There’s something wonderfully appealing about the phrase be your own boss.
No more asking for vacation days. No more frustrating meetings. No more office politics. You choose the clients, set the schedule, make the decisions and build something that’s entirely yours.
Sounds pretty fabulous.
And it can be.
But entrepreneurship also means that when the website breaks, the client doesn’t pay, sales slow down or something goes wrong at 4:45 on Friday afternoon, there’s a good chance the boss you’re calling is…
You.
Working for yourself can be exhilarating, creative and enormously rewarding. It can also be uncertain, lonely and considerably more work than it appeared to be when you were sitting at your corporate desk imagining your escape.
So before handing in your resignation, it’s worth asking yourself a few questions about the business you’re imagining and the life that actually comes with it.
Do You Want a Business or Just a Different Job?
This may be the most important question.
When you’re unhappy at work, entrepreneurship can start to look incredibly attractive. Suddenly, being your own boss seems like the solution to the manager you can’t stand, the commute you’re tired of making, the schedule that doesn’t work for your life or the company culture you’ve outgrown.
But those are all problems worth examining on their own.
Maybe what you actually want is more flexibility. Maybe you need a different employer, a new role, better leadership or an entirely different career.
Those are legitimate reasons to make a change. They just aren’t necessarily reasons to start a business.
Running away from something isn’t the same as running toward something.
Be clear about which one you’re doing.
Make Sure Someone Wants to Buy the Dream
Passion matters.
Customers matter more.
You may make the world’s most beautiful candles, give brilliant marketing advice or have an idea for an app that you’re convinced everyone needs.
Great.
Now comes the harder question:
Will someone pay for it?
Not theoretically. Not your best friend saying, “I would totally buy that.”
A real customer. With real money.
Before investing heavily in branding, inventory, office space or a gorgeous website, test the premise behind the business. Talk to potential customers. Research competitors. Offer the service on a small scale. Create a prototype. Take preorders where appropriate. Freelance, consult or sell to your first 10 customers.
The goal isn’t to prove that your idea is wonderful.
It’s to discover whether there’s a market for it.
Those are two very different things.
You May Not Have to Quit Yet
Entrepreneurship doesn’t always require a dramatic resignation.
Sometimes the smartest beginning is much less exciting.
Depending on your employment agreement and circumstances, you may be able to consult, freelance, sell a product or develop your concept while continuing to earn a salary.
That gives you the chance to test demand, learn what customers actually want and discover something equally important: whether you enjoy running the business once it’s no longer just an idea.
Of course, understand your employer’s policies and any agreements involving outside work, intellectual property, confidentiality or conflicts of interest before you begin.
The dream may feel urgent.
Your resignation doesn’t have to be.
Then Make the Dream Survive a Spreadsheet
This is where the entrepreneurial fantasy meets reality.
A salary is predictable.
Entrepreneurial income frequently isn’t.
Before leaving a steady paycheck, understand both your personal and business finances. Know what it costs you to live each month and what it will cost to operate the business. Think about how long you could support yourself if revenue develops more slowly than expected and what happens to health insurance and other employer benefits when you leave.
Then look at the business itself. What taxes and expenses will you be responsible for? How much money needs to stay in the company? How much revenue does the business actually need to generate before you can get paid?
Revenue is not salary.
A business bringing in $100,000 doesn’t mean its owner is earning $100,000.
Know the difference before you make the leap.
You’re Going to Have to Sell Something
This one surprises people.
Maybe you started the business because you love photography, interior design, consulting, jewelry, coaching, technology or food.
Whatever your expertise, once you’re in business for yourself, you’ve picked up another job:
Sales.
Someone has to find the customers, explain the value, ask for the business and follow up when the prospect disappears after saying, “This sounds amazing!”
At least in the beginning, that someone is probably you.
You don’t have to become an aggressive salesperson. But you do need to become comfortable telling people what you do, why it matters and what it costs.
If nobody knows about your brilliant business, you don’t have a business.
You have a secret.
You Also Get All the Jobs Nobody Puts on the Vision Board
Owning a business doesn’t mean spending every day doing the thing that inspired you to start it.
There’s invoicing, marketing, customer service, scheduling, technology, insurance, bookkeeping, contracts, taxes, hiring and vendor management.
And email.
So much email.
Eventually, you may outsource many of those responsibilities. At the beginning, however, entrepreneurs often wear a ridiculous number of hats.
That’s why it’s worth asking whether you love only the work or whether you’re also willing to deal with the business surrounding the work.
Maybe you don’t want to handle all of it yourself. That’s fine. But then you’ll need the resources to pay people who can.
Loving the work and loving the business of the work aren’t necessarily the same thing.
Decide What You’re Actually Building Toward
Not every entrepreneur wants to build the next billion-dollar company.
Thank goodness.
Maybe you want a consulting business that gives you more control over your time. Maybe you want to employ 100 people. Perhaps you’re building something you eventually hope to sell, or maybe you want a creative business that produces a meaningful second income.
You may want to work fewer hours. You may want to make more money. You may simply want the satisfaction of building something that’s yours.
All of those can be legitimate versions of success.
The important part is deciding what your version looks like before someone else defines it for you.
Growth for growth’s sake isn’t everyone’s goal. Neither is a giant team, outside investment or a company that consumes every waking hour.
Build the business that supports the life you actually want.
You Don’t Have to Know Everything Yet
Here’s the frustrating part.
You will probably never feel completely ready.
There will always be something you haven’t learned, a question you can’t answer or another perfectly reasonable argument for waiting six more months.
Preparation matters.
Perfection doesn’t.
Do the research. Know your numbers. Test the idea. Talk to customers. Build a financial cushion if you can. Ask experienced entrepreneurs what they wish they’d known.
Then decide.
Maybe the answer is not yet.
Maybe it’s this isn’t actually what I want.
Or maybe, after asking all the hard questions and confronting all the unglamorous parts, the idea still won’t leave you alone.
That may be worth paying attention to.
Because being your own boss isn’t simply about escaping someone else’s rules.
At its best, it’s the opportunity to create something you believe should exist and accept the responsibility for making it work.
Pink POV
Before you quit your job to chase the dream, make the dream survive a spreadsheet.
Figure out who will buy it, what they’ll pay, what it will cost, how you’ll find customers and how long you can realistically go without a predictable paycheck.
But don’t stop with the numbers.
Ask whether you actually want the Tuesday afternoon version of entrepreneurship, not just the exciting version you picture when you’re tired of your current job.
Do you want to sell it? Manage it? Solve its problems? Make decisions when there isn’t anyone above you to ask? Keep going when a month doesn’t look the way you hoped?
Then there’s one more question:
If nobody guaranteed it would work, would you still want to try?
If the answer is yes, you don’t necessarily have to quit tomorrow.
Start building today.
