A lot of people assume they are starting over when they enter the online business world.
They think:
“I don’t have the right background.”
“I’ve been out of the workforce too long.”
“I need more experience before I can do this.”
But this episode of The OBM Show challenges that idea completely.
Because before Jessica Bonilla ever called herself an Online Business Manager…
She was already operating like one.
Click here or on the preview below to watch now:
Prefer to listen? This episode is also available as a podcast on the OBM Show Podcast here.
The Skills Were Already There
Before becoming an OBM, Jessica worked as an executive assistant inside a corporate IT department supporting executives, managing moving parts across teams, and learning how operations functioned behind the scenes.
At one point, she was the breadwinner in her family.
Then life shifted.
After losing childcare, she stayed home with her children, eventually homeschooling them while continuing to volunteer, go back to college, support her husband’s construction business, and take on different jobs along the way.
But like many women who step away from traditional career paths, Jessica slowly started believing she needed to “start over.”
What became clear throughout this conversation is that she was never starting from zero.
She already knew how to:
- manage complexity
- adapt quickly
- communicate with different personalities
- identify breakdowns
- solve problems
- keep moving parts organized
- think operationally
She just had not connected those skills to the OBM role yet.
The Transferable Skills Most People Overlook
One of the most important themes in this episode is how much people underestimate transferable skills.
Jessica talks openly about how homeschooling strengthened her ability to read people, recognize gaps, adapt systems, and understand how different individuals operate best.
And honestly… those are core operational leadership skills.
Because being a great OBM is not just about managing tasks or learning software.
It is about:
- recognizing patterns
- understanding pressure points
- helping businesses adapt
- communicating clearly
- leading people through change
This is why some of the best OBMs often come from backgrounds like:
- executive assistance
- teaching
- project coordination
- corporate support roles
- customer service
- management
- caregiving
- or even simply years of managing households and complex family logistics
The skills are often already there.
They just need to be translated into the online business world.
Why Confidence Matters More Than Knowing Every Tool
Another powerful part of this conversation is Jessica’s honesty around confidence.
Like many new OBMs, she initially questioned whether she was qualified enough.
But what helped her build momentum was not knowing every platform or system perfectly.
It was:
- curiosity
- consistency
- visibility
- operational thinking
- and trusting that she could figure things out
She shares how consistently posting online and speaking directly to founder pain points helped her land her first clients.
Not by going viral.
Not by having a massive audience.
But by helping potential clients feel understood.
This is such an important reminder for aspiring OBMs:
Clients are not looking for perfection.
They are looking for leadership, problem-solving, and support.
Emotional Intelligence vs Operational Intelligence
One of the most insightful parts of the episode is Jessica’s perspective on emotional intelligence and operational intelligence.
Because operations work is not just systems.
It is people.
It is understanding:
- why founders resist delegation
- why bottlenecks happen
- why team communication breaks down
- why overwhelm impacts decision-making
- and how operational structure affects leadership capacity
Jessica explains that operational intelligence is often about identifying the gaps and solving the problems.
But emotional intelligence is what allows you to navigate the humans inside those systems.
And honestly?
That combination is what makes a truly exceptional OBM.
“Pivoting Does Not Equal Failure”
One of my favorite moments in the episode is when Jessica says:
“Pivoting does not equal failure.”
And I think that message matters deeply for anyone rebuilding, reinventing, or stepping into something new.
Because careers evolve.
Businesses evolve.
Life evolves.
Sometimes the path is not linear.
But that does not mean your past experience loses value.
Often, it becomes the exact thing that makes you uniquely qualified for the next chapter.
The Next Step
If you’ve been thinking about becoming an Online Business Manager but questioning whether your background “counts” enough… this episode is your reminder that operational leadership often starts long before the title does.
You do not need a perfect entrepreneurial story to become an OBM.
But if you do want support, the OBM Accelerator is the best place to start.
Inside the OBM Accelerator, you’ll learn how to position yourself as a strategic operational partner, build confidence in your skillset, and create an OBM business aligned with the kind of clients and work you actually want.
For business owners reading this and thinking, this is exactly what my business is missing…
You do not need to keep holding everything together on your own.
You can explore our Directory of Accredited OBMs or be matched directly with the right partner through OBM School’s matchmaking process.
It’s time to SCALE strategically and sustainably and step back from the day-to-day so you can focus solely on the parts of the business that need your attention.
