The 6 Personal Development Stages That Took Me from Secretary to Self-Employed

One of the most incredible (unexpected) side effects of starting this blog and deciding to share my experiences with starting businesses, dealing with crushing defeats, and going through painful personal development stages, has been the revelation that I’m not alone in my failures.

And you know what? Neither are you. None of us are.

Through my blog, I’ve been able to meet tens of thousands of entrepreneurs who’ve struggled with everything from pulling themselves out of massive debt and deciding which type of business they should start now, all the way up to successful businesspeople who are looking for the next big growth lever that can take them from hundreds of thousands–to millions each year.

It’s been a hell of a learning experience for me.

Despite all of the differences between the people I’ve met here, one thing has always remained a constant: we all have challenges.

We all have to make difficult decisions on a regular basis. We all go through phases in our lives, when we’re really just not that sure of what we want to do (or be). And that doubt is normal. In fact, it’s something that even the world’s top entrepreneurs experience. It’s a natural phase that most of us experience, in our journey through life as we grow through conscious personal development.

Every once in a while, I’m fortunate enough to meet someone through my blog, who has such an amazing story to tell, that I am absolutely compelled to share with you.

Today, I want to share with you one such story, from someone who’s very quickly developed into a regular source of inspiration, motivation (even more than my favorite motivational quotes 😉), and friendship for me.

Her name is Caroline Beaton

Caroline writes about the psychology of millennials at work for Forbes, Psychology Today, The Huffington Post and many others. She also has an insightful weekly newsletter that I highly recommend, if you want to develop the research-backed habits you need to succeed. Head over and subscribe to her newsletter today, you won’t regret it.

Now, I’m going to turn it over to Caroline.

Here’s Caroline to share her incredible story of going from secretary to self-employed, by focusing on personal development to discover the work she truly loves to do.

Caroline Beaton on ryrob dot com

How I Failed, Recovered, and Built a Powerful Personal Brand, All Before Turning 25

It rained every day, and I had no idea what I wanted to do with my life.

I sat in my small apartment in Vancouver’s dark and wondered why I left home, why I graduated college and why I moved to Canada.

I tried writing about it:



The “real world”, I decided, was “a foggy living room without contacts.” “How did I get here???????????????” I wrote. I felt “doomed to uncertainty.”

Yes, a tad dramatic—especially considering I wasn’t ill, wasn’t in jail, wasn’t broke. I wasn’t even alone; I lived with my boyfriend.

The problem was my 9-5.

I was a secretary at a downtown law firm. I hated it, but I didn’t know what else to do or how to do it. I wanted to be Lululemon’s Senior Director of Marketing right out of college but, well, that didn’t work out.

So I ended up in the place I’ve since learned so many millennials land post-college: lost.

Two years later, I’m a millennial expert, an award-winning writer and a contributor to publications such as Forbes, Psychology Today and The Huffington Post.

I’m 100% self-employed, create my own schedule, and cherry-pick my priorities. I’m financially self-sufficient and I’m teaching others how to do it, too.

Like those lucky, laid-back coffee shop dwellers I envied in Vancouver, my office is now my laptop and my boss is me.

For anyone sitting at a job you hate, stuck between passions or writing nonsensically in ALL CAPS, this post details how I pulled myself out of my post-college funk and created a self-directed career of my dreams.

Though perhaps not quite as linear as they appear here, these are exactly the steps I took to change my career and my life. The images below, snapshots from the journals I’ve kept for the last two years, are evidence of my process:

1. I Became a Better Me.


“Your level of success will seldom exceed your level of personal development, because success is something you attract by the person you become.” – Jim Rohn

I never encountered that quote during my lost phase, but I did repeatedly discover its truth.

For the first four miserable months of my time in Vancouver, I feverishly applied for jobs and PhD programs, hoping something—anything, really—would rescue me from my present circumstance.

Nothing worked. I remember sitting in the park outside my apartment and consciously giving up. But once I abandoned my incessant pursuit of a better job—convinced that was my path to happiness—I was able to improve my wellbeing and subsequently my career.

I stopped applying to jobs for several months and instead threw myself into my surroundings and crafted each day with self-care. I started waking up an hour earlier to write; I walked alone regularly; I began a yoga teaching mentorship; I studied spiritual and self-help texts and listened to audiobooks.

I never skipped with joy in Vancouver, but I did get to a point where I fully accepted my present situation and took care of myself on a deep, holistic level. It’s cliché but, truly, self-development is the first step to reforming your career–at least it was for me.

2. I Remained Open to My Interests.


There are many ways to explore potential career paths without leaving your day job.

Through classes, research, podcasts or talking to people, I learned what careers in stone carving, massage therapy, naturopathy, academia, law and supply chain management looked like.

Sometimes I had to scamper around the city to make it to various events, but I never had to abandon my consistent source of income.

Throughout these experimentations, I sketched and, sometimes just subconsciously, imagined myself in each career. Though occasionally I felt overwhelmed with so many options, I tried to embrace all of them as exciting potentials. Because I didn’t put any pressure on myself to choose just yet, trying out different paths felt–almost–fun.

When you’re lost, it’s tempting to just pick a path and run with it—because admitting you don’t know where you’re going is horrifying.

But “route traveling”, what psychologists call blindly adhering to one path despite evidence it’s not working, is usually unhelpful. Instead, the first task of any successful creative, according to psychologist Mihaly Csikszentmihalyi, is backing up and noticing what’s interesting or exciting to you. Don’t assume you will or won’t like it; let your experience be the evidence for your direction.

The most critical part of both self-development and staying open is not having an external agenda. Slow down. Thoroughly get to know yourself and what you love. This self-awareness will prevent you from rushing through and winding up burned out or full of regret.

3. I Prioritized and Integrated My Passions.


After taking several months to look inward and truly acknowledge what excited me, I began to narrow in on my passions.

I asked myself, “What’s the work I can’t not do?” Then I tried to eliminate everything else.

As it turned out, there was quite a lot I couldn’t not do, including art, writing, psychology and self-development. Still, crossing off law, international travel, English literature, teaching yoga and many others was incredibly freeing. When you purposefully shut doors, your career begins to feel cozy, hopeful. You start to remember what matters.

If you feel like you’ve been open with yourself for long enough to know everything that’s possible for your career, try this exercise right now.

Write a list under the heading: “If I don’t do this in my [twenties, thirties, etc.], I will regret it.” Answer with the activities you couldn’t live without. Kill the rest by deciding to permanently not pursue them—at least professionally. Celebrate.

Then, I had to decide how to balance my seemingly disparate passions. So I created a flow chart (the image above). As I continually engaged all five of these interests, I realized how much overlap they actually had. I began noticing and even creating commonalities. I was committed to their intersection. Now I could niche down.

4. I Focused.


Here’s the weird thing about choosing to pursue all your prevailing passions simultaneously: their unique permutation creates a speciality.

So, even if you feel like your interests are way too broad and could never yield just one profession, combining them can create a path no one’s traversed before. You may have doubted my flow chart above (I did), but I’m currently putting every one of those passions to work in my personal brand and business.

I’m able to do this now thanks to one technique: starting a side business! (Ryan’s side business of choice was to start a freelance business)

For the last two years without pause, I’ve side hustled at one thing while holding a full or part-time job, at all times.

This is exactly what I did:

  • Full-time job: Secretary. Side business: Marketing Intern at Bhakti Chai.
  • Full-time job: Marketing Coordinator at Bhakti Chai. Side business: Elephant Journal editorial apprentice.
  • Full-time job: Elephant Journal editor. Side business: freelance writing and freelance content marketing & copywriting.
  • Full-time job: writing and my personal brand. Side business: freelance content marketing and brand strategy.

Having a side business is hard and time consuming, but it has never failed me. Note, however, that my side businesses have changed dramatically over time.

It’s okay not to have The Grand Plan perfectly mapped out. Your interests will change as you grow and learn, and your priorities may shift over time.

But this doesn’t mean you can’t choose a profitable niche for your side business. In fact, Ryan built a free online business course to help you validate your business idea and start getting your first paying customers. It’s called, Finding a Profitable Business Idea.

In fact, you should niche down to figure out if that particular combination is a viable path. If it’s not, you can pivot with the confidence that you’ll still have an income.

5. I Did it Anyway.


Of all the logistical challenges of taking charge of our careers, our own minds hold us back the most.

Here are three internal setbacks – the personal development hurdles – that I faced along the path to discovering my self-employed dream career.

Challenge #1: Acknowledging That I Failed.

I never understood the hype about failure until I failed.

I failed at landing my dream job—or really any good job—post college; I failed to get accepted to an English Literature PhD program; I failed at my seven-year relationship. But failure can be—and was for me—an excellent director.

J.K. Rowling explains in her Harvard commencement speech that failure has “fringe benefits.” Indeed, being lost post-college was the foundation for my current career; I don’t even like reading English classics; My long-term boyfriend wasn’t the right guy for me, and failing helped me find one who is. If I’d known I would have failed at these things, I probably wouldn’t have tried as hard, if at all, nor learned as much about myself and my purpose.

Challenge #2: Seeing That Other People Doubted Me.

As I strategized about how to leave my editorial position at Elephant Journal and traditional employment, my mom and boyfriend—two people I trust more than anyone—told me I should set more realistic goals. They both encouraged me to remain employed, if not at Elephant then elsewhere.

It was, of all people, my then-boss who told me, “If you’re still at Elephant because you think you can’t make it on your own as a writer, you’re wrong, and that’s the wrong reason to be here.”

Challenge #3: Recognizing That I Doubted Myself.

Oddly, I never doubted myself until I actually followed through on my dream of self-employment. Now I doubt myself practically every day.

I think, “I can’t pull this off. What is ‘this’ even? What am I doing? I don’t even know what I’m doing and I expect people to pay me for it?” Even as I wrote this blog, I asked myself, “Is my story really worth 2000 words?”

Through failure, criticism and self-doubt, I did it—and continue to do it—anyway.

When I’m feeling bad, I play out the worst-case scenario. Maybe today’s worst case is: “No, you’re not worth even a word, and you’re going to die poor and alone.” Well, that sucks, but if it’s going to happen either way, I might as well tell people how I got as far as I did.

Doing it anyway often requires looking outside yourself and asking on a larger scale, “How can I help others?” Then, it’s not about you or your personal failures; you have nothing to lose and everyone else has everything to gain.

6. I Mastered it.


Does this sound familiar?

“I’m not where I want to be yet, but I don’t want to be miserable until I get there, because I’m smart enough to know that when I get there my dreams are going to get bigger, so I’m setting myself up for a life of misery.”Marie Forleo on her early twenties.

This drive is called ambition—and, if you’re reading this article, you probably have it.

To make ends meet while she pursued life coaching as a side business for seven years, Marie was simultaneously a bartender, personal assistant and dance coach. The mentality that saved her from perpetual misery was: “Whatever is happening in this moment, I’m going to approach it and attack it—whether I’m bartending or scrubbing someone’s floor.”

Even having “made it”—at least according to my flow chart—I constantly strive for more. When I’m discontent, I’m tempted to detach. In fact, a deepened commitment and acceptance of my situation is in order.

Of course, wanting to be and do better is okay, but not if it comes at the expense of your well-being. If “be present” feels too cliché, reframe your current action plan in terms of current mastery.

“You have to train yourself,” Marie says. “I’m going to master this, I’m going to bring my A-game, I’m meant to be here, this is my party.”

Never sacrifice what you’re doing right now to a future dream. What you’re doing right now becomes your future dream—but only if you do it well.


Personal development, harnessing my passions, focus, perseverance and present mastery are the basic ingredients of my business and my success. But it didn’t happen overnight. And, though I’ve come a long way, I’m not exactly yoda (or Marie Forleo) yet.

But I do know a few things about living your dream before you’re too old to enjoy it, and I learn more every day.

If you’re ready to own your career—whether that means freelancing, entrepreneurship, promotion, or switching jobs—sign up for my newsletter to receive my latest insights.


Written by Caroline Beaton

Caroline Beaton writes about the psychology of millennials at work for Forbes, Psychology Today, The Huffington Post and many others. Subscribe to her newsletter to develop the research-backed habits you need to succeed.

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58 replies to “The 6 Personal Development Stages That Took Me from Secretary to Self-Employed”

  1. Since I was a little girl I always wanted to write. I have my Bachelors of Science degree in business. I graduated in 2015, Since college I have taken a break as you can say, Doing something else in my own time seems impossible, serving others where I am needed to help others make progress. An added light to the dark side as one could say. I have since last year was a caregiver for my father who died at home from cancer. It will take much time for me to get over and now I am here to help mother and myself through these rough times. I have since January am taking a course to find my niche and be a writer myself. In these times of grieving I found that finding a distraction to occupy oneself helps me grow as a person and is a way of light into a new chapter in my life. A new beginning to an end.

    I was wondering what kinds of writing do you and Forbes use and who I can contact for writing position with you or Forbes. I can write in several areas but my niche is going to be in self help and self Development to help me heal.

    Thank you for your time and your help.