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. Yes! Love this so much, and totally agree that it’s the INNER work that’s going to help you succeed.

    • Diana, thank you! Agreed: I could talk about logistical steps all day long but, for me, the details wouldn’t have fallen into place until the fundamentals did. Best of luck to you!

  2. Bi Caroline,

    Thanks for sharing your thoughts. They are very common, because I can agree with lots of them! Kudos to you on your success and keep going!


  3. Inspiring.

    After many rejections in the job market, I am compelled to draw on what I believe my innate Strenght: Imagination, writing, inventiveness and the nascent entrepreneurial drive.

    • Noel, yes! I just gave the below advice to someone actually–sounds like your aim 🙂

      Sit down and decide how you’re going to share your light with the world. Forget precedent and expectation. Where will YOU come through? Go there, do that!

      Good luck!

  4. Thank you for sharing your story! It is great!

    I’m in mid-20s, and I have been having the exact same struggles after college.
    I have wanted to be where I feel right, but I couldn’t figure out how to reach that place.

    I remembered that Steve Jobs once said “Don’t settle.” in his famous speech, and you did exactly that and found what you love to do.

    This article is so helpful and inspiring to me and I’m thankful so much to you.

    Greeting from Japan.

    • Akihiro–Thank you so much for commenting! I’ve since heard lots of similar stories to mine (if only I’d known I wasn’t so alone at the time!). Take care of yourself–one day at a time.

  5. Great article!

    I also ended up lost after graduating and landed a corporate IT job with my art degree. I thought having stable income would make me happy, but once I started to feel miserable a few months in began the journey of inner work that’s led me to start my first business 8 months later.

    Your story is inspiring and parallels the steps I’ve been through in a lot of ways, and at 24 now, I hope I’m standing on my own feet without a job by the time I hit 25.

    • John,

      Wow, congrats! Stable incomes are so tempting. In fact, sometimes I miss them! But I’m glad you’re not kicking the can down the road as so many twenty-somethings do who later wind up with regret. Keep at it, and good luck taking the leap!

  6. Wow, what a tremendous article. I am 52 coming on 53 but still think I am 25 and act it too, kind of. I really don’t think that anyone is to old to pursue their passions because this day many older workers are doing this because they are, will broke. I continue to learn each day from articles like this on and am now on a similar journey. I always have known that I should be my own boss and working for someone else poisons me a little bit each day. Sure, like you, I am taking on different types of work and continually to work on me and my business. From a x’er, thanks.

    • David, I totally agree! Sometimes people comment on my other articles with “but this isn’t just a millennial problem”–and they’re right! We’re all human. I just write about what I know, and I happen to be a millennial ;). Regardless, I’m so happy this piece resonated with you. I hope Ryan’s blogs/courses on side hustling can help you become your own boss someday, because it sounds like you were made for it!

  7. Thank you for sharing! It sounds like I’m going through a very similar “lost” phase as you did so your article is extremely relevant. I’ve already embarked on a version of your #1 and am somewhere in #2. I loved the flow chart idea to find the intersection of your interests that’s unique to you and will definitely be working on one for myself.

    • Thanks for reading, Melanie! #2, remaining open, was one of the hardest ones for me because by nature I’m a starter; I’m impatient. But really taking the time to get to know yourself is unbelievably helpful in the long run. I hope you grant yourself the time to enjoy that journey because it really is worthwhile. Good luck, and I hope you stay in touch with me however you choose!

  8. I want to thank all the circumstances that lead me to read your article. While reading it felt, I was having a conversation with my alter ego. Could relate to all the challenges, fears and anxiety. I’m awed by the way you have dissected this complex struggle.

    Is there a specific routine you follow to come up with solutions for self development?

    • Simran, I really appreciate your words and I’m glad they were helpful 🙂

      I often think of self-development more in terms of “rituals” than “routine”, which can feel a little rigid to me. So rituals include my sketchbook; drinking tea/lighting candles and thinking, planning out my strategy; spending time outside; going on walks; I’m a huge scheduler–I’ve found that the most successful people write their goals in terms of dates not just to-dos. For the past several months I’ve also been waking up an hour earlier to think big strategy on my business, draw, read and take time for myself that otherwise tends to get forgotten during the rest of the day. Another monumental self-development practice for me is yoga. Setting an intention, however you choose to do it, can really be a fruitful practice. Good luck, and keep me and Ryan posted!

  9. Glad to see a hard work by Caroline, I also do the same but unfortunately , no work is smooth now a days so am waiting n passing time to study n gain much ability in software language with believe that one day will be of mine .

  10. Wow, you really don’t know how your story inspired me as among the people struggling with the job I think am not suppose to be doing… I want to quit but everybody else is telling me not and at the end I get scared and continue to stay. I really wanna have my own sales training company but am damn scared to dare.. Your story has just helped me to re plan my plans and am now Inspired and have courage,

    • Benter, so happy to hear it! I don’t know everything about your situation, but at first glance I’d recommend building up your company on the side and essentially testing it out while you still have income. Just make sure you’re not doing side work on the job, violating non-competes etc.. In my mind you’ll need to prioritize a) your company or b) improving your current situation immediately. If you really do hate your job, you won’t have the energy to do something on the side, so I might recommend slowing down your longterm plan, finding a job you like more and then building up your side business. Whatever you do, keep us updated and good luck!

  11. Thank you so much for the article, you have no idea what you just did for me. This has been and is my current struggle. I feel so inspired. I feel like this article was written for me. Thank you so much and wish you all the success that you desire.

    • Samukelisiwe–I’m so glad you found it helpful! And thanks for commenting and letting me know. You have it in you to make great things happen. It’s just a matter of strategy and tools!

  12. Caroline, this was an incredible post. I’ll certainly be sharing it with my likeminded friends. I’ve had this page opened in a tab on my IPad for months now. Something about the introduction wouldn’t allow me to close it without reading, yet my biggest weakness (procrastination and not fully handling certain tasks all the way through, one at a time) prevented me from doing so. Upon graduating from college, I started a business I had dreamed about starting for years. I’m just over a year in, and have learned so much about the industry, how the real world works, and myself. Similar to you, there are too many things in life that I am passionate about to eliminate some for the benefit of the others. Ever since my junior year in college, I became really into self improvement. I loved reading your resolutions chart, because I have started doing a number of those that weren’t so natural to me as well (writing everyday, reading/learning everyday). The self discipline aspect and holding myself accountable has been the toughest part, but reading about your journey and the correlations between the two journeys makes me feel reassured, for whatever reason. I can’t complain with where I am. I’m very actively living out/seeing progress with early phases of three of my biggest passions and goals (my business, coaching basketball, my relationship/building a dynamic family), but my true goal is to live out EVERY passion and dream that makes me tick, on a daily basis. Reading this article has me motivated to do so and to organize my life even more to make that possible, as it appears you did. I have long been interested in blogging, but as you mention above, my passions are all so unrelated to each other through most people’s eyes. As an entrepreneur, sometimes I feel it’s best that I keep my opinions to myself, my friends and those that I mentor, so as not to affect my business. I also feel the same in regards to being a basketball coach. For instance, I’m very passionate about the health benefits behind cannabis and how the plant can save countless athletes from becoming dependent on pain killers and the ensuing depression. This being said, I currently reside in the south, where cannabis is still illegal (not to mention tested for at every level), frowned upon and overall misconceived. That was just an example of an inner confliction I have when thinking about blogging. I have recently begun writing a book that I have wanted to write since graduating, and am hoping this will provide an outlet for organized thoughts and opinions I have relative to the story, while not sharing with the public until I manage to finish, which certainly won’t be anytime soon. I have subscribed to your weekly email, which makes you one of three subscriptions (Shopify and Pocket) I have coming in. Looking forward to more literatureal gold from you.

    • Trey! Oh my goodness this was such a fun, inspiring reply to read! It sounds like you hardly needed my post to be honest, but I’m glad you found it helpful. It seems like you’re on the right track. I know how hard it can be to distill everything you care about into a daily direction. Looking forward to keeping in touch with you on my newsletter — take care!

  13. Typically I do not read content about blogs and forums, on the other hand want to state that that write-up very compelled me to undertake and so! The publishing flavor have been surprised everyone.. click this link now Many thanks, very nice submit.

  14. I absolutely loved this Caroline! I left a full-time job to strike out my own two years ago when I had my first child. I figured I’m already scared out of mind with the responsibility of raising a human being, failing in the working world would be small potatoes. Like you, I had small failures, but overall have been successful. It’s amazing what you can do when you believe in you.

    • Erin,

      That makes me so excited and happy to hear! Life is too short to be scared. Of course we should assess risk, but it sounds like the timing was right for you. Take care!


  15. Awesome. I love this! Continue with your awesome work.. This is very inspirational and informative.

  16. I think what you said made a great deal of sense. But, what about this?

    suppose you added a little information? I am not suggesting
    your information isn’t good, but what if you added something that
    makes people desire more? I mean 6 Personal Development Stages I Used to Start a Business is a little boring.
    You could look at Yahoo’s front page and note how they create post titles to get people to
    open the links. You might try adding a video or a related picture
    or two to grab readers interested about what you’ve got to
    say. Just my opinion, it could make your posts a little livelier.

  17. Thank you for such a meaningful article. It is really going to help me and everyone, who are reading the article to another level.

  18. Hi Caroline,
    Not sure how I even came across this, but it was a very insightful read, especially at this stage in my life. While I am well into my 40s, I can’t help but feel lost. I feel as if there should be a greater purpose to my life. I feel as though I am not living up to my full potential, although I have no idea what it is I’m supposed to be doing! It’s a frustrating place to be. I’m seeking more avenues of personal development to help understand myself on a deeper level. I only hope it doesn’t take me years to live and succeed at my full potential. If there are any audio books you could recommend, I would greatly appreciate it.
    Much success to you in your future.

  19. Thanks for the share Caroline, inspiring stuff. Its been some time since you wrote it, I trust the journey has only gotten better! Congrats and all the best for the future