Ask an Anchor: Why am I daydreaming about a 9-5 job?

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I NEVER thought I’d daydream about working 9-5 for someone else. NEVER! But that’s often where my thoughts go these days.

Hi Sarah!

2019 has been ROUGH for me, to be quite honest. I'm on a rollercoaster of wanting to drop everything and quit, but then psyching myself up and pushing forward with my business. I NEVER thought I'd daydream about working 9-5 for someone else. NEVER! But that's often where my thoughts go.

I can't throw in the towel without at least trying to set myself up for success though, I know that. I want to understand my money and get my goals in line.

I have a feeling that the doubts that make me want to set everything up in flames might see themselves to the door once I can see where I'm going.

Thank you!

Conflicted in California 


 Dear Conflicted,

Let's talk about a real problem with the internet's fascination with business ownership. I like to call it: Entrepreneurship Porn. It usually looks something like this…

  • Go out on your own and immediately make six figures

  • Have the perfect branding

  • Obtain the "right" $300 clogs

  • Curate (and afford) the perfect living space

  • Get perfect photos of yourself

  • Also, have babies

  • Feel entirely OK with ambiguity

Easy as that! You're running a successful business!


This whole scene is well-intended, but a farce. And I know from talking to tons of business owners each month that it's causing severe anxiety and sadness. Overall, without real context, the above picture of entrepreneurship leaves people feeling one step behind, always.


Just like embracing real bodies, there is a movement surfacing that is helping us see the effort, pitfalls, and emotional turmoil that come with going out on your own. My work,internally and externally, is to help normalize the path of business ownership, which CAN lead to success. But first, the struggle, learning curve, and the reality of the dream. Have you figured out by now that the struggle is perfectly normal?


What it really takes to run a successful business:

  • Be an expert in your craft or service FIRST

  • Understand marketing

  • Believe customer service is of the utmost importance

  • Be financially literate and savvy

  • Also if you'd like to scale, know how to manage a team

  • Don't forget about that big picture thinking!

  • Also! Remember your family and friends and maybe take a vacation every once in a while.


Frankly, after juggling all of the above (of which I have left out A LOT), sometimes people DO choose to work for someone else. I consider that decision a "win" in and of itself.


A win? HOW? Running your own business is "the dream," right??

If the formula and track seem awful/hard/unappealing, a realization that you don't want to do "all of the above" will save you years of hardship. By uncovering the difficult truth of what it means to be a business owner, you will not only save money but stress & anxiety, which we know cause long-term health problems.


That all being said, I LOVE THAT WHOLE LIST. I LOVE RUNNING MY BUSINESS. I believe wholeheartedly that small businesses are the future. I support and teach them! Small business' success = my success!


Back to you, dear writer — I honestly don't think you're in the "shift back to 9-5 work" category just yet.

The folklore / rule of thumb is that it takes 3 years to reach "profitability," whatever the heck that means. For me, because of my low overhead, my business was "profitable" from the get-go… but that doesn't mean I was making enough to do essential things like save for emergencies or contribute to an IRA (or pay for all of my groceries). To afford the important extras, it took 4 years. Even now, during my 6th year, it's still a lot of work to maintain the income I genuinely need to feel great about keeping my doors open.


So why do I do it? And why should you keep doing it? Find ways to like all of the work. From doing your "craft" to figuring out a growth strategy.


Here are questions you can ask yourself as you start to envision the future:

  • What do I do the best inside of my business?

  • What can I hand off? And/or …

  • Do I have the means or trajectory to hire the right support who can take on the parts I don't enjoy?

  • Can I pay myself enough so I can do more than just survive?

  • Are there success points outside of income?


The category you could be in is one where you need to take a bit of pressure off of your "business" so you can actually focus on it. The pressure usually comes from financial responsibility, learned money fears from your upbringing, or (better yet) the perception of what you should be making.


Let's talk about internal vs. external motivations:

Connecting success with money will always leave you feeling, well, poor. Connecting success with real milestones and achieving creative goals will always be more fulfilling. The true nature of our patriarchal, capitalist society requires you to have money, not just now but later, to make sure that in your twilight years, you're taken care of. If we had a system that supported our health and well-being, we would have a lot more art, less stress, and maybe even world peace. Who knows.


I recently shared my cash flow with one of my lovely "assistants" (let's be real, they're my bosses.) I think they were surprised by what they thought my business looked like vs. the reality. The cash flow is tight, but there's also excellent work on the horizon. Numbers don't lie, but they also don't tell the whole story.


The money will always come and go. There are strategies, but mostly it takes longer to acquire than we hope and keeping it takes a lot of self-discipline. Continuing to pursue your business in a strategic and not-hemorrhaging-money type of way looks different than the stereotype of entrepreneurial success. I want to get you used to the idea that running a business is an energy, not a path to happiness or fulfillment. Overall, though, it can and should be a path to security and comfort.


Sending all the virtual hugs,
Sarah

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