We caught up with Jonny Bobgan of Seekfire Creative and good friend of founder, Jared Kohn. Jonny shares with us his experience transitioning from full time employment to freelance work and being a business owner – along with the real life struggles and benefits.

Over to Jonny…


In January of 2017, I found myself out of a job. As the senior graphic designer at a small agency, I had been a loyal employee for five years. With the company going under without my knowledge, the paychecks began coming in late, and then not at all. I made the mistake of hanging in there too long, confident I wouldn’t be left hanging by my employers, who had become like family to me.

To further complicate our situation, my wife and I had recently taken custody of my teen brother and sister when we already had two kids of our own. Needless to say, this put extra pressure on me to maintain an income stream during these unexpected times. When it became obvious that I would no longer be paid for the hours I was working, I left the agency behind in pursuit of a new opportunity.

The Search for New Opportunities

I began my search with confidence, having received high praise from my employers, coworkers, and clients over the years. I had a diverse portfolio that showed my versatility as a skilled and experienced designer and illustrator. While at the agency, I had the opportunity to do a wide breadth of work from brand strategy and identity, to packaging and web design, and even some retail design.

As a leader, I had directed multiple simultaneous projects, established standards for quality control, and provided ongoing training and professional development to enhance team effectiveness and project workflow. As a solo designer, I had been responsible for the entire scope of large projects, from research, ideation and concepting, to the execution of design and artwork. My versatility, organization, and ability to operate efficiently under pressure had made me a valuable asset to the agency and the success of our clients. Certainly, there must be opportunities all over Seattle for someone like me.

The Disappointment

I soon discovered I didn’t fit the mold of the positions that were out there, or they just didn’t align with my needs. For the most part, they were either specifically for a specialist, too low of pay, or too far to be worth the commute. The few positions that I had real interest in didn’t seem to have much interest in me—I failed to even lock down any interviews. I would be lying if I said it didn’t damage my confidence.

All of the recruiters and hiring managers seemed to be looking for a unicorn. But I eventually realized that I was too. I wanted to keep doing all the types of creative work I had been so fortunate to do, and I refused to lose 15–20 hours every week to a commute.

My Transition to Freelance

Humbled by the fruitless search—and afraid of the looming debt with a family to provide for—I locked down some freelance projects to keep a bit of income rolling in as I searched for a long-term solution.

I kept busy creating the brand identity and website for a cool startup, overhauling the website for a Seattle construction company, and designing an interactive site for a local board sports company. I also had the amazing opportunity to put more time into my outdoor-inspired artwork, which I share to Instagram as @drawntosketching.


Soon enough, I realized I was far better at finding clients than finding a job. And in my mind, if nobody would hire me, I would show everyone—including myself—that I can making a living doing what I love without fitting the mold of job descriptions. Determined to make this work and fueled by the encouragement of my amazing family, friends, and past coworkers, I put my full efforts into freelancing.

The Epiphany

Despite the rollercoaster of workload consistency over the last year, I have a renewed passion for my work. I get to tackle challenging and rewarding projects for clients that I sincerely respect and enjoy working with. I am fully responsible for my work and the majority of my business development is from word-of-mouth from my supportive friends and clients.

I work far less hours than I used to and eliminated my commute, which has allowed me to spend more time with my children than most working dads get to. Being a morning person, I get to start work at around 6am and I’m rarely working past 3pm.

What presented itself as a crisis in the middle of already turbulent times turned out to be a blessing in disguise. Though I had considered the benefits of full-time freelancing in the past, I don’t believe I would have intentionally abandoned a secure job to try to make it work.

Moving Forward

I wouldn’t tell everyone they should dive into freelance work for financial prosperity and freedom. It’s never without uncertainties, and certainly not for the faint of heart. However, I believe if I can manage to support a family of 6 during this wild transition, anyone without kids—or at least professionals with more savings to fall back on—should give it a test run if they are tempted by the benefits. Without exploring the option, they might be missing out on one of the greatest opportunities for professional and personal freedom.

I look forward to continuing to grow as a designer doing work I love for clients I respect. I’ve learned a lot about business development and management over the last year. I continue to evolve my processes and integrate new tools to be even more efficient in my work, which I hope to share in an upcoming article.

Website: https://seekfirecreative.com/

Written by: Jared Kohn

Here at The Great Break we’re fascinated by reinvention – how people reinvent themselves to create new and exciting lives – morph their (new) careers around their passions. After all that is very much how and where this platform was first born.

Bryan Teare is not only a relevant case study then, but for those itching to make a change, a great coach and motivator. On the other end of the scale, the guy who went from top student to successful engineer and then morphed into a fitness trainer and now life coach (all thanks to CrossFit – read more of his story here), is solidly grounded and provides good insights for those who shouldn’t make a change.

In the first of a series of articles on life evolutions, we quizzed Bryan on the first steps to take if you’re looking to reinvent yourself.

1. Don’t just quit

Don’t just quit – don’t just jump ship like I did – without another option. It sounds sexy and it looks cool on social media, but really it creates a lot of stress. So what I would advise – if you are in a job you don’t really enjoy – see that as a blessing, you now have no pressure on yourself to start your own thing. Look at your current employer as an investor in your side business, because if you jump ship and start from nothing, and suddenly that first month hits where there is no income and you have to basically hustle to make things happen things can get stressful.

Whereas when you are in your (current) job you can spend one hour, two, three before or after work and work on your own thing. That way you get it up to a point where it is making income, before you just quit.

2. Focus

I mentioned the hours per day, or week (or whatever you have) to put in. What that limited time does is push you to really focus on the most important thing(s) in your new venture.

Here is fun exercise to do: Ask yourself, ‘if I had only two hours to spend a week on my business, what would sort of be the 80/20 of activities to do in that time?’ Suddenly things like updating your website or posting on social media, become a lot less important, whereas creating something that people would pay money for, becomes the biggest thing.

3. Make more time

Once you’re a little way along putting in the time on your new venture, take it a step further and put in some leave. Take a week’s leave from your current employer (if you have that much left over) and rather than just spending it on going somewhere or wasting that time, do an experiment… Look at what your life would be – what it would feel and look like – if you were doing your own thing.

So wake-up at whatever time you would do if you were working for yourself, maybe for you that is 7am instead of 6, or whatever. Make your breakfast and do your morning routine, go to a coffee shop or co-working space and take your laptop and do something that would contribute to your own business during this week.

Basically test what it would be like to work for yourself and on your own time. See if it is something you enjoy and, if not, then maybe the self-employed route is not for you. And, that is totally okay.

*Next installment: Finding the ‘sweet spot’ – should everyone be pursuing their passion as a career?

Website: www.bryanteare.com

Written by: Bryan Teare


Have a few questions? Chat with the team on WhatsApp or if we are out of reach send us an email to jared@thegreatbreak.com

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