Ugh. I Did It Again.

by | Sep 26, 2017 | Blog Posts, Decision Making, Transitions, Uncategorized | 9 comments


I’m feeling disappointed and a bit lost as I wake up this morning.

I’ve lived in Chicago for eleven and a half years now. It’s an amazing city and I’ve been happy here, but I’m starting to feel ready for a new place and a new adventure. I’m starting to think that I want to move in the next few years.

A few months ago, my boyfriend and I started brainstorming what we would want in another place if we were to move: warmer weather, open minds, good restaurants, an arts scene, access to good doctors, and some major headquarters where my boyfriend could work as a corporate accountant.

As we brainstormed cities that checked those boxes, Raleigh-Durham rose to the top.

Neither of us had ever been there but, from our online searches and from what people said, it seemed to be everything we’d listed.

All summer, I’ve felt my excitement growing about Raleigh-Durham…even though I didn’t even understand if they were one city or two.

As June, July, and August passed, the story I told myself about utopian Raleigh grew.

I noticed it happening. I cautioned myself from starting to feel certain about anything before visiting, but it’s a very human tendency. In the absence of real information, we tell ourselves stories.


I flew out to Raleigh early last week to check it out. My boyfriend met me there later in the week.

I’d booked two Airbnbs in different popular neighborhoods in Raleigh, and another Airbnb in Durham.

I was so excited to get to the first Airbnb, drop off my bags, and check out the first neighborhood.

To my surprise, it was centered around a small three-block stretch, with everything interesting on one side of the street.

Coming from Chicago (the third most populated city in the US and the second densest city in the US), when I got to the Krispy Kreme at the far side of the three blocks, I was confused. Where was the rest of this cool neighborhood?

It was a cute stretch, with a couple of acclaimed restaurants, a wine shop, a beer shop, and a fabulous small bookstore that shares a space with an architecture firm…but it was definitely not what I was expecting.

Oh, yes…that lesson again. Expectations set us up for disappointments.

It was what I’d told myself all summer as I built up my fantasy of Raleigh.


It’s interesting to have this experience as a transition coach. I’m a career transition coach, but the concepts still apply.

That day and the next, over and over again, what I found in Raleigh was totally different than what I’d imagined.

Don’t get me wrong. Raleigh is a solid town with the nicest people. My boyfriend and I ate and drank really well, and had fun talking to the locals. (Definitely check out Bida Manda, Brewery Bhavana, and Dram & Draught when you go.)

However, in the end, I think we both learned that we want a city with more density in its downtown and neighborhoods.

We headed to Durham (or “Durm,” as they say it there) on Friday morning and spent the long weekend there. (Raleigh and Durham are indeed two separate towns, about a half-hour apart in no traffic.)

We really liked Durham. (Check out Rose’s Meat Market & Sweet Shop, Ponysaurus Brewery, Bar Virgile, the Bobbit Hole Trail at Eno River State Park, and the amazing Saturday morning farmer’s market.)


Durham actually checked off all of our “boxes.” It still feels a bit too small for this big city girl, but it feels denser than Raleigh and is definitely growing.

Durham can stay on the list, but we want to check out some other places, too. (Nashville, I think we’re coming to you next.)

As a career transition coach, one of the most important parts of my work with clients is to help them really explore the top options that they’ve brainstormed. It’s a step that often gets skipped (because it takes more time), but it’s super important.

Without doing what we can to confirm that our idea of a place (or career) is based in reality, it’s likely that we’ll end up disillusioned and disappointed, perhaps enough so that we have to start the job (or city) search over from scratch.

I’ve made big changes, with not enough research, before.

About ten years ago, I went to culinary school because I wanted to make a career change. I didn’t want to be a theater actor and to have to have a “day job” to pay the bills anymore. (That’s a longer story for another day.) I loved cooking and it seemed like the only feasible idea for what I could do next. I went to culinary school and became a professional cook, only to soon realize that professional cooking/the restaurant industry weren’t for me, for a lot of reasons.

That was one of the most dramatic and difficult lessons of my life. It was embarrassing to make a career change and then quickly realize that I didn’t like my new career. That step also cost me a lot of time and money.


I don’t believe in mistakes, but what would have been different if I’d taken the time to deeply explore what it means to be a cook before signing up for cooking school?

What’s life like, in and out of the kitchen, when you’re a professional cook? What does it feel like to cook for perfect degrees of doneness, pretty plating, and speed, instead of for pleasure and community? What’s it like to be a 30-something woman entering the industry? What kind of life does being a professional cook set you up for down the line, personally, financially, and otherwise?

What would have been different if I dove into those questions, and allowed myself to see and examine the possible risks or unattractive sides, instead of just plowing forward because it was the only possibility I could see for myself at that moment?

I might have avoided being back in the same position, wondering what on earth to do next, just a couple of years after making the decision to go to culinary school.

We’re not just going to pick up and move to Durham tomorrow.

We’re going to take more time to brainstorm more options.

Since I can work remotely, I’m going to get to each one as soon as possible…so I can explore what each one is really like, instead of building up a groundless, beautiful story of what our life would be like there.

If we’re still considering Durham down the line, I’d want to rent an Airbnb there for a couple of weeks, or even a month, to get a deeper feel for what it would be like to actually live there.

If/when we do move, I think we’ll rent for a year, so we can make sure we love our new city and so we can pick a neighborhood that suits us.

I want to take time to explore before entangling myself in a way that makes it hard to get out.


I keep thinking of the saying, “Look before you leap.”

It might take more time, and that might feel frustrating, but thoroughly investigating our options can help us avoid unnecessary headaches and heartbreak.

Talk to me….

Are you thinking of moving or changing jobs?

What does my story make you think?

Also, what cities do you love and think we should check out?

Please post in the comments below!

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  1. As a Chicagoan who has often thought of moving across the country and a former chef and career changer, I enjoyed this story quite a bit.

  2. Sheila, this is a wonderful story and reminder of many things!
    I recommend you check out Denver…I will be moving there soon, from Montana.
    I have been there many times over the past few years (at different times of year) and recently spent a week there, checking out neighborhoods and seeing how I was with all the traffic. Born and raised in London, UK, I have lived in Livingston, MT for the past 25 years. I am truly ready for city life again and loved finding my way around in major traffic at different times of the day including rush hours. I deliberately drove 100+ miles each day to get a feel for it all. I made several acquaintances in that short week and can see myself making friends there as I move forward.
    Wishing you well in your search for a new city to call home. I believe we grow so much through the places we live.

    • Hi Barbara. Good for you! I’m so happy to hear how thoroughly you’ve been investigating Denver. It sounds like it will be a wonderful step for you. I’ve actually never been there and have wanted to go. I checked out your website. You have quite an amazing career path. Will you continue your business coaching in Denver?

  3. Hi Sheila, came across this via Chris Guillebeau and I’ve gone through very similar life changes. I chased the job though and didn’t think this hard about locations. Since I didn’t want to go back to school for a second career, I took a series of internships (to build work experience) in extremely remote locations that taught me so many hard and beautiful life lessons, not to mention how adaptable and strong I could be. A big city girl too, I was born and raised in the burbs outside Chicago and then moved to LA after college. Experiencing these new locations in real time is so important to the process. You can certainly do what you are going to do… stay in a town for a month to see how it goes… but for me, after several months is when the reality of a place sets in, perhaps even a bit longer. “I wonder what it’s like to live in a small town” is something I don’t have to wonder anymore because I lived it, 3 times over. To be honest, I feel the same way you felt about R-D as I do about Santa Fe and all I did was spend a single night there. My solution is that I’m currently building a tiny house on wheels. That way, I can just roll away if it’s not for me. Check out Designing Your Life, a great book that talks about proto-typing your big moves first, before jumping. Thanks for sharing your story 🙂 I hope you find what you are looking for in a city.

    • Hi Jenny. Thank you so much for sharing your story with me. Are you really building a tiny mobile home??? Do you have pics? Also, I love your pics of Oaxaca. I’ve been wanting to go!

  4. This is very timely for me. I am leaving my company. Nearly 11 years and setting off to be a working nomad. I have a couple of marketing contract jobs in the Works but taking time to explore what type of work I want to do and/or explore. I am also going to start my journey in Thailand for about 6 weeks and return to the states for an event in July and re-evaluate. I can relate to your approach in choosing new cities. I’ve always been a nomad at heart and want to start for a couple months and see if it’s what I think it’s cracked up to be. Thanks for sharing your story! And I hope you checked out Nashville! It’s a great city. That’s my hometown although I’ve now been in dallas for 7 years.

    • Hi Robin. I’m excited for you. Congratulations on taking a big step. Have a wonderful time in Thailand. I have so many friends who have loved exploring that country. (Also, if you’re ever interested in connecting, let me know. I’d be happy to set up a no-pressure complimentary call to see if my coaching interests you. It can be really helpful to have a career coach to ask the crucial questions — and to reflect back what you’re saying in a way that makes what you want crystal clear.) All my best to you!


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