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Surviving {and Thriving} in My First Year of Self Employment + Action Steps for You

In the last few weeks—yes, just in the last few weeks—I have felt a shift in my work. Things are feeling like they are starting to click and play together. Systems I awkwardly and skeptically created are starting to pay me back in time and efficiency. I’ve loosely put together a team of handpicked people with different areas of knowledge to fill in the cracks. I’ve trudged through a lot of the less-than-glamorous details of self-employment. And I have somehow managed to come out the other side from all of this feeling…peaceful resilience.

Running your own business on its bad days feels like there is a telephone wire line full of cackling ravens pointed in your direction. But on its good days, running a small business is like listening to a harmonious symphony with each of the various instruments complementing the other. Sure, there are still some less-than-ideal days here at Frugal Confessions headquarters, but overall the periodic feeling of wanting to bang my head against the wall has abated.

Running your own business on its bad days feels like theres' a phone line full of cackling ravens pointed in your direction. Click To Tweet

February 1st marks the one year anniversary from when I first left my job to pursue self-employment, so it’s a great opportunity for me to talk about the year and lessons gleaned from wearing lots of hats I never dared to try on before (the troubleshooter, procurement, and hiring hats come to mind).

self employ cartoon

Cartoon is courtesy of Cartoon Resource.

Worked Through the Four-Year Build-Up

I had a lot to sift through from four years of working a full-time job and coming home to work a more-than-part-time job on Frugal Confessions. Over the years I had accumulated piles of articles I was meaning to read, hundreds of “favorites” in my internet folders scattered all over the place, and 200+ unfinished article ideas in my queue. Taking several days to deal with each of these (and having the time to do so) made all the difference. Not only was there a ton of valuable information in all of those piles—it turns out I’m a decent blog curator—but there was a ton of leftovers that needed to be discarded so that I could make room for the now. It’s been a cleansing process to say the least.

Action Step for You: I dare you to work through one of your big, discombobulated piles, getting rid of what doesn’t work for you and implementing what does. You will feel amazing for doing so, and who knows what the extra space and freedom of guilt will open up for you!

I Quit Working Against Myself, and Started Working in Favor of Myself

Working against myself is {mostly} a thing of the past. And it truly took about a year of working full-time on my business to really get to this point. What do I mean by this? I’m talking about maintaining archaic systems that make me work four times as long and probably cause carpal tunnel to develop well before my time, or continually failing to delegate work that is not in my “zone of genius” but that is in my zone of energy suck, or continuing to believe that what I was doing on the side was an actual business when in reality the business part had not really been created at the time of quitting my day job.

I have this uncanny ability to over-complicate things and to create confusion through over-analysis where there doesn’t have to be any. It’s one of those ongoing lessons I’m learning about myself, and being aware of it has allowed me to take action where before I may have just created another mental obstacle.

Action Step for You: Choose something that you are working on. Now, cut in half the amount of time, energy, and effort that you were going to put into it while still producing the same quality you expect of yourself. This is partly what it means to work smarter, not harder, and doing this exercise will open up so much potential for you!

Found and Acknowledged Several of My Weaknesses

Most of you know by now that I grew up on a family dairy farm. We did almost everything ourselves. If the fence was broken, we became fence repairmen (have I mentioned to you how many agonizing times we ended up standing on major highway Rt. 30 with arms extended—a slew of cars building up—in an attempt to coax our cattle back over the broken fence?). Many a summer day was spent watching my father underneath heavy field equipment attempting to fix what was broken, and I was the designated silo-climber (oh Lordy was that scary) to ensure that we did not overload silage. The list of jobs and needs was never-ending: dip stick-getter, salvager, painter, milker, new calf finder, cleaner, feeder, etc.

My point in bringing this up is that it’s taken me awhile to learn that I don’t have to try, or even attempt to try, everything. And as with my fence-fixing example above, it is not to my advantage to continue doing the things that are my weaknesses and likely always will be. Sure, I can get better at something, but it comes at the cost of my most precious resource: time.

Two of my big weaknesses that became brutally apparent to me over the last year are product launches and marketing. After I throw myself into creation of something, I want to unleash it and be finished. But that is hardly how you sell something, not to mention all of the missing marketing work. I have grown ten-fold in both of these areas, but moving forward, will definitely be continuing to delegate some of this work away.

Action Step for You: Instead of trying to conquer your weaknesses or ignoring them all together, acknowledge them. Choose several to give away, and then delegate without shame. You don’t have to be good at everything, and will thank yourself for doing so later!

Redefined My Definition of Success – Finances

I’m a girl who likes to save money. I also tend to value myself by the money I am making. Be it right or wrong, it’s my nature. As such, I’ve had to really redefine my definition of success. This is because at the moment, I am definitely not making what I consider to be full-time income (despite working harder and longer hours than I ever have before).

Initially, I set the goal of being able to pay our mortgage + escrow each month with my net income. We paid off all of our non-mortgage debt in September 2010, so this is a significant chunk of our monthly financial obligations. Over the last 12 months, my net business income has covered 9 of these payments. Gross business income has covered 11.5 of the last 12 months of mortgage payments.

Even though I missed this goal, we were still able to add 28% of our net income to our permanent savings in both retirement and non-retirement accounts in 2013. This is despite me quitting my job two months in, and despite my husband losing his job on Halloween. Even better, this money has not been touched. Granted, this is a percentage I am sharing and we are now working with less money overall. But I’m quite grateful with our sustained savings in light of our substantial decrease in income.

And guess what? It’s not all about the money (I’m saying that more for my sake than for yours). Having the ability to dally in lifestyle design is just amazing, and if we are paying our bills + saving for the future, then there is really no price you can put on these amazing 12 months I have been blessed with. Waking up each day without an alarm at a really early time with a smile on my face is absolutely priceless. Being able to edit this post in my backyard with my two kittens pouncing about is blissful. I hope to never lose sight of these everyday blessings.

Action Step for You: Thinking about starting a new venture or making a big change? Take half an hour or so to think about how you would define success for it. Set some measurable goals for yourself so that you will know if you are meeting this definition or not. And don’t forget to measure in life happiness when thinking about what it really means to be successful.

Invested in My Business with Part of its Profits

The reason why my gross and net business income is so different is because I took opportunities to invest part of my profits back into my business more than in any of the other four years Frugal Confessions has been in existence. And I don’t regret spending a dime of it (that says a lot coming from someone who hates to part with their money)!

Investments included purchasing a new laptop and operating software (my old laptop was a huge handicap to my online business; imagine 30 second delays after each click, chasing cursors, etc.), a soon-to-be-revealed site redesign, hiring my first Virtual Assistant, incorporating Frugal Confessions into an LLC, etc.

Action Step for You: Identify several areas where you could use some investment in your business or life. You don’t need to make these investments all at once, but decide today to work towards investments that will add comfort and ease to your day.

Worked on Delegating, Managing People and Managing Projects

When you begin to delegate and work with others after working on your business by yourself, there are many blessings that come. But there are also a lot of headaches along the learning curve route. For example, I’ve never hired anyone before. Ever. Over the last year, I’ve hired about ten people for various single projects, single duties, and on an as-needed basis. Many have worked their way onto my go-to list for certain things, while just as many have not. Just the act of sourcing a good and trusting person to work with who knows what their capabilities and their limitations are, and who actually delivers (heck, even near the deadline when you need it) is a big deal.

When you begin to delegate & work w/ others after working on your business by yourself, there are many blessings that come. Click To Tweet

Then when you have multiple people working separately but loosely together on a team, it’s a whole new ballgame. I’ve had to learn how to identify the bottlenecks ahead of time, and how to start things early that will likely cause issues so that when it’s crunch time I won’t be stuck for weeks on end (yes, lots of these learnings were painful ones). You have to manage egos to an extent, as well as learn to stick up for yourself—I found these two to be excruciating at times, until I started looking at the work I was doing as an actual business and realized that I had to take my personal emotions and self out of it in order to succeed.

When you have multiple people working separately but loosely together on a team, it’s a whole new ballgame. Click To Tweet

On the flip side, acknowledging when you are wrong is a great character trait. Learning to speak enough of each person’s industry language in order to effectively communicate needs/wants and get accurate quotes is an art. And even when you’re knee-deep in things, when you’re the decision maker you have got to set aside a block of time when someone on your team needs a decision or direction so that they can be working on other tasks parallel with you, and not waiting on you. If they are waiting on you, then you miss out on some of the time-saving perks of hiring someone else.

Did I mention I learned all of this on a shoestring budget? I’d imagine it might have been easier with more money to throw at the situations. But then again, the lessons I learned are priceless (and who wants to spend more money than they have to?).

Action Step for You: When you start a new project of any kind, do yourself a favor and take half an hour to identify any potential bottlenecks. Go through each component/phase of the project, and take notes where you will need someone else to complete a portion of it so that you can hire/find someone and give them enough time (plus a buffer) to complete the tasks (and that includes editing time as it is unlikely things will be done as you had in mind from the first try). Note areas where you do not have the technical expertise so that you can start the learning process early on.

I would not trade these last 12 months for {just about} anything in the world. Being able to work day in and day out on expressing myself through writing and sprinkling the world with my frugal decadence is such an incredible blessing. I’m sure the next 12 months will be even more defining for me and my business.

Thank you for following along and being part of this community! I hope to continue serving you well, and can’t wait to see what’s in store this year and beyond.

Are you a blogger or do you own a small business? Be sure to come back for Wednesday’s post where I outline lots of free resources I found immensely helpful over the last year.

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>>
Behind-the-Scenes of Frugal Confessions' Second Year in Business>>

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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 7th of April 2014

Congrats! This post was very insightful and it sounds like going solo has been the best decision for you. Keep up the great work!


Monday 7th of April 2014

Thank you, Charlotte!


Sunday 9th of February 2014

Congrats on completing your first year! :) That's really exciting. Sounds like you've accomplished quite a lot in a short time. I'm sure the year flew by fast.

I hope to be able to be able to write a similar post as this a few years from now. One of my long term goals is to go from part time to full time blogging.


Monday 10th of February 2014

I will cross my fingers for you (though ofcourse it is not about luck;)). Keep up the great work!

Rebecca @ Stapler Confessions

Wednesday 5th of February 2014

Happy anniversary! I recently moved my desk to a different room, which required going through more than a few discombobulated piles and devising some new systems -- the coupon filing/sorting system definitely needs to be revamped. I devised a stopgap, but I know that I'm still letting some valuable coupons expire because they get buried in the bottom of my desk drawer.


Wednesday 5th of February 2014

Moving (whether a big one or a small one) is a great time to go through things. Thanks for sharing!

Barbara Friedberg

Monday 3rd of February 2014

Amanda, Inspiring. I like the part about systems. I think that's one of the hardest things. I'm working on it!


Tuesday 4th of February 2014

Systems are so difficult to wrap your head around and set up...but they really do make a difference. I am proof of that!


Monday 3rd of February 2014

Congrats on your success! I'm looking forward to Wednesday's post on resources that you've found helpful.


Tuesday 4th of February 2014

I am glad to see you here, Tina.