When to Quit.

May 23, 2012


It’s been almost 2 years since I left my dream job as senior art director at my old advertising agency – but I can still taste the anxiety that decision left me with.

So when Ramona, an aspiring creative entrepreneur, emailed me for advice about leaving her current job for another job that is a bit more of a creative challenge it was a no-brainer that she should do it – but I know first hand how much emotion can cloud your perception when it comes to weighing the pros and cons to make such a bold decision.

I want to share with you all my email correspondence with Ramona where I help her break it down. Even though Ramona’s circumstances are specific (and those specifics should be considered even when following your heart) I think it could potentially help a few of you who are struggling with the decision of when to quit too.

From Ramona:
Subject: Taking the risk to following your dreams or staying safe???

Dear Kathleen,
I have been reading your blog for quite a while now and you truly inspire me when it comes to starting your own business, following your dreams and the such. I am writing your today for advice as I find myself in a situation where I have to make a pretty tough decision.

So here’s my story: I graduated from university in 2009 with a degree in International Business Management. I have been working as an assistant for the CEO ever since in a small company doing regional development and marketing.

At first I was challenged, had my own projects and was able to grow. But now I am bored most of the time. Yes I get a good paycheck at the end of the month, but I do not accomplish anything – I have to add that I am the kind of person who needs the challenge. I always want to grow and move forward. If I’m really in it, busy (in a good way) and challenged I become really creative and I work harder than anything. But I haven’t experienced this in a long time. I have of course applied for new jobs in communication, marketing, events but so far nothing has worked out so far.
My dream has always been to be a freelance one day doing creative consulting and events and weddings and maybe development help in 3rd world countries.

I know my time to be a freelance has not come yet. But… here’s the thing. I go to a church here and they opened up a public restaurant/café last October. It’s seriously a great restaurant and one that’s offering foods that do not exist in this region where I live yet. It’s very stylish and always displays local artists and it’s cozy and the food is truly great! Sadly, it’s not running the way it should be yet due to lack of leadership from the manager. Last week the owners sat down with me and offered me the position as restaurant manager. They told me that they believe that I can manage and lead people, that I would bring a heart and a vision and creativity in it that could turn this thing around and make it to the place it could be.

Wow… I was pretty overwhelmed and honored and scared I guess. I have no experience whatsoever with leading a restaurant. Like nothing. Plus, I would for now get less money than I do now and my time schedule and everything in my life would change.

If I’m honest with you I have always looked up to women who followed their dreams no matter what. Who got out of their comfort zone and just did it. They were passionate and made it happen. I’ve always wanted to be that kind of a woman. I do believe that if I take on this job it would be one step further to being a freelance one day as I would learn how to run a business. It would be great challenge and a great risk. Yes, running a restaurant sounds fancy and I often romanticize everything in my life and dream a fairy tale. I do know it would be hard work and busy schedules. I just really want to accomplish something in my life. Not for the money or for fame, but for myself.Isn’t now the time to be risky and go after my dreams and just get out there and do it? Follow my heart and dream?

I know I am totally writing you all this personal stuff and I don’t even know you but I wanted to ask you because you seem to be the person who did it and you know how much work it is. Do all my thoughts make sense to you? Do I sound a little weird just telling you all this?



My former life as senior art director at a really rad ad agency – it was a tough decision to leave. Photo by David McNeese.

Here’s my repsonse to Ramona’s dilemma:

Hi Ramona!
First off, I’m really flattered that you thought of me as someone to come to for advice. It really means a lot! I don’t have all the answers but I have been in the position of making hard career decisions – so I would love to share my point of view on it all.
Reading through your email it seems as if your main hesitations to jump ship come from: A) Money, B) Lack of Experience, and C) Fear of Change. I would like to address each of these and break it down so hopefully it’s a little less scary. 
I’m going to start with Fear of Change because this is the one I know best. I remember very clearly when I was thinking about leaving my ad agency job to go freelance that I was most terrified of making the wrong decision and stepping into the unknown. I was fraught with anxiety that I was killing my career and for what? In hindsight, I am clear that there is no such thing as a right or wrong decision. If you insist on moving forward in life you won’t ever make a wrong decision – because it just doesn’t exist – but only if you use every experience as an opportunity to learn. Making a decision at all (and then actually executing on it) is the hard part. 
I think a nine-to-five job with a steady paycheck provides us with a certain amount of security but the truth is things can always change at a moment’s notice. Consider this: what if your boss was planning on closing up shop or letting you go tomorrow what would you do? You would probably consider it a blessing and take the job at the restaurant. The only difference is that someone else made the decision for you. Be brave enough to make your own decisions
Along with being afraid of change – I was also terrified of the unknown. Here I was feeling like a spoiled brat because I was leaving my dream job for uncharted territory. I felt inexperienced and had no concrete picture of what freelancing would look like – and that was scary. This turned out to be a blessing because it meant I could decide for myself what that would look like. I think the same will go for you. You will be able to manage this restaurant the way you see it. Because you have no experience you may bring a certain amount of creativity and individuality to the job that no one else could. My advice is to be transparent and honest in this process. Authenticity will bring people who want to help you succeed to the forefront. 
And here’s another secret I’ve learned in life: Beyond a little bit of training and education, EVERYONE is making it up. Nobody is born a business owner or manager or killer designer. You’ll figure it out as you go – and that’s the beauty of it. 
While I’m a huge advocate for creative entrepreneurs doing their thing I’m always hesitant to tell anyone to quit their nine-to-five (before they’re ready) because of the money issue. Nothing kills creativity like not being able to pay your bills. That’s just the truth of it. But in your situation at least you’ll still be making a steady paycheck – just a little less than you’re used to. However, it sounds like the trade-off could be worth it. I think as long as you can still pay your bills the money issue isn’t much of an issue, for now. 
Obviously, you can ask your employers for a raise as you bring some life (and organization) back into the restaurant. But more importantly, if your end goal is to work for yourself, I would consider how your new role as a restaurant manager is adding to your expertise as a creative consultant and event planner. I would also think about how you could begin to build your business on the side. Put together a portfolio of weddings & events you did for friends and start charging for your services (even if it’s just a little bit at first). You’ll feel that much more confident when you finally make that leap as well. 
It sounds like, for you, the decision has already been made. Quit your job and follow your heart. I say romanticize the restaurant and hang on to that fantasy – that’s what will make you a successful (and happy) manager even when things are tough. And know that this decision isn’t permanent – when it’s time to move on again you’ll move on.


What do you guys think? What advice would you give to someone in Ramona’s position?

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