I used to have a full-time job with benefits with a very prestigious university. I later quit to pursue my own freelance business.
However, it wasn’t so cut and dry.
There were (and still are) a lot of layers to pursuing a dream of working for myself.
The process I went through looks a lot more realistic (and doable) than some of the mythical stories you hear these days about making the jump from working for a boss to becoming your own boss.
This process can also spark some ideas for you to realistically take the risk too.
It may even help ease some of your fears and concerns preventing you from taking the leap. Here’s my story that began about 10 years ago.
Don’t Quit Your Day Job
For the first time in my career as a college career adviser, my creativity was being stifled under new leadership. I was also experiencing a lot of micromanagement under this new leadership.
I couldn’t continue to work under both conditions and had to start planning an exit strategy.
At first, this strategy wasn’t to quit my day job.
I started where most people start, looking for another job working for someone else doing the same thing elsewhere. Of course I wouldn’t leave my current job until I found my next job.
But, I never found the right fit.
Instead, I found opportunities that only served as an escape from my current situation. Not opportunities I could truly thrive in.
Are you just running to something that could possibly be worse than your current day job?
Don’t Quit Your Daydream
Next, I started listening to what my friends were telling me.
They kept telling me I would be good at wardrobe styling. This was something I’d been daydreaming about for a long time. Wardrobe styling would definitely provide a creative outlet for me.
But I still wanted to use the skills I’d developed as a career adviser over the previous eight to ten years. Those skills included interview coaching.
After giving it much thought and doing some research, I decided to start branding myself as an image consultant since image isn’t just about how you dress, but also how you present yourself in an interview.
Specifically, I branded myself as an image consultant for up-and-coming recording artists here in Nashville. I knew there were a lot of young artists moving to town and taking the risk to pursue music.
I also knew they lacked the ability to properly present themselves to a label (which is basically a job interview) or in a media interview (I’d had some past experience in media coaching too).
I went and got a business license. This is when it became real for me. But I still didn’t quit my day job. Not yet anyway.
Is there something people tell you you’re good at? Is it something you enjoy? Do you see a potential market for it?
Making the Shift to Starting Your Own Business
I worked on my branding efforts part-time while still working my day job as a career adviser.
Following my own advice to my students, I also spent my spare hours networking with the few contacts I had in the music industry and growing my network.
I attended as many industry events as I could and conducted informational interviews with several people in the music business, always asking for the names of two or three other people I should talk to.
For nine months I did this and my efforts began to pay off.
I slowly began getting clients. I worked with those few clients on weekends, evenings, and any time I had off from my full-time job.
Then, one of my networking contacts approached me about a part-time temporary job at his small music label.
This opportunity reduced some of the risk and gave me a bit of a safety net to leave my full-time job and pursue my business full-time. (This is just one example of why networking is so important!)
However, I still wasn’t hasty in my exit from my day job.
Instead of giving two weeks’ notice, I gave 30 days’ notice because the policy was I could work for the university again in the future if I gave 30 days’ notice. But not if I’d only given two weeks’ notice.
I wanted to keep as many options open in case things didn’t work out.
I used the three months for the temp job to increase my networking efforts in the music industry and promote myself to potential clients. This way I would have more lined up once the contract was up.
What are some small steps you can start taking toward your daydream? Are they things you can do around your day job? Who are some people you can start meeting and connecting with? Can you come up with some ideas for an eventual exit strategy from your day job? Do you have a potential safety net you hadn’t previously thought of?
Don’t Let Fear Overwhelm You
Once I was on my own, I was already getting used to working for myself and there wasn’t as much to fear as I would if I’d left my day job and then started a business.
This isn’t to say I had no fear at all. A few days before giving my notice at my day job, I experienced my first (and luckily my only) panic attack.
Then, when the economy tanked in October 2008, less than two months after I’d left my day job, I started to get nervous.
But, what I saw happening all around me was people being laid off and being forced into becoming their own boss with no real planning or preparation.
Luckily I was way ahead in that department because I’d already been preparing for nearly a year. And I already had some clients.
When I was short on image consulting clients, I supplemented my work with resume writing and career coaching services for those who’d been laid off during the recession and were looking for a new job.
Are you still having some fears about pursuing your daydream? Are these fears real or perceived? What are some ways you can calm your fears or put them into a different perspective? What would be the worst case scenario if those fears proved true? What’s the best case scenario?
Click here to read more about the myths of the common fears of leaving your job.
Rely on Connections to Supplement Your Income
Throughout my time as an image consultant I continually made connections through networking which turned into additional ways to supplement my income with my growing business.
While attending a fashion show, I met the president of a small design college who hired me to teach a class on image at the college for a semester.
He also ended up publishing the 2nd edition of my first bestselling book, Advance Your Image, through the school’s small publishing company.
While attending an event at the Entrepreneur Center here in Nashville, I met someone who needed a contract employee with career advising experience to do outplacement counseling for his clients.
I still do this work to this day because I get to make my own schedule and it’s the complete opposite of micromanaged work. I love it.
The connections I’d made through my original day job also led to a part-time (10 hours/week) temporary job at another university, which unexpectedly turned into a part-time permanent position.
I was hired to fill in for one semester while one of their employees was on maternity leave. But when she returned, they asked if I could stay on indefinitely. I got to make my own schedule so I could work it around my business.
Eventually they asked if I could work 20 hours a week. As much as I loved working at this university, I’d already put in so much blood, sweat and tears into my image consulting business that I couldn’t afford to risk that much time away from it to work for someone else.
So I decided to be fair to both myself and the university and leave so they could find someone who was able to give them the number of hours they needed.
Are there connections you have now in your current situation which could benefit you in the future? Are there connections you’d like to start making? What are some things you can fall back on to reduce financial risk when your daydream business is slow?
Be Willing to Shift Gears When Necessary
After leaving that part-time job, I realized I was burned out on seven years of image consulting and wanted to do something different.
But what? I had no idea.
I just knew I didn’t want to risk all the work I’d put into developing my brand.
Then a year and a half later I realized I still wanted to do career advising, but this time on my terms. (Click here for the story on how this realization came about.)
I still wanted to be my own boss. And I wanted to keep the same name from my image consulting business.
I was able to do both with a slight shift in my mission and an overhaul of my services.
Now, I offer unique career coaching services focusing on helping people discover and pursue their own passions.
This includes helping them either find a new day job they’ve been daydreaming about, or helping them take the steps (not the leap) to becoming an independent freelancer or business owner. Whichever they’re most passionate about.
My business became more successful once I was willing to make this change.
I was also able to see how the experience I gained and the tools I developed in my image consulting business fit nicely with my new mission and offerings.
Today, I don’t have to supplement my income anymore.
Now, I get to do it simply for the love of the variety in my schedule and the love of the creativity it brings me.
Unfortunately my time only lets me do one additional gig to my full-time daydream.
But I’ve never been happier in my work.
No one is micromanaging me or stifling my creativity.
I get to choose who I take on as clients and which projects I want to invest my free time into.
How can I start planning my exit strategy for my day job and my entry strategy to my daydream? How can I reduce unnecessary risk? How can I maneuver around inevitable risk?
How I Did It
I simply started setting goals and then taking small steps toward achieving those goals.
You may want to pursue your daydream of starting your own business but think it’s impossible.
And it may be impossible for you if you simply quit your day job to follow your daydream.
I want to serve as one of several examples of how doing it with an alternative, less-risky strategy can make it possible even for you.
Probably more so than you ever imagined.
Biggest Lessons Learned
Want to know the biggest lessons I’ve learned in the past 10 years working for myself as a freelancer (so you don’t have to learn them the hard way)?
Check out my post 10 Lessons I’ve Learned From 10 Years of Freelancing.
Click here for more resources and posts on the topic of working for yourself.