[caption id="attachment_9094" align="aligncenter" width="450"]businesswoman desk macbook Photo by Bench Accounting on Unsplash[/caption] “It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly.” – Theodore Roosevelt

Quit Your Job? Are You F@%king Crazy? 

I stared at a postcard in my bathroom that I bought for myself which said: “Room to Dream," wondering what else was out there for me. Something better? Was there more freedom? More creativity? More of being ME? I would daydream about the notion of having space to work on my own shit (as in my limiting beliefs) and hopping on a magic carpet ride to somewhere that I could be my best self and do really impactful work. Yes, I was contemplating the very difficult question of, "Should I quit my job?" I was not in a reality TV show and there were no cheerleaders telling me to take the leap into the unknown of my own potential. People don’t egg you on to go take a risk – not even your biggest fans. In fact, people think it’s their duty to advise against leaving a job without something else in hand. They project all their fears onto you because they themselves haven’t found a way to believe there is another way. Trust me though – there are a lot of people out there in Corporate America dreaming of something different for themselves. There are numerous data points that talk about workplace satisfaction (or the lack thereof) and the negative effect it has on employee engagement. In fact, according to Gallup, 70% of workers are NOT engaged in their jobs. So why do we think we should listen to those unhappy people to help us figure out how to be MORE fulfilled and satisfied in our careers?! Consider this: the Bureau of Labor Statistics estimates that 15 million people were self-employed in 2015. Keep this fact in mind the next time you are considering someone else's council. Think hard about the advice you are receiving, the person who is giving it to you, and the scare tactic picture they are trying to paint. Weigh all your options for living your best life. Bottom line: sniff out the bullshit. So here I was, considering leaving my six-figure corporate job without a clue about where I would get my next paycheck. After a decade of strategic moves, interviews, and clawing my way up the ladder, I found myself standing at the edge of the abyss,  wondering, "How the hell did I get to this place?"

Hanging on and Letting Go

Alright, let me break it down for you. Every move I made in my career, every promotion, leap to a new company, shift in industry and function, had a reason. And I extracted every ounce of lemonade from every lemon project, ray of light, and drop of opportunity. But, at this particular juncture, the lemon itself was on life support. A confluence of things happened at the same time; my passion was shifting from marketing to corporate culture and coaching, company dynamics were shifting to a place of contraction versus growth, and I was turning 40 in a year. All reasons that would make someone question the purpose of life… This stage of my life was compounded with a broader context: trying to fit into an outdated model of what makes a good leader. For 15 years I navigated my career by molding myself into whatever box my current company or boss wanted. By swallowing my words more than I spoke them. By making tough choices about when to stand up for myself, versus let things go. By holding onto the fibers of my true being despite the lack of leadership role models, all in order to reach the next rung of the ladder. Over the course of 15 years, I felt my wings were clipped more than they were encouraged to fly. A small voice inside my head told me I could soar higher if not for the comfort of big-company resources and the louder voice in my head that was limiting my belief system. The moral of the story here is that the prevailing mentality is that staying on your trajectory is a safer, better place to dig in your heels. It is difficult and courageous to deviate from the "plan." How many times do people urge us to just go and try something different? When anyone goes against the grain of societal norms, there is likely a storm going on inside, regardless of what financial stability exists, even after the decision is made. If you are considering leaving your job, ask yourself the following questions and go deeper still to fully explore them.
  • Are you in a toxic environment? Are your mental health and overall well-being at stake?
  • Are you able to live your values with integrity?
  • Have you explored every avenue to extract value and learning opportunities?
  • Are you running from a problem, or boldly walking towards a new vision for yourself?
  • Are you running out of fear, or walking tall in your full power?
  • Is a short-term sacrifice worth a long-term gain at this juncture of your career?
  • Do you have the support to make this choice feasible?
  • What are the fact-based data points around the financial feasibility of leaving?
  • What are your inner critics saying to you?
Once you've answered these questions, you'll have a better sense of what you are hanging onto and what you want to let go of.

Get to Know Your Inner Critics

I reached the point where I had to take a leap. I knew this wasn’t a situation where I should just “get the next offer” to inevitably stay on the same path. I knew I had to break my pattern of playing my life safe. It was time to tear up my outdated printed playbook, which was influenced by who I used to be, rather than who I was becoming. I had to plunge into the world of my inner critics because, while my heart knew my truth, the rest of me was on a much different page. Voices in my head sounded like parents, mentors, old bosses, ex-boyfriends, and expectations from society at large. I heard these voices while I was in the shower, on the subway, in meetings and watching TV. I had to intentionally separate these voices from what I really thought. I will never forget the moment I broke through that barrier. One of my coaches at the time (oh yes, I needed all the help I could get) asked me to tell her all the reasons why I shouldn’t quit. I blurted them all out with tears in my eyes, except it wasn’t my voice I was hearing. When I finally paused, I realized that I didn’t believe anything I had just said. I was on autopilot, reading from the same script that had been read to me over and over again. If you want to get to your real truth, especially when facing a big life decision like leaving your job, get acquainted with your inner critics (yes, that was plural) with these steps.
  • Gain Awareness: For at least a week (ideally two), write in a journal every time an inner critic in your head says something to you.
  • Separate the voices from yourself (they are not you!): When you hear those inner critic statements add the following words to the beginning: “My inner critic is telling me that…”
  • Create characters for your inner critics: Have some fun with this. Draw a picture of what that voice looks like to you. Give it a name (but don’t use any family names). Provide a description of that critic. This will help you see that your critics are NOT you.
Does this sound scary? Yup, it sucks. BUCK UP. This is the REAL work of your life – learning how to push the limiting beliefs out of your life so your real dreams, hopes, and aspirations can come to the forefront. No one can do this for you. No amount of reading books will make it better. Dig in, dig deep, and learn about who you are behind all the noise that's been holding you back.

Taking the Leap, Now What? 

Even after I made my decision, I had to take a few more steps. I gave myself a deadline to meet so I would actually hand in my notice. I even told a few people about it to give me some accountability. I had to accept that I was going into the unknown and was about to face a range of reactions. I also knew I would feel better about my choice if I committed to starting a coaching certification program to ground me with the “what” of my life as I entered the gap. When I gave my notice, I only told the people in my life who I knew would give me high fives and lovingly call me a badass. It was a vulnerable time and I didn’t want to subject myself to haters! I also wanted to give a consistent message about why I was leaving and what I was heading towards because I wanted to own the path that I was building for myself, even if I didn’t know how it would all turn out. Here’s an abbreviated “to-do” list for when you decide to take that leap of faith:
  • List of all the things you are walking towards, including how you want to feel, who you want to be, opportunities you want to chase, and growth you want to experience – so you can go back to this list in moments of doubt.
  • Clean out your office a few weeks before giving your notice, to help you make your decision feel real before you say goodbye.
  • Decide how you want to leave – with what mindset and with whom you want to spend quality time with before you go.
  • Have an anchor for how you want to use your time once you leave – whether that’s a training program, a vacation, a project you intend on tackling, or a list of books you plan on reading.
  • Determine the soundbites you want to leave with people before you put in your notice.
  • Plan to celebrate your courage and bravery with those who supported you on your journey.

One Year in the Gap and I Would Do It Again

Let’s not get it twisted here. While I have been fortunate enough to spend time in the gap – my journey this year has not exactly been filled with cupcakes, unicorns, and endless brunch dates. I have taken this year to give myself a good hard look in the mirror, to shift into a new way of being, and to dedicate myself to healing old wounds. It’s amazing how much I’ve had to unlearn and learn; like how to unlearn living inside the structure of 9-5 and how to learn to live in a state of flow, creativity, and flexibility. I’ve had to unlearn how to define success and learn to create new ways to see my value. I’ve also had to learn how to listen to myself first (not last) and accept that my intuition is a powerful force to leverage rather than dismiss. I’m also continuing to understand what self-compassion looks like and that self-care is so much more than getting a massage every so often. To respect and honor my needs and desires is a way of being. This gap year has come with miracle moments and dark times. Trust – I spent plenty of nights with a bottle of wine as I witnessed friends get fantastic new jobs and I wallowed in the uncertainty of still “figuring it out." I have to remind myself that I dedicated this year to growth and adventure so that I could be my best self in service of others – in whatever capacity I choose to do so. One year later, almost to the day, I have just signed on the dotted line to have my business website built from the ground up. To create a hub for my hopes and dreams and unleash MY full potential. To believe and embody that anything is possible. Maybe it will end up working out or maybe it won't. Either way, I know that I will always choose to be in the arena and to live this life as fully as I possibly can.


Tosca DiMatteo is the Founder and CEO of TOSCA Coaching and Consulting, which she created to help inspire and support individuals and organizations in discovering/re-discovering the heart of their brand, so they can live it authentically from the inside out. Previous to this, Tosca spent 20 years honing her badass marketing and collaboration skills in the Consumer Goods, Media and Retail industries. You can find more information on toscadimatteo.com, Facebook, and Instagram    

The Gap is Rampant: You Are Not Alone

Oh, the gap. The gap between here and there. Between the old job and the next gig. Between the old you and the new you. I have a pin on my desk that says “f#*!k," and that just about sums up the employment gap. But alas – there is a way through this, a way to THRIVE in the chasm. To embrace it, to love it and to fully live in it – for in the grand scheme of life, in time, the gap will be but a sliver, a blip on the screen that will be part of the pixels that make up your life. And the gap could very well be one of the experiences in your life that brings you closer to yourself. Before diving into the “how” of thriving in the gap - let’s just talk a bit about why this is happening, because, my friend, you are not alone. Gone are the days of 30-year tenures and pensions. Disruption has hit (or will hit) just about every industry. Restructures, layoffs, emerging skills, and jobs going overseas are part of the current career landscape. As a result, layoffs have become almost a rite of passage. On top of this, job descriptions are changing, because needs are changing. Truth be told, many companies don’t know what they need or what they will need in the near future. The icing on the cake? Even with all the shifts, recruiters and hiring managers are still using the outdated paradigm of trying to put round pegs in round holes. And yet, through the rubble and chaos comes the rising phoenix – the reinvention. And THIS is the beauty of the gap. For the gap is a temporary place between where you have been, and where you will be. It’s the place between who you have been and who you want to be. To embrace this place, it’s critical to own your truth.  

Your Path is Yours: Own It and Talk About It

In our society, so much of our identities get wrapped up in our job titles and careers. The sooner you can own the answer to “what do you do” or shift the conversation to answer the question “who are you becoming” – the more comfortable you will be in social situations. Owning your story is one of the first steps towards living in the gap authentically and unapologetically. Owning it might mean allowing yourself to grieve the relationships and the activities you are leaving behind. Owning it might mean allowing yourself to feel the fear of not knowing what’s next versus giving in to the fear and being stuck. Owning it is taking your power back by not letting shame hide any longer, by telling the story that YOU want to tell. As a marketer for over 15 years, trust me – I know a little something about storytelling. And you get to tell the one that’s in your heart and that gets you excited. You are the shero in your own story. What do you want people to know about your gap that feels authentic for how you want to tell it? To get started, think of your story as an experiment – because your story has so many ways it can be told. Test it out on everyone who will listen and know that the more people you talk to, the more comfortable you will get. Being in the gap is so much easier with support and a team. So for those of you who like to crawl into a hole until you “figure it all out,” pay close attention to this next section.  

Put Your Team Together: You First 

So you finally owned your damn truth…CONGRATULATIONS! Now it will be much easier to own that you have some real work to do. The work of reinvention. In my humble opinion, this has two components. First and foremost is getting back in touch with your #1 contact, the one with all the answers, the one who matters most…YOU!! This whole opportunity that I am speaking of for truly reinventing your life, means you have to get in touch with yourself in a way that you perhaps never have before. If you are with me on this, then I offer you two pieces of advice for dialing into your own inner wisdom. The first is to sit with yourself with no distractions and listen to what arises. Listen to your own guidance on what you need. The answers often come in the form of a whisper, so you have to really get quiet and truly listen. The second piece of advice came up time and time again when hearing stories of people who learned how to thrive in the gap – is to work with a coach. For full disclosure, I am a coach – so I clearly have a point of view on this. But as someone who has been in the gap twice, I wholeheartedly believe, and my interviews have confirmed, that having a coach can help you see the forest through the trees. A good coach can help you rediscover yourself, offer you new ways of looking at your situation, and support you in believing that anything is possible. They are not a friend who has a plethora of opinions to share, but a partner in helping you determine where it is you are wanting to go. A coach helps you get aligned with yourself, and not with the opinions of others, or society. When you find the right fit for you and what kind of coach you need, the investment in yourself during a time of transition and doubt can mean the difference between just surviving the gap versus being transformed by truly embracing the gap. This brings me to my next point, which is that as you embark upon this big project of figuring out “what’s next," then PLEASE for the love of all things chocolate, put your team together. Don’t go on this trip alone. Who do you ask? Who should you have on this team? It might look different for everyone but start by asking yourself what you need. Some of the things you may need include a shoulder to lean on, inspiration or the need to feel healthy and strong. You may need insight into a new industry you are investigating or an unbiased perspective on your approach to figuring out what’s next. You may need to feel needed and to get inspired. All of these things are perfectly normal. So who can help you with these things?  Gather the troops, whoever they may be, and don’t forget about those whom you don’t know yet. The more you can connect with the folks on the outermost circle of your network, the broader your thinking will be. And your potential for meeting people with very different experiences than yourself will grow exponentially. I think it’s important to note that it might be a good time to evaluate if a therapist should be on your team. Karen Carlucci, a licensed therapist, and certified professional coach suggests considering the emotional impact of landing in the gap. "For some folks, suddenly not having a traditional job can create self-doubt, shame and a lost sense of identity. It may trigger past experiences that are unresolved around self-esteem and worthiness for instance. Therapy can help with understanding these triggered responses and offer ways to work through the current experience in a supportive setting." So, who are you going to recruit for your team?  

Handle the Truth: You Are Not in Control 

There is no magic bullet. Life is not linear. There is no set path. And no, Google Maps does not have directions for you. You may be in the driver’s seat, but you really have no control over when your gap ends, or where it will lead. The sooner you can surrender to the process, the sooner it will be possible to enjoy being in whatever moment you are in. Thriving in the gap is more possible when you allow yourself to live in the moment. And just to clarify – I mean YOUR moment. People around you may be getting job offers and accepting jobs, they may even appear happy and un-phased by the gap. Fight the urge to play the comparison game; this will not serve you because everyone will have a very different path. Every baby step you take is movement in a forward direction. You can’t possibly go backward. Every action propels you forward. So how can you handle the truth?
  • Truly accept that whatever led you to the gap happened FOR you, not TO you.
  • Take nothing personally.
  • Keep on putting one foot in front of the other – following what feels aligned to your truth.
  • Surrender – because the outcomes are not in your control.
  • Celebrate all your small wins – let the light shine on them so the feeling can grow and invite more wins into your life. That’s the secret to building momentum!

Join the Club, Get Social

The experience of the GAP reminds me over and over to never underestimate the kindness of others. I have been astounded at how many strangers have accepted my request to connect. Put aside the inner critic in your head that is shaming you for not keeping in touch with people. It’s bullshit. Reach out because you don’t know what you will discover, and I’d bet that they will want to hear what’s up with you. And if they don’t – on to the next!! Give it a try. Go be amongst your peers or the peers that you WANT to be yours. It’s a learning curve to figure out what makes sense to attend and where you will find value, but it is definitely worthwhile. Part of this strategy involves setting realistic expectations about what success looks like. In fact, I suggest setting goals that you have control over. For example, rather than set a goal of finding five job leads, instead set a goal around how you want to be and feel when you walk out of that event. Thinking about this process as a marathon and not a sprint and keeping in mind that finding meaningful connections takes time will help you think differently about how you are measuring success when it comes to re-igniting or building your network. Bottom line? The home office can be a lonely, lonely place, so get off your butt and meet someone new!  

Enjoy the Journey

I would be remised if I didn’t acknowledge that your financial situation, as well as other kinds of privilege implications, can play a big part in embracing the gap as an opportunity. I invite all of those realities to be a part of your process and also invite you to focus even more on the mindset that will best serve you in staying positive, hopeful and being your best self. As my good friend Vishwas reflected to me about his career shift from Marketer to Actor; “happiness is in the doing, not the outcome." Dig deep in yourself and understand what truly makes you happy, what excites you, where you add value and figure out how to be still. Travel, see friends, visit family, and eat food that brings joy. Investigate ideas that are bigger than your career and that are bigger than you. Gain a different perspective so you can look at your journey in a way that allows you to enjoy as much of it as you possibly can. This isn’t the complete guide to thriving in the employment gap, but it is a start. Being in the employment gap IS hard. But it can also be one of the most reinvigorating and rewarding times of your life if you open your heart and mind and surrender to not knowing.


Tosca DiMatteo is the Founder and CEO of TOSCA Coaching and Consulting, which she created to help inspire and support individuals and organizations in discovering/re-discovering the heart of their brand, so they can live it authentically from the inside out. Previous to this, Tosca spent 20 years honing her badass marketing and collaboration skills in the Consumer Goods, Media and Retail industries. You can find more information on toscadimatteo.com, Facebook, and Instagram