Leaving the corporate world to pursue a full-time career in music, I wasn't excited. I was anxious.
I've always been risk-averse, security-oriented, money-motivated… probably not quite the personality you’d imagine in an artist.
Though friends, family, and strangers admired my "courage," I felt uncertain of what my future held. No base salary? No healthcare? No compliance trainings?? (Okay, that one I could live without.)
Beyond the incessant self-doubt, I felt guilty. Had I wasted two and a half years in a corporate role? Would this pivot cause my professional skills to atrophy?
It didn't take long to realize: no.
The professional tools and skills I had previously learned weren't going anywhere. In fact, they would prove essential in becoming a successful full-time musician in the live music capital of the world.
Crossing the Threshold: Carried By Sales
Cue: my most significant phase of professional growth thus far. In leaving my 9-5, I became an overnight entrepreneur — a title I had never craved but soon realized is the true fate of a full-time performer. If music is your livelihood, then charging for it is part of the work. And at some point, passion needs an invoice.
So I started with what I knew, and I built a book of business. I prospected venues through cold call outreach. I networked with other professionals to build community, gain insight, and establish a positive reputation on the scene. I researched local performance agencies and pitched my way onto their competitive rosters.
It was a relief to realize I wasn't starting from scratch. My SunPower days had taught me pipeline management, consultative selling, and the discipline of consistent follow-up. It was corporate I could thank for my early, easy momentum.
And as the gigs started rolling in, I grew confident that maybe I could make this sing-song thing actually work!
Tests, Allies, and Trials: Client Relations and Co-Creation
I needed some new skills to address both the higher volume and wider variety of inquiries.
When I say variety, I mean variety: weddings, corporate conferences, jazz clubs, anniversary dinners, baby showers, graduation parties, nursing homes, brunches, music festivals, holiday parties, benefit shows, broker’s opens, and house concerts…
Each client possessed a unique vision with unique conditions. Nearly every booking meant rolling up to a new venue to collaborate with new planners and new vendors. I learned how to deliver a high-caliber performance, juggle logistics, and coordinate equipment/musicians all while responding to unfamiliar and constantly-changing variables.
Many of those clients were Fortune 500 corporations (JPMorgan, Honda, CVS Health, Zoho, Kohler, Wyndham, and others). In these cases, my professional corporate lingo got me pretty far - but I still had to navigate (then master) new territory like the procurement process, insurance minimums, and a whole host of other legal requirements.
Meanwhile, weddings and private events demanded all that and more — with an additional layer of heightened emotional sensitivity and meticulous attention to detail. Deceptively high-pressure work.
And there is no rest for the self-employed! Post-performance, I followed up with bookers and agencies to turn clients into referrals or repeat customers.
Six months in, I was spearheading client acquisition, vendor relations, contract negotiation, and event execution — all with zero oversight or assistance.
Seizing the Sword: From Self-Employed to Employer
I’ve always been a people-person, so I genuinely enjoyed working one on one with clients to understand their vision and generate excitement for their event. And as I received more and more requests for ensemble set-ups, I was happy to bring in a team in order to meet their requests.
To date, I've onboarded 25 musicians into my payroll system. This process included prospecting and screening candidates, training them on expectations, loading W9 information, drafting contracts outlining communication standards and conduct, and balancing multiple calendars to schedule rehearsals and book performances.
The most surprising part of this unexpected leadership? It was fun!! I was now responsible for curating team culture, keeping my band happy, assessing strengths and weaknesses of individual players to assign the right person for the job, managing expectations and setting standards for my team.
I had built something from nothing. I was solving problems under pressure. I was leading a team. Had I drunk the kool aid and become… an entrepreneur??
The Ordeal: Systems and Operations
It’s always right when you start to get confident that you can expect a humbling experience right around the corner. For me? It was bookkeeping and systems. duh duh duhhhhh
Word-of-mouth referrals were rapidly accruing, and the scale of my operations was exceeding my existing skillset and business processes.
Hiring band members → payroll
Billing clients → invoicing
Gear and other operating expenses→ budget
At first, my lack of experience in these new systems and bookkeeping yielded much slower results than customer acquisition. But through diligence and discipline, I established internal systems to make my business sustainable and scalable.
I taught myself QuickBooks, navigated insurance requirements, ensured tax compliance for a growing subcontractor network, and managed A/V rentals and travel logistics. I built my own marketing stack—Wix for my website, Canva and CapCut for creative assets, Meta Business Suite, TikTok Studio and Laylo for ad campaigns.
Now two years in, I've got a system that has allowed me to successfully execute/deliver over 300 bookings across 10+ cities and two states for household name clients.
Master of Two Worlds: The Transferability of the Entrepreneurial Spirit
Having worked in both a corporate setting and the arts, I've seen firsthand that many skills—team management, client relations, contract negotiation, operational discipline—are valuable in any professional setting. What did I learn? I was already more equipped than I thought. Seemingly unrelated experiences combine to prepare you for opportunities uniquely suited to you.
Whether you're wanting to start your own business or apply to someone else’s—do it. You’re likely much more qualified than you’re giving yourself credit for. And if you aren’t? You’ll figure it out. That's the real secret: trusting that you can rise to the challenge. Adaptability, cleverness, and grit carried me through my limitations, and they will take you through yours. Take the leap, and maybe you’ll have a great blog post to write about it afterwards.
