - I've set up a basic website to advertise online consultancy services and assess whether there is much interest in the space (there is some), I've written a short-ish book for children and am working on a pitch to an agent through a friend. I have a rough idea on how much money I would need to make as a consultant, but no business plan as yet.

Financially, I have the means right now to support myself for a year or so with no additional income, and I don't have kids or a mortgage. My girlfriend is understanding and encouraging. I'm 30 right now, would be 31 when I was starting this.

But while all this makes sense to me, I can't shake the feeling I am a bit old to be acting so 'irresponsibly'. The money I have is a one-shot deal from share options, and part of me says I should really be spending it on the deposit for a house rather than a jaunt around the world. And I shouldn't leave my job when (a) I am doing well and (b) the job market is terrible.

My questions are, then, am I following my dreams in a responsible manner, or am I being completely reckless? If I am to do it, are there other things I should do in advance? If you were interviewing me in 18 months, what would you think of someone who effectively took a gap year in their 30s?

Any advice/insight/tales from your experience much appreciated.
posted by StephenF to Work & Money (17 answers total) 11 users marked this as a favorite
Maybe a compromise: save the jaunt around the world for after you've successfully gotten your new business venture going. That way you can keep most of your savings hanging around, and if you start making money, you can still put it down on a house.

One of the main reasons to work for yourself is so that you can potentially take extended vacations at opportune moments, at least in my mind. Maybe your big trip can wait a little while?

To be even MORE responsible, you could wait to quit your job until you're actually pulling in some money from your writing, etc.

But international travel sure does sound awesome too. :)
posted by nosila at 3:15 PM on April 18, 2010

I think this is a noble goal. Having said that: many successful authors of fiction were perfectly able to do their writing in their off-work time, mornings and evenings and weekends and so forth. They were even able to take extended vacations and travel the world and see amazing things, all while holding down a job. I guess it all depends on your talent and your drive, and your contacts. I personally would not attempt this until I was rock-solidly established as either an advertising guru or an author, but that does not mean others shouldn't. Best of luck to you either way!
posted by turgid dahlia at 3:16 PM on April 18, 2010

I did it at 39 so that should be the least of your worries.

My only suggestion would be switching the order of your goals, for pragmatic reasons. Set up the business/site/blog/feelers to potential clients etc for 6 months/rest of 2010 and then start the travel - you can always check stuff over email/internet and slow down/plan your projects accordingly i.e. tell clients you are "on a big one" during your travel so as to keep them in the loop for when you return.

(on preview, what nosila said)

Alternately, see if you can find some reason to write/document/photograph or whatever during your travel that might a) help with you pr b) get you some money and/or c) offer it to some community site or blog for the increased visibility

you can write anywhere (at least I would, on a balconey in Bellagio overlooking Lake Como rather than my kitchen ) ;p
posted by infini at 3:34 PM on April 18, 2010

I don’t know if this will help you, OP, but I did (and hope) to do similar things to your stated goals. My goal was a freelance business and also to eventually be able to travel internationally on a more frequent basis. I left my job a little ove a yea ago.

Some things that I learned along the way, although remember we are in different type of businesses, etc., so take whatever applies to you. It may be harder than you think in the first few months. Will clients fly into your lap? (Enough to meet your monthly goals?) Have you thought about marketing? How will you get your clients to pay you ontime, etc.? When I did my crazy plan, 1) I had enough saved for a few months (not as much as you, smart thing to do!) 2)) landed one client who promised a lot of work. I did get immediate work, but that same client didn’t pay for 5 months, and I was paid right before the bank account completely emptied. I’m better at having conversations with clients and even putting these things in contracts, now. I also made close to what I made at my fulltime job over the course of the first year, but the hours were unpredictable although it was at fewer of the number of hours that I worked before. I’m just suggesting that there is a learning curve in the beginning. After going through that I put more money in the bank – work has slowed this year but I am much calmer and don’t make stupid choices with a much greater buffer in savings.

If you were a friend of mine and from my experience of starting a business (and knowing people who have done the same), I would suggest that you shorten the travel plans – perhaps a month. Then launch your business. You can do the travel later. You never know, you may beat the odds, though.

One more thing. Lots of people told me to first work for clients for several months and then quit my job . For me, just quitting my job first was better. I knew that I had to make it work. It was hard enough for me to gather the courage to quit the job, but by doing that action I only had one direction to go (make this work or else).

Re: being “too old” Are you kidding? Lots of people told me I was a nut, but they hate their daily lives and their jobs. Try. Create it. Even if you sink, you gave it a shot and you can try again. If you have experience in the field and that much in savings you are in a really good position to make this work. I am even older than you are - I don't think age makes a difference at all. You are never too old to dream, try new things, learn, and create.

Feel free to memail me if you want encouragement to jump or want to commiserate when you do this. But I feel freer now than I ever did at any of my jobs. Jump.

posted by Wolfster at 3:48 PM on April 18, 2010 [1 favorite]

You could join us Vandwellers; use some of your funds to buy a camper van or a cheap RV, a camp stove, grab your laptop, and hit the road; travel, write, repeat. You'll spend a lot less than you would paying for hotels and transport, you'll have an unforgettable adventure, and you can see how you like the dream-chasey lifestyle. Admittedly you can't drive over the ocean, but you can save that for after your first bestseller :)
posted by The otter lady at 3:49 PM on April 18, 2010

One more thing. Lots of people told me to first work for clients for several months and then quit my job . For me, just quitting my job first was better. I knew that I had to make it work. It was hard enough for me to gather the courage to quit the job, but by doing that action I only had one direction to go (make this work or else).

This was true for me as well. I wanted to think and ponder, then blather and write. Working a fulltime job just wasn't doing it for me. It was the quitting that gave me the headspace to contemplate the future and all the possibilities therein.

Take wolfster up on her offer - mentors and networks are the backbone of a freelancer's life/career
posted by infini at 3:57 PM on April 18, 2010

Best answer: Go, do it! I know several people who have done this and never looked back. I'm not sure about the idea of setting the business up first - I think it depends on the type of business. Do you need a lot of in-person contact with your clients? If so, then travel first. If not, then you can do business from anywhere with Skype, email, etc.

Also, what about your girlfriend? How serious are you... would she travel with you, does she have another job, is this her dream too? Just wondering, because if you are doing this together, as a couple, that gives you even more of a cushion should things go wrong.

Think about where you would like to travel to and how you like to travel. There's a big difference between rural/urban environments, adventure travel, luxury travel, etc. Budget carefully, and it might be cheaper to travel than to live at home!
posted by metametababe at 4:33 PM on April 18, 2010

I don't have any advice for you, but I'm close to your age and I'm quitting my job to travel for several months. This is our chance, dude. Do it and don't look back!
posted by HotPatatta at 4:36 PM on April 18, 2010 [2 favorites]

You only live once, right? But if I were you I would try to write after work, finish up a novel or something and shop it around before you quit your job to write.
posted by delmoi at 6:15 PM on April 18, 2010 [1 favorite]

If you were interviewing me in 18 months, what would you think of someone who effectively took a gap year in their 30s?

I got my old job back after I quit to travel for a year. I wasn't worried about it when I left and it wasn't certain by any means. My life needed what I got from traveling terribly bad and that was my focus at the time.

As it turns out I'm going nuts back in the cube job after what I experienced traveling, so I'm looking into finding something that works for me the same way you are.
posted by MillMan at 6:20 PM on April 18, 2010

You might want to check out this advice from Metafilter's own jscalzi. Be sure to check out point #2.
posted by tdismukes at 7:15 PM on April 18, 2010 [3 favorites]

You might want to check out this advice from Metafilter's own jscalzi. Be sure to check out point #2.

That's some really good stuff, thanks for posting it.
posted by the foreground at 8:02 PM on April 18, 2010

Best answer: I did something similar to this, and can say with 100% certainty:

-Travel. Now. A lot. You have no kids and no mortgage; a new small business is like an infant that must be cared for 24/7. The suggestions to leave after you'd started the business made little sense to me. The older you get, the more responsibilities and anchors you'll collect, and this will be the one thing you'll wish you'd done more of.

-Do you write regularly now, or is it something you'd do if you had more time? Everybody wants more time. Full-time writers want more time to write. Rather than wait for the perfect 6-hour chunk of time in a quiet house in the woods/on the beach, I find it helps to get into the habit of sneaking in as much writing as you can right now, whatever your circumstances. Julia Cameron has a lot to say about this. Not trying to get you discouraged, I'm just saying that if you wait for a specific time/place/set-up to get down 'n dirty with your writing, you open yourself up to subconsciously putting a lot of pressure on yourself when the time does come.

-Have you considered asking for a leave of absence from your job? I know a few people who managed to secure several months to a year's worth of free time this way.

-I would absolutely start getting the ball rolling with your post-travel work plans before you go. Post-travel stasis, nostalgia, and general disdain for the "regular," stationary world are common. If you don't have a clear plan about what you are going to do when you get home, and perhaps people who are expecting things from you by a certain date it can be far too easy to take your sweet time readjusting to the real world. I'd like to think that this is easily avoidable with a little planning.

-Alleviate financial 'am I being a dumbass?' anxiety by traveling on the cheap.

-Alleviate professional 'am I being a dumbass?' anxiety by seeing if there are any contacts you could make, meetings you could set up, things you could investigate about your potential book or business? Places you could stay in for a few weeks to volunteer your expertise? That would also give you something to put on your résumé.

-jscalzi's financial advice is great. However, when you're talking about the beginning of any writer's career, you're usually talking about a period of not having a lot of money. If you want to devote less time to $-work and more time to passion-work, one of the best things you can do isn't just find a job that pays you more per hour, but spend less. I know a lot of people who never 'follow their dream' because they'd rather have TiVo, shoes, and Starbucks. If you are mildly middle-class, you already have it pretty good compared to 90% of the rest of the world, and can cut back on a few things.
posted by blazingunicorn at 10:56 PM on April 18, 2010

Do it.

If you don't, you will always question yourself "What if..?" You can always find something else afterwards if it doesn't go well.
posted by SRMorris at 1:50 AM on April 19, 2010 [1 favorite]

I don't have any advice for you, but I'm close to your age and I'm quitting my job to travel for several months. This is our chance, dude. Do it and don't look back!

Me too! Follow your dreams. man!

Practical advice: what can you do now to minimize the pain of such a dramatic loss of income? I know you have enough money for a year, but the more you have in the bank the better in my opinion. It's hard to follow your dreams when you are stressed about finances, and the extra money you cut back on this year may be enough to finance a good chunk of your travelling.

Do you have cable? Cut it NOW, and look at your potential $100+ in savings each month. Put the money in a travel account. Internet? Can you hook into some local free internet? This might not be as reliable or strong, but again, $50+ per month. Expensive habits like going to bars or smoking? Cut back! Be creative! Rent a room! Walk some dogs!

You are fortunate in that this isn't some fly-by-night crazy plan that you're doing tomorrow. You're planning on leaving early next year. Things to consider: where are you going to travel? What is your bare minimum standard of living? What can you afford? How comfortable are you sharing rooms with strangers?

Travelling somewhere like Canada, for example, will be cheaper in the short run in terms of getting there, but more expensive in terms of food and lodging. SE Asia, on the other hand, will cost quite a bit to fly to but you can bum around for much longer for the same amount of money. Will your girlfriend be travelling with you? Do you need to solicit her input on where you will travel?

Forgive the assumption that you are living in the United States, but it will be January when you leave next year. Are you okay with the cold? Sightseeing and travel, to me, loses its fun value by about 100% when it's cold outside. If this is true for you, you may want to consider a warmer locale.
posted by amicamentis at 9:01 AM on April 19, 2010

DO IT. 30? Pshaw. It's the new 25.

With that said, you sound like you're trying to do a lot - my only concern would be if you're biting off more than you can chew. Think ahead, but be willing to change your plans. There must be ways to incorporate your writing into your travel.
posted by chrisinseoul at 9:57 AM on April 20, 2010

Create a back up plan so that you are not disillusioned later. Keep in touch with former colleagues and friends. Stay afloat.

Also, why dont you write part time if that is possible?
posted by bostonman at 9:07 PM on June 9, 2010

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