There have been three pivotal career transitions in my life.

Each time, I become enveloped by a deep desire to go do my own thing. It’s an insatiable hunger that pulls me back to the place where I suppose I ought to be. I’ve tried desperately to make it easier, to go a more conventional route. But like I tell my clients, “Wherever you go, there you are.” (thanks Jon Kabat-Zin).

I’m a boss.

Now with that bossiness and inevitable ownership comes a deep commitment to do whatever it takes. Turns out that can actually be really hard and even require unglamorous compromise (preview on that below). Each of my career shifts seem to be another climb on the monkey bars of my own personal growth playground. Every iteration allows me to become a little more of who I want to be.

This is my career growth pattern. Zero to making things REAL. It’s an obsession with creating, building and growing things. It fulfills my need to feel challenged and engaged by a high level of variety.

I love it so much that all I do now is help other people create or optimize personal brands, build a side hustle or hack their corporate career plans.

Anytime I deny what lights me up for too long, I start to acquire other toxic patterns in my life to compensate. There is a threshold where feeling disengaged from my work literally makes me feel like my soul is dying. So in the end it’s not much of a choice for me. Consequently, I’ve had to figure out how to make it work each step of the way. There’s no one perfect scenario and I’ve found it really takes a lot of time, work and adjusting the puzzle pieces to build the scenario that integrates most of your personal and professional priorities at the same time.

Corporate is not “bad” and entrepreneurship is not “good.”

Being your own boss isn’t a total dreamboat.

You are still you, wherever you go to work. So that piece of self-awareness needs to get rectified first.

The clarity around your true values and priorities paves the way to get on a professional track that enables you to actualize the life you crave. Next it’s figuring out what your top skill strength is and strategizing an efficient way to meet the above criteria then take that next available step.

Maximize it and continue to move forward.

I want to reiterate that I believe there is great wisdom in enjoying your life, remaining emotionally unattached to your job and simply clocking in to make money. I totally admire that.

That’s just not the career conversation I am trying to have right now.

I am wired to want to bring my creativity, soul, intellect and the essence of who I am into my work and I tried to live in all the rationalizations of “having flexibility” and “getting paid well” and “work is work” dance and I just couldn’t stay at the party.

I have chosen to make my day job a vehicle to forge a greater connection to *feeling* emotionally, mentally, physically and spiritually engaged. *If you are a FEELER type this alone may help you clarify your career path already.

No career path is perfect. This I know.

But there is a level of inner congruence we can find that aligns our values, skill strengths, and lifestyle preferences rather harmoniously. It’s been worth it for me to continue my quest and commitment to make this convergence possible for myself.

Although I’ve had great and not so great experiences on all sides of my personal career path – full-time corporate, hybrid entrepreneur and corporate, and full-blown entrepreneur – I still arrive at the same place.

I want to feel that I have choice in my career contributions (where I invest my time and energy, and the end results of my efforts).

I want to be capable of making money doing my own thing.

I want to be the CEO of my life and my career.

Here is how I’ve zigged and zagged between Coaching and Corporate career gigs over the last 10 years and what I have learned from it.

Career Transition 1: ROGUE
“I must pursue my passion.”
– Jeanne circa October 2007

Transition Style: Quit cold turkey

Job/Role: Healthcare Investment Bank

Timeline: 11 months

Breaking Point: My uncle mailed me a book titled “You Quit But Your Boss Doesn’t Know.” Sheer misery was clearly written all over my face.

Exit Strategy: Cliff-jumped out of corporate to pursue my passion

The Vision & Quest: Deep yearning to work in the professional coaching industry since my teens (shout out to Oprah and Cheryl Richardson!)

How’d I Do It: Walked in, quit cold turkey with little preparation. Emailed every Executive Coaching Company in NYC and got an unpaid internship with the head of a Private Coaching Business. Moved from Boston to NYC, lived with my 84 year old grandmother in Yonkers. No paycheck, no home, no set plan.

Career Transition 2: READY
“I must create a real and viable business.”
– Jeanne circa October 2010

Transition Style: Quit after investing and working with a private coach to create an exit strategy

Job/Role: Executive Recruiter for top 20 Venture Capital backed start-ups

Timeline: 3 years

Breaking Point: Three months in I knew this was not the job for me, but I needed the perks, time, and pain to get me to my next turning point.

Exit Strategy: Used my steady paycheck to subsidize an investment in working with a Career and Wellness Coach.

The Vision & Quest: Burning desire to make money doing work I felt passionate about and wanting to be on my own schedule. I wanted to work at the intersection of wellness and business and ultimately have a say if I wanted to do yoga at lunch.

How’d I Do It: Instead of quitting cold turkey and having no paycheck, I decided to use every extra cent of my paycheck as investment money towards my passions and personal development. I hired a personal Coach and invested in a Coaching Certification Program. With my Coach, I crafted an “exit strategy” to practically shift towards my own business venture. I invested in someone who had the business and lifestyle I wanted, which expedited my ability to run my own business more successfully.

Want what they have, do what they do 😉

Career Transition 3: REVOLUTION
“I must share my gifts, skills and experience in a bigger way.”
– Jeanne circa October 2016

Transition Style: Quit after a year of training through my professional skill gaps

Job/Role: First person to run Sales & Business Development for the 24th office of the largest creative & marketing staffing agency in Connecticut (28 offices nationwide).

Timeline: 1 year

Breaking Point: I quit after investing in specific skill development (operations) and when things were “going well.” I figured it would be smart to get paid at what I am good at (sales) and trained in what I sucked at in my business (operations). A company that’s scaled from 7 to 28 offices and sold for around $500 million had a lot to teach me. I was earnestly open to staying with the company, but in the end my heart called me back to a full-time focus on my own brand.

Exit Strategy: Patience. Perseverance. Planning.

The Vision & Quest: I must share the value of what I know about career transition, brand and business development to help more people move through their own career shifts (platform launching 2017!).

How’d I Do It: Despite some egoic freak-outs of leaving my full-time entrepreneurial world and major resistance on the job, I decided to let life be the CEO for a little while. I felt burnt out from hitting the growth phase of my private coaching business, and failed to transition to a more scalable model. I needed to be led and be a student of sales, operations, and financial management. It was really hard in many ways and a lot of work, but it groomed me with the skills necessary to take my brand to the next level (here we go!).

A Few Lessons:

1. Investments are essential. Choose wisely.

Know why you do what you do.

Where the hell did we all get the notion that we could have our career dream overnight? Let me advise you that building your career requires years of skill building, learning, failing, spending too much, not doing enough of much or wasting everyone’s time bitching about your boss for too long. For those of you who found your thing and have stayed with it for 10+ years, this blog is not for you but rock on! For everyone else on their entrepreneurial path, I suggest you audit your investments (time, money, skill growth) and align appropriately. It starts with honesty and self-awareness. What is your current role fulfilling towards your top priority (creative expression, money, lifestyle flexibility)? Why are you choosing this if you feel miserable (no judgement)?
You are either going to invest time, money or certain lifestyle preferences (it can be difficult to actualize the perfect symphony of all three all at once – I have yet to see it). Super successful people seem to be working their ass off behind the scenes for years investing in their craft before they get “big.”
So this literally means that you might make $20-40K, you might invest $10K+ in mentors and programs, you might need live at your parents’ house, or Airbnb your place on the weekends. You might need to take a job that is “way below you” or you might need to stay at your job that makes you “feel successful to others” and endure the internal daily emotional torment. How do you want to pay?

2. Do what’s appropriate for YOUR needs, values and skills at each turn.

No one else knows your journey, only you know where you need to go.

That may look like sticking with something that’s not ideal. As long as you are clear about why you are where you are, what I call Work For Purpose, then you can cope, knowing it’s a temporary turn to gain a skill, save more money, or give you the suppressive tension that will only make you crush it when you’re out of that daily gridlock.
Audit yourself and your business with utmost honestly. Take a piece of paper and on the left hand column write “What Is Not Working” and on the right hand column write “Why It’s Not Working”. Basic place to start.

3. Enjoy the learning, the flailing, the triumph – all of it – and live on the way there.

The joy is in the journey.

Looking back, there were so many volatile moments through each transition because life was still happening. Break-ups, moves across the country, re-building and deconstructing apartment after apartment. Paying taxes I didn’t plan well for and other fun stories of mismanaging money. The cost of my transitions were often highly financially, emotionally and spiritually taxing, and yet they are at the core of what puts me in a position to write this. I only attempt to share what’s been true for me, and I only offer one point of view to take along your own unique journey. You will likely get there if you are relentless at doing the one thing you’re always the best at. If you’re persistent you’ll check that box, and if you’re consistent you’ll likely keep it for a while. You might stay on one track or you might zig-and-zag like me, focusing on just what you need along the way to become an integrated professional. The spiritual insight that I’ve come to see is that no one really cares that much and it is just a career. If it’s a big one then you’ll have a big career. If it’s not, then you might not have a big career. Either is OK and all that matters is how the experience feels and what results you are looking for in exchange for your investments.

The only life that matters is the one you want.

Cultivating this understanding is the most vital career strategy of all.

Thanks for reading 🙂