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  • Writer's pictureThe Gaitatzis

That Place in Taking Leaps o' Faith

A friend of mine asked me a question recently: 

"I’ve been thinking a lot lately about my desire to create a business and work for myself, and the roadblocks I feel are preventing me from doing it. Namely, finances. I know you’ve had your ups and downs on this subject. Wondering if you have any resources to point me in the right direction.

At this point I can see how I could strategically move up the ranks at [current employer]. It will take time and patience. In the meantime, I have this fire to create something myself that I’m afraid might die if I let myself get too comfortable working in the “safe zone.” I’m slowly chipping away at debt, but wondering what it will take for me to make the leap to working for myself.... Big questions, I know."

My answer to her was easy to give, and I thought it'd be helpful to share with others, too. So I told her... 

"To tell you the truth, I've always had something on the side while working for an employer. 2013 it was at grad school as an Resident Assistant in the freshmen dorms, then 2014-15 as the dorm manager, 2016 at SoMa StrEat, 2017-19 at Nextdoor. But all along, I was planning at least 5 events per year. If I wasn't hired for a period of time, I was just creating my own projects (styled shoots a.k.a. fake weddings with real vendors and submitted the shots to magazines for marketing etc).

After 4 years of this "side business thing," I broke down the costs and looked at my profits. I was making thousands, but not tens of thousands. That's after investing in Facebook ads, travel (Zipcar), a hell of a lot of time, paying for assistants, etc. So, it wasn't worth it for the money, but it was worth it for the experience because now I know a lot more people, and (more importantly) they now know me - so there's a community around me - and that has been worth the investments I've made."


There was a phase of life when I prayed for God to give me more time... and through a series of experiences, I learned that the answer was to give time more me.


"To answer your question about resources that helped me save up, there are a few - like a combination of things:

1. Doing the Landmark Forum (I didn't have a lot of money to pay for this) - it shifted my mindset to get me thinking how I think about my life and goals today.

2. Living with close friends for a few months just outside of San Francisco was really helpful for saving on rent. Sometimes, simply asking for what you need can make the difference. Community may be more willing to help more often than we realize!

3. Relatedly, I found neighbors in my much broader region via Trusted Housesitters, where I found folks who needed a sitter for their pet (or just their house), in exchange for me being able to live there for free.

4. Reframing and then rebranding my business to make me more money. I got to know what kinds of people wanted my wedding services: They didn't want me to plan for them - they love DIY; they actually wanted me to guide them and equip them with the tools they'd need to plan their own wedding. I realize that I didn't need to restrict this service to the Bay Area, but I can create webinars that would be available to couples like this around the US (and the world, probably). So I'm now focused on creating webinar content and launching webinars this season (before the summer).

I'm in debt, too. Like, $85k. Thank you to MBA school, which I'm still trying to justify... it certainly hasn't been the leading reason for landing any of the jobs I've had, nor landed me a recent, decent job yet. Anyway. So, I'll need at least 85 couples to pay for my webinar once I launch it, in order to pay off that debt. Only 85?! (My webinars will be $997 at minimum, with an option to pay in full or opt into a payment plan). And I know that I can find 85 couples in the whole world who will want the webinar.

What it ultimately came down to was:

1. Finding out how much time I have to work on this side gig

2. How much money I'm willing to spend (for Facebook ads, software, podcast microphone, virtual assistant, etc.) to equip me with what it takes to launch this thing

3. How happy, confident, motivated and committed I am to do this

4. Creating a plan for the minimum I'll need to do to achieve what's important to me (a.k.a. how many sales I need to make to pay off my student loans - that's what's important to me right now)

5. Commit to said plan, and don't beat myself up too badly when I have a bad day or feel like I've wasted time on something else instead of work.

Other resources I recommend are:

1. Women-centric Facebook groups - I love the encouragement, inspiration, feedback and accountability I've found in other women

2. YNAB (You Need A Budget) is another Facebook group I discovered - really great concepts and tips for how to manage finances

3. Absorb. It's a free, 3-min daily talk that one of my previous coaches launched. I love listening to them because they inspire me to create actionable items and intentions everyday for myself.


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