Kicking Your Career Change Off Right- Happiness Project Style

I know I’m about 8 years late to the party (story of my life), but I’m REALLY digging Gretchen Rubin’s book “The Happiness Project”. It is rocking my world right now, just in time for the New Year. For those who are unfamiliar with her concept, Rubin chose 12 areas of her life she wanted to work on throughout a year and spent a month on each area.

By the way, I’ve started video blogging over on my Facebook page here, (“Like” the page to get notified when I go live and post video tutorials and all that jazz!) but after staving off 13 people’s colds, three stomach bugs and my husband’s full blown flu three weeks ago, I have finally succumbed to Sickness-Palooza 2016/17, so with my Rudolph-esque nose, I think videos are a no go this week.

Anyway, back to Gretchen. While her way of approaching things and her perspective is similar to mine in some areas, it’s radically different in other areas, which got me thinking: I bet we all think about career changes or pivots in wildly different ways, with wildly different attitudes, ranging from “I GOT THIS” to “NO, PLEASE, MAKE ME DO ANYTHING BUT GO TO A NETWORKING EVENT!” to everything in between.

SO, as I was reading her “Work” chapter, it hit me that lots of her lessons are SO vital to career change that I’d be remiss NOT to write this post. So, without further ado, here are some of the critical lessons from Rubin I think we could all consider as we enter a career change or pivot in 2017:happiness







Image: Happiness: A Happy Dog Contemplates Life In the Woods on New Year’s Day

  1. 1. In order to have more success, you need to be willing to accept more failure. Happiness doesn’t always make you feel happy. Wow. This one was huge for me. As I looked back to consider my career change, I can pinpoint the few times I actually felt happy during it. I mean, I worked three jobs at one point to have some income while I built my business. I had months of $1200 or less in income. I had a ton of debt as I built and invested in my business and my skill set. I worked for a CA-RAZY company at the beginning of my career change (the one I mention that I don’t even put in my resume) that made my additional schooling all the more stressful. You get the deal. My career change was (and still is) fraught with risks and potential failures. Some came to fruition and others never did. So when you are considering your career change- or maybe you’re in the thick of it and feeling a little all over the place- know that it is normal, and that to really achieve that next level, there ARE inherent risks and nothing’s a done deal, but nothing is irreversible (besides questionable tattoos) either.
  1. Your Inner Critic Can Be Your Bestie, of Sorts. And no, not necessarily the margarita and taco night bestie, but more the friend who tells you like it is and doesn’t sugarcoat the message. What the heck am I talking about here? When instead of believing what your inner critic says about your abilities to change careers (“you don’t have what it takes”, for example) you can use that as information to KEEP.GOING. Acknowledge that this is your Inner Critic talking and keep going. If you want to get anything accomplished, you need to keep pushing ahead without constantly second-guessing yourself. So, terrified of networking meetings and think you bombed your first one? 1) you probably didn’t and 2) in order to hit on something big, strike a chord with someone, learn to present yourself better, you just gotta go out and do it again, and again until you start to hit your stride.
  1. When You Feel Rushed for a Solution, Slow Your Roll. When I’m trying to figure something out for the first time, I get all anxious like I need to know the answer right away or I’ll spontaneously combust. Like today, my assistant sent over a new program to help us keep track of passwords better (ummm if passwords are the bane of your existence like they are mine!) and I just HAD to know how to do it RIGHT THEN AND THERE. But…ya don’t, I promise you. So, if you’re embarking on your career change and feel like you just gotta know what your actual next step is RIGHT NOW OR ELSE, ya don’t, I promise you. Trust that you will figure out a way. When Rubin feels anxious and that she needs to know X now, she “puts herself in jail” which means that she tells herself she’s locked up with nowhere to go until she figures out a way to slow down. She also tells herself that it doesn’t matter how long it takes; the end result is that the project (in this case your career change) will get done.
  1. Work Smart. I talk about this in the Career Change Kitchen online course. It can’t be stated too many times. If you say to yourself, ‘Well I have all day Saturday to write some networking emails to start gathering info for my career change,” chances are it’ll be suddenly Saturday night and you’ll put your dancing shoes on and head out the door. Instead think about setting a timer (I suggest 45 minute work blocks) and focus on one SPECIFIC task. So with the networking emails, maybe you spend 20 minutes making a list of people you’re going to reach out to with their email address, 15 minutes drafting an adaptable email that can be tweaked per person slightly and 10 minutes sending the first one or two.
  2. Flip the Script: OK here it is: NOW is the fun part. I know, I know, a hard pill to swallow when you’re starting to put yourself out there in ways you never have before, so hear me out. The challenge for happiness, Rubin writes, is to take pleasure in the ‘atmosphere of growth’ – in the gradual progress made toward a goal. This brings in another concept I’ve been using a lot for clients and students of the Career Change Kitchen (and myself too!), and that’s Todd Herman’s idea of the WOW versus OWW Brain way of thinking. OWW Brain people look at accomplishments in terms of how far they still have to go and WOW brain thinkers look at accomplishments in terms of how far they’ve come. A very small yet huge distinction. SO, as you contemplate how to enjoy the career change process, try to think about it in terms of how far you’ve come. Maybe you’re just getting started, but making the decision to actually start after years of contemplating it is a huge deal. And then, as you rack up ‘wins’ in the career change process, you’ll note that doing a little something pretty often starts to stack up to bigger wins, and a WOW brain mentality is further cultivated.

Ok phew, that was a lot, but I hope at least one of these ideas re: happiness and career resonated with you as you start to contemplate or are going through a career pivot or change. They really are game changers once you put those mental hats on.

I talk about many of these concepts and more, as well as how to implement them in the Career Change Kitchen online course, a course I developed to help you achieve career happiness- in other words, helping you change your career in a soup to nuts way with way less anxiety and second-guessing. I’m guiding you every step of the way. You can check the course out here. I’m hosting a free info session on 1/9/17 and you can snag your spot here.

The Three Crucial Areas To Focus On When Exploring Potential Career Paths


Imagine the scene: you, tired of your role in event planning, have done some exploring and decided that a career in either graphic design, digital marketing or as a horseback riding instructor would really suit you, but you’re not sure where to start exploring. So, you start by checking out all the usual job boards, see what’s available and start applying to all three because “you might as well cast a wide net and see what comes back, right?”

Wrong. And I don’t normally like to use that word, since there are SO many ways to look at any given situation.

But seriously, wrong.

If you’re in marketing or work with marketers, you’ll appreciate the following phrase: If you try to appeal to everyone, you appeal to no one. Every brand out there has their ideal customer (sometimes referred to as an avatar). Nike, Barkbox, S’well bottle, Bai Tea….and YOU, when you’re looking to change jobs or careers, are a brand too.

This means that before- yes, before – you seriously consider any job description and DEFINITELY before you apply to a single job, it’s critical that you thoroughly explore each of your career options and consciously decide on ONE to put yourself in the running for.  In other words, just so we’re clear, in this hypothetical example, you’re choosing between graphic design, digital marketing and horseback riding instructor (hey- anything goes in Jill’s wacky Career Change Kitchen, so go with it!)

So, where are the three places to look in order to fully flesh out each of your options so that you can come to this conscious decision?


Surprise! Online plays a big role in the beginning of your exploration process. You don’t want to hang out TOO long here, so what I recommend is setting a timer for exploring for 45-60 minutes PER career path. So in our hypothetical example, you’d set 45-60 minutes aside for graphic designer, 45-60 minutes aside for digital marketing and 45-60 minutes aside for horseback riding instructor. Avoid the rabbit hole at all costs! You want to get an idea for your basic questions about each of the roles here- you’re not trying to solve whether this is the career for you. Before you dive in, make a list of those questions so you also can protect against rabbit-hole-isms.

Also, bookmark any online seminars any associations, trade groups, or networking groups are providing and pencil them into your calendar. Most, if not all professions have a trade group or an association and those can be good places to search for resources, info and seminars where you can learn more about what people in the field are talking about.


Yes, I’m talking about going to live, in person events. These can be seminars, workshops, panel discussions, networking events—the list goes on for this exploring phase. I don’t necessarily recommend spending $2k + on an industry conference at this stage, per se. Instead search for networking groups in your area that have free events or reasonably priced. In NYC, for example, I’d say anything under $35-$40 for a 2-3 hour event is reasonable, but you also really need to assess the value. Are people that you would want to meet and learn from going to be at this event? If you don’t know, ask the event organizer.  Don’t go on a blitz of moderately applicable events; instead pick the 1 or 2 that will really allow bang for buck (and time and energy! After a long day, you want to at least be semi excited about this!). Check out industry associations and see if they’ll let you check out an event before joining. Be bold!


Dun dun dun! Yes, the third piece of this is to actually speak to humans while exploring career paths. Real. Live. Humans. I know, I know, but it’s going to be ok! You’ll want to look into your own network to see who you might already know (score!), who people you know can introduce you to (so 2nd degree connections) and people you clicked with at the aforementioned events above that you can set up follow up chats or meetings with to learn more.  You also might reach out to some random people whose profile on LinkedIn matches what you’re looking for. (OMG JILL NO!!!!) But seriously. This is the sweet spot of where you can fine tune your exploration and research phase and really dig into the nitty gritty of a role (“Hey, so what’s it like day to day being a graphic designer?”) and to really get a sense for whether your skillsets, interests and values/priorities fit that field.

No, talking to one person for a rushed 15-minute conversation as you’re running to the subway after the event, racing home to catch Empire (no? just me?) is not sufficient. Part of this is about relationship building and part is about learning more about the field.

No, talking over email to one person does not count.

This part is gonna be a little gut-checky and might make some of you feel a little uncomfortable. But one of my favorite people and closest biz confidants always says, “Being wildly uncomfortable is where the growth is.” So are you ready to come out on the other side of this, ready to grow? Let’s get started!

Oh, and after you do all of this? THAT is when you can develop your job search materials (LinkedIn profile, resume, etc) and start applying to jobs. NOT before.

Resistance: ACTUALLY Do Something You Want To Do

Why we allow resistance to prevent us from doing what we ACTUALLY WANT TO DO when it comes to work and life has been of major interest to me lately.

I’ve been pondering things like, you know, why I was checking my email 43 times a day (Luckily I have won the war on Facebook and IG, turning off my feeds) rather than DO THE WORK or why I’d suddenly feel the need to dust every wood surface of my home office with pine-scented wood cleaner rather than DO THE WORK. Anyone who knows me knows I really can’t stand most forms of cleaning, so I sure as heck didn’t suddenly gain a new hobby.

By way of background,  “DO THE WORK” for me means something pretty specific. I’m not lounging around in my pilates outfit eating wasabi peas all day watching “Veep” (Ok, ok, Last Tuesday, you win). Instead, I’m working with clients, writing blogs, speaking at and attending events, incorporating my business and the like. What took me awhile to realize was, that although those activities felt good and productive (and some of them ARE needed), they were…just activities. They weren’t actions toward my ultimate goal. Which, for the record, is to build a suite of online courses to help my people out AND to create international retreats. Instead, they were exactly what I called ’em above- “activities”.

And then I looked around and I saw people resisting everywhere- clients, friends, family, colleagues, people who call me for my complimentary consults– many of us are resisting the very thing we WANT to be doing.

It struck me as nonsensical so I set out searching for answers. I was open about it with some friends and colleagues and Aidan and a friend and I were talking about it when she recommended The War of Art, by Steven Pressfield. 


The aftermath of a WIN Symposium dinner party where I talked about resistance.

As soon as I started reading it, I knew I had struck gold. Pressfield REALLY digs into the reasons we don’t do what we say we want to do and he gives us a framework through which to overcome aforementioned Wasabi-Peas in Pilates Pants Consumption. He says in many different ways that many of us are truly aligned with a path – we know what we’re meant to be doing- but we do LITERALLY EVERYTHING ELSE besides that one thing. This was essentially me for the month of April. I was super responsive via email, even more attentive than usual to clients and colleagues….and yet, nothing got done. What gives?

Some key takeaways:

Am I A Writer?: (Or a painter, or an entrepreneur, or a whatever it is you are). Self-doubt can be an ally. This is because it serves as an indicator of aspiration. It reflects love, love of something we dream of doing, and desire, desire to do it. If you find yourself asking yourself (and your friends), “Am I really a writer? Am I really an artist?” chances are you are. The counterfeit innovator is wildly self-confident. The real one is scared to death.”

I’ll Get Started Once I Overcome My Fear: “The amateur believes he must first overcome his fear; then he can do his work. The professional knows that fear can never be overcome. He knows there is no such thing as a fearless warrior or a dread-free artist.”

Fear of Criticism: a professional doesn’t take success or failure personally. Evolution is all about biological factors. It’s in our cells to worry about rejection. The amateur uses fear of rejection to prevent us from doing our work or showing it to the public for public consumption. To take rejection personally is to reinforce resistance- the battle is in our heads, not with critics or reviewers! It reinforces resistance again and again.

Knocking the Notion of Unlimited Choices on Its Head: This one is the kicker for me. Oftentimes as a career coach, I’m asked if I can transition anyone to any type of career. The answer is no, and not just because of the skill gaps one might have to fill before going toward a particular career (that is a totally workable situation for my work with my clients) but more importantly, it’s because we’re all not meant to do a huge number of things. (Despite my love for cooking, for example, I am NOT meant to do anything with sharp knives like work in a kitchen. Ask my college roommates and my doorman in Buenos Aires who had to get me to the ER in 2012.)

Which brings me to this idea. Whether you agree with it at its core or not, the idea of resistance is a very interesting concept to think about what you’re meant to be doing and your duty to breakdown the resistance and do it:

“Another way of thinking of it is this: We’re not born with unlimited choices.

We can’t be anything we want to be. We come into this world with a specific, personal destiny. We have a job to do, a calling to enact, a self to become. We are who we are from the cradle, and we’re stuck with it.

Our job in this lifetime is not to shape ourselves into some ideal we imagine we ought to be, but to find out who we already are and become it.

If we were born to paint, it’s our job to become a painter. If we were born to raise and nurture children, it’s our job to become a mother.

If we were born to overthrow the order of ignorance and injustice of the world, it’s our job to realize it and get down to business.”

So…what’s the takeaway of this article- how DO you overcome resistance to do what you actually want to do? We’re going to get to that next week, so for now, the takeaway is to sit with some of these ideas and let ’em settle in. Next week we’ll discuss strategies.

In the meantime, if you’re tired of doing nothing about what you wanna be doing, let’s chat on one of my consults. You can sign up here. 

Lessons Learned From My Day With “Drunk History”- Career Edition


For the first time in nearly two years, I got sick. Admittedly not my best quality, I’m kind of a whiny sick person (See, “Calling my mom who resides 100 miles away asking her half jokingly, half seriously that I need her to ‘fix this’”).

Anyway, the world slowed down figuratively (and literally, if you take into account my Nyquil haze), and I had to take a pause. So I did what anyone would do, and I binge-watched Comedy Central’s “Drunk History”- Seasons 2 and 3. And this post is about the lessons I learned. Well, lessons learned above and beyond how good Jaleel White was at playing American hero Bass Reeves.

IMG_3670 copyOrnament from the Ozovek-Rosales family tree. I thought it was fitting. (Photo credit for sideways photo I can’t seem to rotate: Jill Ozovek)

  1. There are no bad ideas. I mean that. Obviously not every idea is a viable career path or business idea, but many of those core ideas can be developed to something viable. Whoever thought that drunk comedians and people telling the stories of historical figures is a genius, but I bet it didn’t start out as it is now. It took finessing, testing, re-finessing and retesting. So, my point is, go start a “Drunk History” spinoff in the UK. No, my point is that if you have an idea for something you’d like to do for your job, but you don’t think it exists yet or isn’t something you can access, try your very best not to extinguish that light/passion. Maybe it doesn’t exist because you’re ahead of the times and there’s something you can do now that does exist. Or maybe it doesn’t exist because it’s not viable. Do your due diligence, talk to people, expand your network- do anything but let it go from the get-go.
  2. Let your freak flag fly. In other words, be yourself. It’s gonna be exhausting to put on a show in an interview or getting to know you phase (in a networking or business partner sense) and then have to keep up that façade foreverrrrrr. I haven’t met and interviewed the creative geniuses behind “Drunk History” (yet), but if I had to guess, I’d say they didn’t compromise who they are or their vision for the show. Same thing goes for when you’re starting a new thing and are looking for clients or you’re looking for a new company to call ‘home.’ Many times, people come to me saying they’ve tried everything and no bites have come their way and they can’t make any progress. When we lift the hood and do some mock conversations, it turns out they’re not being authentically themselves. People say it all the time and it can sound trite, but being authentically you is THE key ingredient for success. You need it no matter what. As Oscar Wilde used to say, “Be yourself; everyone else is already taken.” Companies are looking for robots less and less these days, I hear.
  3. Narrative is key for a viable candidate/idea. I’ve been beating this drum for awhile but it is TRUE. Understanding your personal narrative (Check out my online class on this here) is crucial to connecting to both your target company and job description. Without it you might as well not apply. Funny you should ask- the same goes for “Drunk History”! Their genius format has the audience following three different stories constructed over a major theme (e.g. “Cleveland”, “Journalism”, “Games”) and they carefully curate each of the 3 stories to fit in an approximately 7 minute time frame. It’s tight, compelling and leaves you wanting more- exactly the three things you need when pitching yourself for a job or pitching an idea to potential clients or investors.
  4. Let the things around you inspire you. Ok, so I didn’t feel this way yesterday (see: aforementioned Nyquil Haze), but let the weird and wacky or the beautiful and exciting things around you inspire you to try something different or try to do something you normally do differently. It inspired this blog post, for example, and maybe it will inspire you to watch the show. Or something. What I’m really saying, though, sarcasm aside, is to let whatever is around you in your day to day life inspire you to try something new. Maybe you’re sitting there thinking that every day is the same, blah, blah, blah and if that’s truly the case and you’re just not putting up blinders, try to spend some time in the slower holiday season to do something inspiring for yourself! (If you like food and going to weird new places, hit me up for my next Walking Food Tour- Holiday edition in December). You never know what will click.

Ok, I think I squeezed enough out of my day watching “Drunk History” for this blog post. If this was helpful and you want to spend some time figuring out what that passion piece is for you, click here for a tool to help you. And if you have questions about it or want to discuss, give me a shout here.


The Topic on Everyone’s Mind This Week

No, I’m not talking about the NYC Pizza Rat (although, gross). Nor am I talking about the 30 pound burrito challenge (although, intriguing).

I’m talking about balance. And before you roll your eyes and say, “That’s impossible,” or “What is she going on about now?” (said in a British accent), hear me out.

First of all, when I say ‘balance’, I don’t mean everything is hunky dory in all aspects of your life. Nor do I mean you are essentially holding a million balls in the air in perfect balance and the strain is killing you. A balanced life shouldn’t feel like a constant struggle. It shouldn’t feel like, “One wrong move and it all comes toppling down- dun dun dun!” It should feel….easy. (And no, not ALL the time, every SECOND, but overall.)

Why am I noticing this topic this week? 

1. It’s literally on every client’s mind. (OK not literally- that’s impossible). Every client I have spoken with so far this week and end of last week has mentioned balance in some way shape or form. Someone I just started working today pinpointed it as her #1 criteria / priority for her life.

2. Social media is abuzz over it. A colleague of mine posted this on Facebook: “Researching full-time jobs and am kind of flabbergasted by the number of companies that require nights, weekends, holidays, and even availability “in December and January with no special time off” (taken word for word out of a job description with a reputable brand). Why is zero work-life balance not only the norm but the standard now?”

49 people ‘liked’ it and there are about a dozen comments so far and counting.

Additionally, whole articles are being written on company culture at places like Google, Zappos and the like and how employee happiness and engagement is paramount.

3. There is a craving for this kind of personal or inner work and development. Whole companies are cropping up over it. (Check out Mindvalley Academy for one such group- maybe a great place to be EMPLOYED at, huh?)

So, with so much interest and intention around having a balanced life (which oftentimes seems to stem from having a balanced professional life rather than the other way around), why are there so many craptastic companies to work for and what can you do about it so you don’t end up at one of those?

1. Ask the right questions. I did this exercise with my 30 Day Bootcamp last week– think of culture questions to ask that are not, “So how’s the culture here?” Things like, “What’s the difference between a good employee in this role and a great one?” can give you a glimpse into whether the company’s values are aligned with yours. “How do you onboard new employees and how do you handle beginner mistakes?” could give you insight into how supportive a company culture is. Pro tip: “We don’t think people make beginner mistakes” or “We hope people don’t make them,” is not the answer you’re aimin’ for.

2. Research! Glassdoor is of course a great tool to see employee reviews, but not every company is on there slash getting feedback from a human you know or know through someone is better. Make sure you have specific questions before talking with someone. Also, know your parameters/non-negotiables before heading in. What will you or won’t you tolerate? Would the job description referenced in my colleague’s post above- long hours and weekends and holidays- be amenable to you? Get specific.

3. Know Your Narrative. Yes, yes, that pesky topic I keep talking about AGAIN. Know your story- where you’ve been and where you’re heading – so that you are only going for companies that are a match for your specific case. A lot of times we end up at crappy companies because it sorta relates, but not really or we’re not sure how it relates, and we don’t pay attention to red flags because we JUST WANNA JOB DAMMIT….you see how it can go. But knowing what you want, what you don’t want and how to craft questions to determine fit will go MILES and MILES toward you finding that balance. If you want to learn more about how we can work on your narrative together, go here. 

4. The Lever Approach. Lastly, let’s incorporate a little of the rest-of-your-life into this post. It’s the lever approach and one I started using recently, albeit a little late. I’ll give you a personal example to demonstrate.

For anyone looking at my life currently on paper, it’s insane. Lots of amazing work, clients, business opportunities- and that’s just work. Some family stuff is taking priority as well as my relationship with my partner. But I don’t feel insane overall. Yea, there are moments when I’m a little rushed, but I gotta say- they’re few and far between.

It’s because other levers in my life are dialed way down for now- namely personal development classes that I like to go to, social engagements and friends. They’ll be there when I’m back! (By the way, the first time i used this lever approach, it was tough to let go, but the benefits are so worth it that it’s easier and easier to do.)

So in closing, I’m not saying, “Follow this recipe and you’ll achieve nirvana and bliss!” but instead, play with some of the ideas above and see what works for you over time- and let me know how it goes!

Want to talk about any of this? Maybe a way to put some of this in motion for you? Sign up to chat for a brainstorm call here.