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Behind-the-Scenes of Frugal Confessions’ Second Year in Business

Testing boundaries. Check. Business mood swings. Check. Growing independence (while simultaneously counting on the mercy of others to help me with basic needs). Check.

Yup…I just wrapped up my second year (aka the Terrible Two's) in business. Can you tell?

Okay, so saying it was the Terrible Two's isn't entirely accurate, as it wasn't really terrible at all. You won't find any petulance, tantrums (or at least no big ones), nor obstinate refusals here.

The earth has officially rotated around the sun one more time since quitting my 9-5 job which creates a great opportunity to give you a little behind-the-scenes of my biz.

And if you're not particularly interested in the biz side of things? I want to show you that following the financial advice I lovingly tout here will lead to really cool outcomes, like being able to design your life (i.e. for me, that meant quitting my day job two years ago to pursue my passion).

We're talking about life-changing stuff!

Let's get started with what the second year in my biz looked like.

Honing My Focus

When you put in the work of experimenting, focusing, drilling down, and figuring out what exactly both you + your biz stands for, things get easier. Much easier. Yet while I was in the midst of doing all this (granted, I will always be in this step to a degree) I started to question the process.  From time-to-time, questions like am I doing this for nothing? Will it ever get easier? Will the overwhelm subside and I'll build something sustainable flipped through my mental rolodex.

It took awhile. For sure. But I'm on the other end of what I consider to be a much more focused business. I could literally cry thinking back to those moments of pure self doubt. I wish I could extend that person a warm hug to let them know that, yes, all of my seemingly endless work would culminate into something much more manageable in the not-too-distant future.

Refining My Systems and Learning to Manage, Delegate, and Ask for What I Need

I've taken Chris Ducker's  advice (whom I got to meet this year) of diligently working on my business, not in my business. This included an overhaul and build-up of systems. Amber McCue's How to Clone Yourself DIY course was instrumental in making this Type-A gal feel okay about handing over the reins on things I should not be working on.

And I took it two steps further this time — both hiring a new VA (third time's definitely a charm in my situation!), plus uploading all of my operations documents to Google Docs with shared access. This, combined with a free program called Asana, is how my VA and I can communicate with each other on projects, tasks, and deadlines (you bet I'm a deadline gal).

The system works beautifully, not least of which because after working with two initial VAs on an ongoing basis, I was able to hone in on better learning how to ask for what I need and want. That was no small learning feat!

A Personal Biz is As Much About Launching Myself as it is About Launching My Work

Folks, I can confidently tell you that launching your work out into the world is scary stuff. Like gut-wrenching at moments. And yet, by not launching your work, you're A) depriving others who need your help, and B) not going to be in business for long.

Over the last year I've gone through three major launches. I set up all the tech work myself, which meant there was a huge learning curve. I created everything from scratch with ideas that had been floating around my head for too long. persevered. And yes, I got better at the second one than I was at the first, and after the third launch I can {almost} confidently say the next one will be even easier!

Demarcating Boundaries

I'm a people-pleaser. Whew, glad to get that one off my chest. It's something I'm learning to accept, and to grow from (which is a lot easier to do after undertaking the accepting part).

At the same time — and I suspect this happens to lots of people who grew up on a family-run dairy farm — I have this uncanny ability to work myself into the ground.

I am so pleased to report a major shift in both of these areas (for the better) due to setting up some boundaries with myself + others and sticking with them. It's amazing what setting “I-close-down-my-laptop-by-5:00” and “I-don't-work-weekends”  and “I-don't-have-access-to-email-on-my-smartphone-by-design” boundaries can do for your personal plus business life. It leads to more time and energy, more balance, a better grasp on prioritization, and just an overall sustainability that I've been hoping to achieve (but honestly didn't know if I ever could).

Healthy boundaries don't stop there; they also include price boundaries, accessibility boundaries, not-using-your-brain-as-a-garbage-disposal-of-free-info-gathering boundaries, etc.

Making Investments in Myself + My Biz

I've sorely underinvested in my business. It's because I like to hold onto my money (surprise, surprise!). So I'm really proud of myself for making real, meaningful investments in my biz this past year.

  • Tech + Sanity Updates: If you've been reading these updates all along (scroll down and you'll see the documentation of my small biz journey), then you know that the bane of my biz-existence has been tech stuff: setting systems up for my courses, website launch tech, running a blog, and all that jazz. One of the major investments I've made over the last year that cost a lot less than I thought it would was to stop fooling around with something I find intimidating and (at times) crippling. I now have my website hosted on Pagely.com ($24/month), which is a hybrid hosting solution (meaning there are people there to work as an admin on my site). This, coupled with signing on with WPCurve ($69/month), where they will complete any number of tasks that take less than 30 minutes that I want per month, has made my online life so much easier.
  • Website Rebranding: You'll also notice the investment I made into rebranding my website (old version is below). I had a vision over a year ago for how I wanted to move forward with my brand and your user experience (all of which came about because of honing my focus), and was able to hire a graphic designer/coder to bring that to life.
  • Writing + Copywriting Course: The investment in learning that I've made this past year has been hugely rewarding. Signing up for Courtney's TKO Copywriting Course was the #1 course investment that I made for my business. I was in her first round, put in a lot of work, and my writing + biz confidence has grown immensely.
  • Mastermind + Much More: I also invested in Amber McCue's Fresh Forward (you can try out her awesome stuff for free by signing up for the NiceOps Planathon she hosts each year), which catapulted my get-it-doneness (and trust me, I already had a huge dose of that running through my veins from my background in milking cows and shoveling manure). On top of that, I've gained huge efficiencies and biz-related prioritization thanks in part to Amber's Fresh Start 2015 business plan + 90-day Action Plans.

Second Year Financial Update

Businesses and hobbies are two separate things. The fact is, I wanted a business and I had to create it (and am still creating it) from a hobby that happened to earn some money. Huge difference I learned early on after I quit my 9-5 job.

Businesses and hobbies are two separate things. Click To Tweet

So how is our household faring financially?

In December 2013 I formally separated out business finances from our personal finances. Yes, I've always declared the proper income and expenses separate from our 9-5 jobs. But up until that point taxes were more difficult than they needed to be. Not only that, but it's easier to keep your head in the sand about your actual profit versus expenses when everything isn't laid out. I incorporated my business, then set up a proper business checking and savings, and linked everything up to GoDaddy Bookkeeping. This means that for the entire year of 2014 I was able to quickly track my biz finances.

What a blessing this has been!

I can confidently say that my business profit paid for 10 of the last 12 mortgage + escrow payments for our household (our only debt).

You'll recall Paul was unemployed for a total of 5 months spanning the last two months of 2013 and the first three months of 2014. He started his new job in March. Though underemployed, he is continuing college full-time which means we also receive a housing stipend + full tuition/books paid for by his GI Bill. All in all, we were able to sock away 23% of our income into our permanent savings even with the my business still not making what I consider to be full-time income.


I think the most surprising thing after these two years is the self evolution that naturally occurs when you build a business. I never knew or expected such rapid personal growth from quitting my steady paycheck and challenging myself in such a deep way. It's pretty amazing. Putting yourself out there, challenging your beliefs, facing your fears–because in the end if you don't, you won't make it–really changes you. And I could not be more satisfied with where I am at this exact moment. Here's to the next two + beyond!

Catch-Up On My Documented Self-Employment Journey (spoiler alert: there's a layoff, a few tears, lessons learned, financial changes, and all sorts of goodies that occurred after I pulled the plug on my 9-5):

I Have Chosen to Chance the Rapids: Taking My Writing Full-Time>>
Blogging and Writing Full-Time: Financial Changes to Come>>
Blogging and Writing Full-Time: One Month Update>>
Self-Employment Update: Six Months After Taking that Leap>>
Contingency Plan “Husband-Lost-His-Job” is in Full Swing>>
Update on the Unemployment Situation in Our Household>>
How We're Handling Health Insurance in Unemployment>>
Surviving {and Thriving} In My First Year of Self-Employment>>
What We Did to Financially Survive 5 Months of Unemployment + a Free Gift for You>>

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Amanda L Grossman

Personal Finance Writer and CEO at Frugal Confessions, LLC
Amanda L. Grossman is a writer and Certified Financial Education Instructor, Plutus Foundation Grant Recipient, and founder of Frugal Confessions. Over the last 13 years, her money work has helped people with how to save money and how to manage money. She's been featured in the Wall Street Journal, Kiplinger, Washington Post, U.S. News & World Report, Business Insider, LifeHacker, Real Simple Magazine, Woman's World, Woman's Day, ABC 13 Houston, Keybank, and more. Read more here or on LinkedIn.


Monday 2nd of February 2015

Congratulations! I'm currently in the middle of year 2 of having quit my job and am experiencing a lot of the same things . Especially with boundaries - they've become my best friend!

Amanda L Grossman

Tuesday 3rd of February 2015

Hey Amanda! It's nice to hear from someone at around the same place as me:).