Career Transition Confessions

Career Transition Confessions

“Sometimes life hits you in the head with a brick. Don’t lose faith. I’m convinced that the only thing that kept me going was that I loved what I did. You’ve got to find what you love. And that is as true for your work as it is for your lovers. Your work is going to fill a large part of your life, and the only way to be truly satisfied is to do what you believe is great work. And the only way to do great work is to love what you do. If you haven’t found it yet, keep looking. Don’t settle. As with all matters of the heart, you’ll know when you find it. And, like any great relationship, it just gets better and better as the years roll on. So keep looking until you find it. Don’t settle.”

Steve Jobs Stanford Commencement Speech


This post is dedicated to anyone age 40+ faced with life or career challenges.  Those who are overwhelmed.  Those who feel like everything you try to get ahead ends up being a day late and a dollar short.  Those who feel like you never win.

This post is for those who may find themselves living back home with their parents, today.  Those who lost a job, lost their way,  had no plan, or you just flat out failed.

It is for those who feel like you no longer have valuable skills that fit the marketplace. Those who, quietly, fear they are too old to keep up and learn 21st century skills.

This post is for those who struggle to form meaningful alliances in the marketplace. Those whose self-doubt season their conversation to the point of self-sabotage.  Those whose follower count don’t prove enough worth to attract influencers.

Finally, this post is for those looking for hope and inspiration to reinvent themselves, press RESET, and try again!

So be warned, some parts of it may read like an episode of Iyanla Fix My Life. 🙂

“I’ve missed more than 9,000 shots in my career. I’ve lost almost 300 games. 26 times, I’ve been trusted to take the game winning shot and missed. I’ve failed over and over and over again in my life. And that is why I succeed.— Michael Jordan

The Question 

How did I go from an always side-hustling administrative assistant, to commercial real estate agent, to real estate bookkeeper to virtual digital marketer? Well, it’s kind of a long story.  A lot of that story is found in a post I wrote, last year, about my BOSI Entrepreneurial DNA profile.   But the short of it is–I’m just a late bloomer to discovering what I’m good at and what I should be focusing on to earn a living.

A Bit of Back Story

I’ve always had a vision for what I wanted my life to look like–since a child.  But, over the years, I’ve been unsure of which lane I should take to get there.

Whereas many knew what they wanted to be/do as a child or had some sort of vested guidance as a teen (or young adult) helping them find their ONE thing–life dealt me another set of cards.

  1. I, first, had to concern myself with surviving (aka just get a “good job” ).
    1.  I was an 18 year-old country girl in a new big city (Atlanta) with no family support.  No family support not as in abandoned me, but as in they were not able.  So, my first goal, at 18, was to get a  “good job.”  My good jobs were secretarial and administrative in nature.   It wasn’t until I had an encounter with God, at 21, that my eyes began to open to broader possibilities and I began to think bigger.
  2. I’m curious, multi-skilled, and multi-passioned–a blessing and a curse.
    1. I think in terms of possibilities. Then, I go try what I determine is possible.I’m always thinking–how can I kill two birds with one stone. How can I accomplish more than one goal with the same effort?  I can’t shake this type of thinking.  For relative to the ladder, my intent is efficiency.  But to my chagrin, I, often, end up an inefficient multitasker–which has cost me more in time than in wins.


Trial & Error

Consequently, I’ve been learning my career path by trial and error.  And, I’ve been, totally, okay with that.  For, I gave myself permission, long ago, to take my time to explore my vast interests so as to learn myself and gain skills.

I saw too many unhappy and disappointed people on the back end of having taken the “traditional routes.”    So, it was pretty easy for me not to let the pace at which others, around me, arrived at their life goals–rush me.


I’m over 35 and is just, now, getting a strong sense of what I should be doing with my life.  I, finally, feel confident I’m on the path to the purpose and lifestyle I envision.  I’m, finally, doing what wholly interests me and I’m pretty good at.

By the way, special thanks and shout out to Gary Keller and Jay Papasan and their book, The One Thing.  It’s really given me the clarity to help me get a handle on my chronically, inefficient, multitasking problem.

The One Thing Papasan Keller

Who Am I Professionally?

While working in the real estate industry, off and on, since 2003, I side-hustled, functioning as a business and marketing strategist for my own entrepreneurial experiments.

It’s only been revealed within the past year that I should have been pursuing a career path in marketing. I started on this path, briefly, assisting an Atlanta PR Firm in my early 20s.  But, I was not emotionally mature enough to handle all that opportunity required of me.  Funny how life circles you back.  There is a saying that goes,  “God will keep bringing you around the same mountain until you climb it.”



Negative Self Talk

I was professionally confused.  For in my mind, I was a bootleg marketer.   I mean, I’m, only, using pre-designed WordPress templates.  I’m not a real web designer.  Yeah, I know how to manipulate and place code but only as instructed by a real designer.  I don’t know how to write code.

And as to marketing, yeah, I sold an idea or two.  I persuaded a handful of folks to believe in my idea to the point of actually forming a company, getting a business bank account, and a beta version of the idea(s) to market.  But, those ideas bore no fruit.

Sure, I created a couple websites on my own to test my ideas.  But, I got no significant traction.  So, how in the world can I credibly consider myself a “marketer” when my efforts to market my own ideas have been so unsuccessful?  I’m, clearly, still figuring this out.  People want to hire (and believe in) experts NOT someone still figuring it out.

Sleep copy

Aha Moments as Truth Emerges

Unbeknownst to me, at the time, those thoughts revealed a mindset of fear and defeat.  I was shooting myself in the foot.  I was, totally, missing the forest for the trees.

First, I didn’t notice how extraordinary I am to have been able to conceptualize, package, communicate, and present as many entrepreneurial experiments I did in the past four years.

Second, I, unnecessarily, frustrated myself concluding I was unfocused because I had too many ideas.  It’s, now, dawned on me that a marketer is supposed to have that many ideas.  Different clients need their marketers to have many, many, many ideas.  Duh!


The irony is I would have so many ideas and think, “I know they can’t all be mine.”  In other words, all this time, I did not know that, entrepreneurially, I’m a marketer.  Or, assistant right hand to Rainmaking, high-growth entrepreneurs.

All the trial and error has brought me to the precipice of my true creative and entrepreneurial potential.

I was all in the weeds of the hair industry trying to create a business, for myself, when I should have made my business finding businesses in the hair industry to market.  Consequently, those past experiences weren’t the failures I concluded.  They were just lessons.



What My Imposter Syndrome Sounded Like Over The Years

Between 2004-2007, I closed $6M in multifamily real estate transactions and still didn’t think of myself as a successful marketer.  My short win felt more like a stroke of luck rather than real skill.  For, like with everything–with me, professionally, I’m always the new kid on the block, learning as I go.

I’m the one fumbling my way into the end zone instead of scoring with finessed skill.  Because I don’t look my age, people underestimate me A LOT.  And although I’m assertive, it’s not my nature to force my way.  Also, I’m very transparent with people. I’m uncomfortable faking it until I make it.  And, sometimes that hurts me–professionally.

I had a client tell me, once, that more experienced agents approached him, often, to suggest he ditch me and choose them.  He refused citing he hired me for my heart and hustle and wanted to give me a chance.  And guess what?  I closed that property (final price tag $1.5 million dollars).  

But somehow, at the time, it didn’t quite register how dope that accomplishment was of me.  In my mind, I was an inferior agent because I fumbled my way through. This and other experiences I had, during the 2007 market downturn, deflated all my enthusiasm for the sales side of real estate.

Fast forward ten years to what I described above.   Although I have hard evidence of marketing and selling ideas, I’ve been, quietly, feeling like until my efforts produce an engaged audience or revenue for my clients or myself, then I’m not really an effective marketer.  Period.  For, the proof is in the pudding right?

The Truth 

Again, do you see the defeated mindset in all of that stinking thinking?  Do you see how hard I’ve been on myself?  What if God knew where I needed to begin and presented these small marketing opportunities to establish a record of work and some easy wins?

Although my primary purpose for pursuing sales was to gain knowledge to position me as the investor I envision, the truth is I did exceptionally well for a rookie.

I exceeded my own expectation.  I discovered a bit of what I’m made of.  And, I, certainly, believe I could have gone further in sales had I not talked myself out of it and found the right support system.

My first day in real estate school, they said over half the class would not last as an agent one year.  I lasted three years and with above average closed sales.

RESET Mindset 

It all begins with mindset.  What in the world have I been thinking–you ask?  I honestly, don’t know.  My stinking thinking is just an outworking of my weaknesses and emotional deficits.  But here is the strategy I employ when my thinking threatens to betray me. It is how I pull myself out of these low places, often, right before I cut my nose off to spite my face. :).

  1. I stop everything and start a 3 day water-only fast.  This purges the body and negative thinking. It triggers a sudden reset in focus.
  2. I turn off my phone and disengage social media.
  3. I turn my attention to God–mega dosing on prayer, worship, gratitude, and bible study.
  4. I seek out opportunities to focus on others by praying for them. I solicit prayer requests to divert attention away from excessive self-concern while remembering God’s mercy and grace to me.
  5. I double down on my daily schedule and focus on getting stuff done vs. self-doubt.
  6. Repeat 1-5 until I feel a sense of clarity and breakthrough.

Capable of More

You must address your mindset so you can notice and identify your wins–however small.  The more I entertained self-doubt, the more it kept me from seeing the power of my small wins.  For, they revealed the possibility that I could do more–be more.

For example, five years ago, I would have laughed at you if you suggested, I would one day be interested in learning to code.  The very thought overwhelmed and repulsed me.

That’s something you pay super smart tech people to do. I don’t code.  I pay coders.  Well, today, I’m totally confident that I can and will learn basic HTML, CSS, and Javascript in order to become more competitive as a marketer.



Finally In My Lane

July 2016, I called forth courage to believe in my business talents and skills.  I decided to stop flirting with my future and market myself as a digital marketer to the industry I know well–real estate.

Within a couple weeks, I had a real estate agent as my first client.  Within a month, I had the small brokerage she works for as a client.  And within the same month, I was hired by a digital marketing agency as a freelance marketing consultant to service their dossier of clients.

I have NO college degree.  I don’t, yet, code.  I just have raw marketing talent, good ideas, a teachable spirit, courage, and determination to not give up on myself and what God has deposited within me.

Encouraging Moral of Story

Your gifts will make room for you.  The SEO Agency that hired me–told me they did so because of the potential I had demonstrated in the small wins I achieved for my clients. I had enough small wins to demonstrate to the Agency I understood marketing. However small time in my mind, it was enough for them.

They told me, essentially, that they didn’t mind teaching me the SEO skills because they saw I had marketing ability, I was teachable, and had enthusiasm for the work.  SEO is a very valuable digital marketing skill to have, as a marketer.  And God, graciously, positioned me to be chosen to get paid to learn it.


Principles You Can Apply to Your Life

  • Find what you are good at and keep your eye on that ball. Stay in your lane.
  • Overthrow doubt and fears’ influence any moment they rise up to harass you.
    • Find and learn techniques best suited for you. Prayer and Scripture are my technique. Proverbs and Psalms provide swords and gems to fight back.
  • Don’t let the pace of others, around you, distract or discourage you.
    • Celebrate them as they cross their finish line but keep your eye on your lane.
  • You are the average of the five people you spend the most time around.
    • So, keep smart people around you and those you’re positive will celebrate your small wins and applaud when you cross your finish line.


“All the best things that happened to me happened after I was rejected. I knew the power of getting past no.” — Barbara Corcoran


Remember, age is as age does.  If you are in your 40s or older and one day realize you spent X amount on a degree (s) or X years in a career that does not fulfill or match your best skills, then don’t be afraid to leave it–prepared or unprepared.

And if you try something new and realize–oh wait, I was on the right path, in the first place.  Then go back and pick up where you left off.  It’s okay.

This is life. It’s messy.  It’s unpredictable.  It’s an expedition.  Your lines don’t always have to be straight.  No matter your age–if you are breathing you can begin again.  If you make a mistake, just pause press RESET and start over.  That is okay.

And when your self-doubt manifests in imposter syndrome, shut it up!

Finally, I leave you with a video that illustrates, perfectly, the mindset, strategy, and heart behind all I confessed.  It’s a real race between a tortoise and a hare.  Please notice what the hare does…be the tortoise.


What about you?  What’s your story? Was this helpful? Did anything resonate with you?  If so, then please share it and let me know in the comments, on social (@goodbyebrokegirl), or email me your thoughts at Thanks for reading and sharing!

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