Do You Really Want to Be Your Own Boss?

These are the heroes and demigods of modern capitalist mythology.

We tell and retell their biographies while venerating their awe-inspiring works.

If there is such a thing as “winning” the game of life, most people would say this is it.

Our media is fairly obsessed with entrepreneurs, whether it’s Shark Tank inventors, celebrity restaurateurs, march-hawking bloggers, or makeup tutorial moguls.

We’re bombarded with messages that suggests that entrepreneurship is the only path to real wealth and fulfillment.

Everyone feels the pressure to quit the day-job, reach for the stars, and be your own boss!

But as any successful entrepreneur will tell you, it’s not for everyone.

The autonomy and independence can be fulfilling, but you’ll probably be working longer hours for less money—at least at first.

And having a great product idea or visionary artistic talent is just one small element.

Whether you want to be a freelance graphic designer, an Instagram influencer, or the inventor of a squirrel-shocking bird-feeder (oh it’s a thing…look it up), most of your time will be taken up with new tasks and duties that you may or may not find enjoyable.

So before you quit your 9-to-5, let us show you some of the many hats you’ll have to wear if you want to be your own boss.

So, you think your cupcakes are the bomb and decided to start your own business?

Congratulations, you’re not just a baker anymore.

Now you’re a CFO!

Cash is the lifeblood of any business and no matter how much people like your product, if you’re not balancing revenue and expenses correctly, your biz will bleed out.

The two main skills a CFO needs are Budgeting and Accounting.

Budgeting is deciding how to spend your money to get the most bang for you bucks.

It means being realistic about what you have to work with, and eliminating waste wherever possible.

If you’ve never kept a personal home budget you might want to start to get some practice.

Accounting is minding your business’s financial records, which includes tracking your income and costs, estimating your quarterly taxes, and maybe even payroll.

You’ll probably have to learn an accounting program like Quickbooks, or maybe hire a bookkeeper to lighten the load.

But most entrepreneurs will tell you that you’ll always have to be involved.

No one will care about these numbers as much as you do.

In addition to being CFO, you are also now the head of your company’s Human Resources department.

That means you’re in charge of hiring, firing, training, delegating tasks and responsibilities, as well as figuring out payroll and benefits for your staff.

What’s that?

You don’t have a staff yet?

Yes, you do: yourself!

Leaving a salaried position means finding your own health insurance, selecting your own retirement plan, and picking up the slack for payroll taxes that you used to split with your employer.

When it is time to bring on employees, finding talented and dedicated people—and keeping them happy—is essential.

Many entrepreneurs credit their success with being able to attract and retain employees smarter than themselves.

There are lots of awesome books and podcasts on assembling and managing teams, and we’ll make sure to share our favorites in the doobleydoo.

As a supervisor, you’re not just a manager of people, but also of time.

Time is money, as they say, and making sure that neither you nor your employees are wasting it is crucial.

Our friend Chelsea over at The Financial Diet wanted to give her two cents on the biggest lessons she’s learned when it comes to managing time.

So here's what I did wrong when I first made the jump to being an entrepreneur.

I tried to force a "normal" schedule.

It made me feel like I was working harder if I forced myself to work into that 9-5 even if that wasn't when I was getting my best work done.

I would save the "easy" little things for last because often when I didn't have a fixed timeline throught my day that meant just pushing off the tasks that I didn't really want to do and felt like I could do later.

And the third thing I did wrong was forcing myself to have bigger chunks of "offline" time.

Essentially, taking weekends and vacations as the time when I would totally unplug.

And this is how I fixed them: Instead of forcing myself to fit into a 9-5, I leaned into the times that I did my best work.

And in many cases, for me, being a night owl that meant getting work done at night when my brain was thinking its best.

The fact that you're able to set your own schedule, as an entrepreneur or self-employed person, is something you should take advantage of not fight.

Secondly, I started doing all those easy little things FIRST thing in the morning because I found that when i got them right out of the way I felt accomplished and that sense of accomplishment snowballed into being able to take care of bigger and bigger tasks.

And plus all that little easy stuff didn't keep falling to the bottom or get kicked down to the never slot on my to-do list.

And lastly, I started spacing out my offline time giving myself dedicated chunks, even throughout my day, where I was away from my computer and specifically forcing myself not to work.

When you don't have dedicated work days and vacation days you can constantly be pressuring and guilting yourself into getting more and more work done.

And ultimately that leaves you more drained and unproductive So by dedicating those offline times throughout my day and throughout my week I was often feeling refreshed and not like I had to force every minute into a work minute.

The next hat you’ll wear is a big one: Marketing Director.

Attracting customers to your brand is an enormous job!

You’ve got to conduct market research, create & test advertising, design promotional materials, manage social media accounts and more!

And no, a few random posts on Instagram aren’t going to cut it.

Marketing is a complicated, multi-layered discipline that involves statistics, psychology and art.

If you’re lucky enough to afford it, you can hire a specialist to help you, though many small business owners have to figure it out on their own at first.

Luckily, there are plenty of free resources, like this episode on Market Research we did a few weeks ago!

For many new entrepreneurs, the hardest realization about marketing is that the job is never done!

Even if your product is a stone cold hit, you will always have to keep reminding people about it!

Even Coca Cola still advertises.

Once your head of marketing has attracted a bunch of potential customers, it’s time for your Salesperson to seal the deal.

(That’s you again.)

If marketing is your public image, sales is your personal relationships with customers.

Being a good salesperson doesn’t come by intuition, but by honing and practicing skills, like active listening or networking effectively in a room full of strangers.

You’ll also need to learn how to roll with rejection without taking it personally, and how to create a repeatable step by step process that nurtures potential customers all the way from initial interest to the sale and beyond.

And finally there’s — — wait…”finally!

?” There’s so much more we haven’t talked about!

There’s logistics, customer service, legal!

Not to mention hard-to-nail down “soft skills” like keeping yourself motivated and dealing with irregular income.

I know, I know, but while we don’t want them to have rose-colored glasses, we don’t want to totally scare them off!

Honestly, so much of this can and will come with time and experience if you have the fortitude and patience.

And if this doesn’t sound like it’s for you, that’s okay!

For many people, having a solid day-job that they enjoy can be more fulfilling—and less stressful—than wearing all these hats at once.

And that’s our two cents!