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You joyfully take the job with the prestigious firm, only to lament the back-stabbing culture.
Or you accept a cubicle instead of following the call of the great outdoors.
You swear it’s only temporary.
But then one year stretches into another. You build a great looking resume instead of a life you love.
Place and atmosphere are vital to our well being, yet many of us consistently undervalue it. It’s not just what you’re doing that matters, but where, with whom, and how.
How many of us would accept a job to work on an isolated island, surrounded by hostile natives, just for bragging rights? Unfortunately, many careers don’t offer much better.
Having just returned from flat hunting in London, I was struck by the idea that searching for “home sweet home” is nearly the same as looking for “work sweet work.”
(The fact we never say the latter only emphasizes how often we fail to take these concepts to heart.)
Neither process has to be hard. If you have the skills to find a place to live, you can find a career that fits. You just have to have a plan.
5 tips to shape your career landscape
Here’s how we managed to search one of the world’s largest cities to find a new home in under a week. Turns out, the same strategy works when looking for a comfortable career.
1. Ignore well intentioned advice
My husband’s new office will be in the far, northwestern area of Greater London known as Ruislip. Most of the people who work there choose to live in nearby suburbs, or farther out in trendy areas like Beaconsfield or Gerrards Cross.
They love it.
But we knew right away those places wouldn’t be a good fit for us. For example, we wanted a place that didn’t require a car for at least the first year. We valued proximity to the city over square footage.
Neither set of criteria is right or wrong. It’s just personal.
What was strange was how resistant others were to our ideas. When we talked to people who lived in Ruislip or in nearby areas, they honestly thought we had a screw loose for looking anywhere else.
The more we talked with them however, the more we worried they might be right. It was undermining what we thought we wanted for ourselves.
My point is, even very well intentioned people (or perhaps especially well intentioned people) often have difficulty giving any advice other than what they have chosen for themselves. They might acknowledge that everyone has different needs, but unconsciously, they want to justify their own decisions.
We say people are different, but we advise as if everyone is identical.
Do you see the connection to choosing a career? People do the exact same thing. You don’t realize how powerful group think is until you escape it.
It’s okay to have someone challenge your ideas. In fact, I think that’s healthy.
But to find the environment that’s right for you, you may have to ignore or leave some well intentioned people behind.
2. Ask for adjectives
In a guidebook on London for Londoners, they describe the neighborhood of Hampstead as “bookish and arty.”
Touring through Hampstead myself, I might have said it’s hip, without being edgy. My husband noted it felt vibrant, but not frenzied.
I don’t know that I could have come up with those adjectives as my criteria had you asked me. But as soon as I heard them and saw the place for myself, I thought, “this is it.”
Before you consider working at a company, ask them for the adjectives they think best describe the culture and working environment.
For example, descriptions like “prestigious” can be followed by words like “intense” or “competitive” if you dig a little deeper.
Is that right for you? Only you can decide.
3. Know your people
While there, we attended a party thrown by friend and fellow blogger Arvind Devalia. At the time he made his guest list, he had no idea what neighborhood we’d likely be living. He just invited some Londoners he thought we’d enjoy meeting.
Imagine our surprise to discover more than half of them lived in Hampstead, the very neighborhood we’d chosen!
Sometimes you find your people, sometimes they find you.
Every place I’ve ever worked has described themselves as a “family,” but it took more than 10 years in the workplace before I experienced the feeling myself.
That’s not to say everything was heaven. Coming from a rather dysfunctional family, I wasn’t even sure having a “family” at work was such a good thing.
It certainly didn’t prevent me from calling some policies dumb, or occasionally bickering with co-workers on approach or protecting our imagined turfs.
What I will say is that every frustration was offset by an incredible generosity and camaraderie I didn’t believe existed until I experienced it. I sometimes disagreed with my boss or co-workers, but we always had each others’ back.
I’ve never felt more loyal to an organization and its purpose in my life.
It’s hard to know whether you’re going to inherit a family when you take a new job, but try to spend as much time as you can with them socially before taking the plunge.
They always say that people leave bad bosses, not bad jobs, but that’s only half the truth. An enemy in accounting who holds up your work can be just as frustrating and emotionally draining. Think bigger than the person above you.
4. Be honest with yourself
Once we narrowed down our neighborhood, we were struggling to decide between two flats. One had an amazing, private garden (what Americans refer to as a backyard), but was more expensive. The other looked out onto someone else’s lovely garden.
If we’d felt the garden was important, we’d have paid the extra money. But we realized that we had a perfectly good backyard now that we hardly ever used.
What we really wanted was a nice view.
As I’ve said many times, knowing what you want and why is not straightforward at all. It’s worth spending some time (and ego) debating your own preconceptions.
For example, you might think you couldn’t handle a commute longer than 15 minutes. But what if you could do the commute on public transportation and use it to read, something you miss in your life right now? Maybe what you hate is the frustration and waste of time that comes with driving, not commuting per se.
5. Beware the zone of indifference
Those lucky enough to choose between two great positions often don’t feel lucky at all. Instead, they agonize over the decision in an attempt to optimize.
We did the same thing, trying to decide between the flats we loved (even after the big garden a-ha).
One had a bigger reception room (a dining/living room combo), but the other had more storage. One decreased my husband’s commute, the other was closer to a large park for our daughter.
On and on, back and forth.
Gary Klein, the father of naturalistic decision making, calls this the “zone of indifference.”
The idea is this: if one choice is obviously good and the other is obviously bad, it’s easy. Go with the one that’s obviously good.
When the choices are very close together, our first instinct says that this is going to be a very difficult decision indeed. We’re probably going to have to study the problem very hard, do some research, make lists of pros and cons, etc.
In fact, it really doesn’t matter which choice you make–they are essentially equal. Which means you can stop agonizing and just pick one.
Counter-intuitively, the more you contemplate your choice, the more regret you’ll feel over the option you decided against.
A work environment checklist
Finding the right environment can get complicated by competing desires. For example, most people will say they want a “challenging” environment, but few sign up for a “stressful” one. And while “adopting a persona” may sound negative to your ears, it’s essential to careers like sales, teaching, therapy, and (obviously) acting.
This checklist isn’t meant to be exhaustive as much as it’s intended to help you unravel some of your career conundrums.
In general, environmental considerations can be divided into three categories: physical, emotional, and social. The questions below are meant to be answered with your ideal working environment in mind.
Physical (what does your job look like?)
- Inside or outside?
- City or rural setting?
- How long does it take to commute?
- How do you get to work (car, public transportation, walk etc)?
- How often do you travel?
- How many hours do you work?
- Cubicle, office, or shared space (i.e. lab, kitchen, or classroom)?
- Noisy or quiet?
Emotional (how does your job make you feel)?
- What’s the pace of your work?
- Content or driven?
- Playful or focused?
- Relaxing or stimulating?
- Stable or enterprising?
- Predictable or unpredictable?
- Structured or unstructured?
- Can you be yourself or do you adopt a persona?
Social (with whom and how do you interact?)
- Do you spend most of your time with clients or colleagues?
- Do you lead or follow?
- Do you work in teams or on your own?
- Collaborative or competitive?
- Flat or hierarchical?
- Large or small organization?
- Liberal or conservative?
- What are the demographics of your colleagues?
Not all of those factors will be important or even applicable to your situation. The key is to identify the handful that are and commit to them.
There’s this vague notion that you have to sacrifice if you want to be successful, and sadly, the quality of the workplace environment is often the first to go.
We think we can drain our emotional bank accounts to fill our physical ones without penalty.
Now you know better.
The question is: when are you going to do something about it?
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50 Responses to Finding A Career That Fits
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- May 31, 2011 at 9:32 am
- barbara
- Said...
An isolated island with hostile natives… give me a moment I’m having a flashback. OMG!
I love the way your mind works. Comparing house hunting to job hunting is spot on. I’ve moved many times in my life, and I’ve had many diverse careers, but I never thought about the correlation to house hunting.
As for decision making… I sometimes jump too quickly and then may regret the choice but I accept it’s my impatience and try not to beat myself up over it.
A former friend of ours is the type of person who agonizes over every decision from white or brown rice to mac vs. pc. She agonized over the last one so long she missed the opportunity for a new computer that still had windows xp and ended up with vista.
She does this with almost everything and it’s painful to watch. I’m all about researching products but at some point you need to pull the trigger and just do it.
Of course she does enjoy beating herself up over her ‘stupid’ choices so I guess she gets satisfaction in that. Which is why she’s a ‘former’ friend.
I’m very excited for you and your family’s big adventure of moving to England. So happy we have the blogosphere to stay in touch.
I would have chosen the same area you did. Sounds very much like where I live.
Great post! Thanks.
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- May 31, 2011 at 9:55 am
- Chapin
- Said...
This is a great post! I am going through both an apartment and job search at the same time (moving out of the area) and I have been getting many opinions. People feel very strongly about where their friend or loved one chooses to live! I am getting so many mixed opinions but I am lucky to have an instinct toward one that I will likely follow. I love your adjective idea as well – I definitely will use that in upcoming interviews. Great post!
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- May 31, 2011 at 10:04 am
- Lindsay
- Said...
“We think we can drain our emotional bank accounts to fill our physical ones without penalty”.
I’m suffering through this right now. I’m draining my emotional account to fill my physical one. It’s not worth it. I have reached the point where I’d rather be poor than miserable. My Mom always says “money isn’t everything!” and she’s absolutely right.
Wonderful analogy, good work on this article!
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- May 31, 2011 at 11:01 am
- Brandon Yanofsky
- Said...
Your point about being honest with yourself is soooo important. Not only in careers but in life as well.
There have been so many times where I tried to trick myself. I remember wanting to volunteer at two non profits, take a full level of classes, do a sport, and a job. It was well intentioned, but deep inside I knew it was too much. But I didn’t listen and got super stressed. And I ended up having to drop most of it.
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- May 31, 2011 at 11:11 am
- Martha
- Said...
I think it is very important to know the difference between ‘wanting to do things’ and ‘wanting to want to do things’. When I ask myself if I really want to do it – or if I’m just dreaming that it’s something I want to do, the choices become clearer and I don’t tend to overcommit.
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- May 31, 2011 at 11:19 am
- Denise K. Rago
- Said...
This is one of the most incredibly helpful posts I have ever read…anywhere! Thank you. I want to print it out and wallpaper my writing/working area with it.
“We think we can drain our emotional bank accounts to fill our physical ones without penalty.” One of the best quotes I have ever heard too. So much food for thought here. Thank you so much!
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- May 31, 2011 at 1:19 pm
- Shanna Mann
- Said...
I thought the point about not worrying over two essentially same choices was a good one. I never thought of it that way, but the next time I catch myself obsessing over minute differences, I’m totally going to use that.
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- May 31, 2011 at 2:04 pm
- Marc Sokol
- Said...
I think of it this way: you and your family are going to have great experience. The question is what do you want to make primary amongst that set of experiences?
Years back I faced a similar choice, briefly looking at a house in Pinner (not far from Ruislip, in what appeared to be a quaint little English village), but instead chose a flat in Maida Vale for its easy access to the heart of London by tube, bus, taxi and on foot. We loved the vibrancy of the city and all it could offer, and I expect you will have much of that at your doorstep from Hampstead, plus access to the Heath. By the way, I expect you will need car in Hampstead, just so you can be more spontaneous and efficient in your discovery of all there is to offer. But you can rent one as needed during your first year.
I don’t believe you were caught in the zone of indifference as much as you were facing the limits of critical thinking where you have limited access to the criteria that impact your decision making….critical thinking is not just separating good choices from bad ones; it is also the ability to distinguish amongst several good choices. House hunting, far from home, with a limited time to do it, and knowing that you don’t have access to all the information you need, makes the task all the more challenging and often triggers the emotional side of what you hope might be a straightforward logical task.
You stumbled onto a great resource — meeting others and asking about what makes their experience special (in this case in Hampstead vs being even further outside the city).
When checking out a potential employer, it’s good to speak to current and former employees as well as check out sites like glassdoor.com. Similar advice applies here – follow up with an expat who lives in London – even better find one who lives in a small town further out and then one who lives in your target area. See what they each say as the pros and cons. That will quickly help you expand your sense of what may be possible in the new situation. You should be able to find links to blogs about life in London and surely the experience of Hampstead.
For what it’s worth, we never regretted the choice to move closer to the city. My advice is to be clear, even write down, why you chose the option you pursued, so you can revisit that and learn from it should you find yourself someday romanticizing the option not followed.
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- May 31, 2011 at 3:43 pm
- Cara Stein
- Said...
Love this! On all of my job searches, the only objective I ever had was to get a job. With experience, I learned that I cared about commute time and whether I would have to dress up, but I still didn’t look any deeper than that. It was never a matter of whether I would choose them, it was always just hoping someone would choose me. You really leave a lot to fate/luck that way.
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- May 31, 2011 at 4:39 pm
- Cherry Woodburn
- Said...
Excellent post – well written as usual and a thought provoking comparison between home and job hunting. Like many of the commenters I will use some of the lessons from this post.
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- June 1, 2011 at 12:11 pm
- Melissa
- Said...
I really enjoyed this post. I’m currently a stay at home mom and even though I am not looking for work, I find your writing thought provoking and inspirational, and not limited to the workplace. I really enjoyed this post. Sometimes, I find myself paralyzed by indecision and making that list of pros and cons. It doesn’t help. It makes the anxiety of the decision that much worse. I also know many well intentioned know it alls (and can be one myself) who freely weigh in on matters from where I went to college and what major to pursue to how to raise my kids. It’s hard to tune out those voices but I do find that it becomes easier the older I get, especially when I read advice like yours. Thanks.
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- June 1, 2011 at 1:23 pm
- Felicia Shelton
- Said...
What a post and so on time with what’s currently going on in my life.
I just returned to the States after having completed my contract in Seoul, South Korea. The easy thing to do would be to return but in all honesty I’m hesitating about returning. On the one hand, it’s the easy thing to do, I know the job, the drill, etc. but on the other hand I want to take a break from teaching or at least teach in a new country. I love to travel and now I’m beginning to get more and more gigs as a photographer from different magazines. It’s strange, the easy way to get to other countries is to teach English but on a full time schedule it leaves little time to work on my photography which is what I really love to do. I’ve lived around the world and want to continue doing this but as a photographer. What I’m thinking of doing now is choosing another worldly city in regards to my work as a photographer. The question is how would I support myself fully because I’m used to not sweating over housing, food, and other essentials while in the new city. Oy! In a way, I think your move is amazingly simple. You’re moving there due to your husband’s career, all you have to do is pick where you want to live, then set up house…in England. You’re going to love it! Congratulations! -
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- June 1, 2011 at 1:26 pm
- Felicia Shelton
- Said...
Wasn’t trying to trivialize your research into different neighborhoods in England, just want you to see you’re so lucky, but I think that you know that. I’m very happy for you!
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- June 10, 2011 at 2:49 am
- Felicia S.
- Said...
Just read your last comment and I think that’s a great idea. I was working on it yesterday. I have to be prepared and I that I’ll use today and this weekend to strategize and be more than prepared next week, when I’ll set out in several neighborhoods that flourish with the kind of businesses I would love to shoot or otherwise be a part of in a creative way. Thank you so much, Jennifer.
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- June 1, 2011 at 3:14 pm
- Heather
- Said...
Great advice Jennifer! It generalises to any decision really. I wish you well in your new adventure!
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- June 2, 2011 at 9:22 am
- Brooke (Books Distilled)
- Said...
Jen, thanks so much for this article! After I read the guest post on your site by Stacey Curnow, I started trying to figure out how to quit my job! The only thing I could think was that I really wanted my old position back (sadly, it’s four states away). So I brainstormed a list of projects I could work on remotely, and my old boss was thrilled to give me some contract work! You never know until you ask.
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- June 2, 2011 at 4:28 pm
- Bryce Christiansen
- Said...
Hi Jennifer,
That’s amazing you found a place to live in such a short time frame, but it makes sense when you use the guidelines above.
Your post reminded me of the videos I’ve been making the past couple of weeks that go through our assessment reports.
One of the values people have is aesthetic. People with high aesthetic motivators are affected by their surroundings and work environment significantly. We’ve helped a number of clients who realized that was one of their top values and they call us up thanking us when they find their next job and they took their surroundings as a serious consideration for the job.
It’s a true point you make and I just wanted to second it.
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- June 2, 2011 at 9:08 pm
- Jennifer Gresham
- Said...
We thought it was pretty amazing too–that’s what got me thinking about the process. Once I saw the connection, I had to share of course!
Thanks for adding your perspective and experience. Always appreciated!
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- June 4, 2011 at 9:13 am
- Vanessa
- Said...
Jen – this post struck a chord with me, especially the part about choosing between two fairly equal options. I really struggle with decision making sometimes, so worried about making the wrong choice. Sometimes I second guess my choice but generally after agonizing I make the right one. But then I always wish I made it sooner.
The well intentioned advice about people giving advice that justifies their choices is so true. I’ve been guilty of this myself, although not so much in the context of careers. I’m going to try and be more aware of this in myself and be mindful with others.
The list of criteria in a job are spot on – I feel like bookmarking this post for future reference. Thank you for being so generous with your words of wisdom and all the best in your new London adventure!
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- June 4, 2011 at 9:46 am
- Daria
- Said...
Yay! Congratulations on the move and also on the flat choice. Sounds wonderful that you already have friends in your neighborhood and connections to the community. So happy for you! AND your post is great and very timely for me, so thank you – again – for some really great, tangible, advice.
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- June 6, 2011 at 5:52 am
- Andrew Hill
- Said...
Jen, thank you for an interesting narrative about decisions and how we arrive at them. I can certainly relate to your indicators of job connectedness and the sense of well-being (or not) that work may sustain.
With respect to significant problems and decisions, sometimes snap decisions must be made according to what we know at the time and our present emotions and feelings. For other decisions, I think it is important to gather objective information and comparisons first. That can help us to contextual and evaluate our feelings about present circumstances and possible futures.
I think it helps to alternate the rational consideration of alternatives with periods of mindfulness, by which we let go of the problem for a while. There is a lot going on below the level of consciousness in mind and body and it best to let those processes take their course. I have often reached satisfying decisions that way.
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- June 6, 2011 at 10:35 am
- Dawn Lennon
- Said...
Jen,
What an amazing experience and perfect comparison. I apologize for being slow to get to this great post and comment.
You make so many fabulous observations here, so it was hard to pick. But I do love your point about how so many never call it “work sweet work.” We would all be so much happier if that phrase became our overarching career goal!
It’s your observations about the adjectives that were so exciting and revealing. I had never thought of adjectives as being the real clues to making our career and other best decisions. This line is so true:”Before you consider working at a company, ask them for the adjectives they think best describe the culture and working environment.” I can think of many situations where my adjectives we polar opposities from my bosses.
Then this observation really struck a chord:”Sometimes you find your people, sometimes they find you.” So true and so important. It should give us all comfort.
Well, you’re in for another amazing adventure and endless content for your blogs. Thanks for sharing your insights. They are amazing. ~Dawn

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I’m 53 and have finally after 30 years on / off in the workplace found the job that makes me do the happy dance. And have finally found the town and house that makes me feel the same. How? By ignoring the advice of others and listening to what made my heart sing – great post today about finding a career that fits – and that can also be applied to finding a life that fits, too. Thanks for sharing your gift of writing.