This is my story about how I became an entrepreneur (after never wanting to have my own business,) how I discovered my true passion and how I created the kind of lifestyle that gives me the freedom to be my own boss, live wherever I want and do more of what I love.

It's a long post, so be ready to read! I wanted to provide valuable insights for you so I tried to be as detailed as possible. 🙂

I hope I can help you figure out what your true passion is, learn from some of the mistakes I made and encourage you to keep chasing after your own dreams! Through my long entrepreneurial journey, I've learned that if you are persistent, patient and never give up, you'll eventually be able figure everything out, create your own dream job and live a fulfilling life you absolutely love!

How I Created My Dream Business and Freedom Lifestyle


I grew up surrounded by entrepreneurs; my grandparents, a few of my aunts, a handful of my cousins, and my mom all ran their own businesses.

One would naturally think I would have wanted to run my own business, too, right?


Running my own business was THE LAST thing I wanted.

I saw first-hand what it was like to run one through my mom, who ran her own boutique for over 30 years. The time, hard work and stress she had to endure for so long just never seemed worth it to me.

I never wanted my life to be consumed by work.

What I did want was freedom, a stress-free life, to live my life on my own terms and to be able to leave my work at work.


I’ve loved to draw for as long as I can remember and so I spent a majority of my childhood doing just that. Being creative was my outlet. If I ever needed to make time pass by quicker, I would find a place to sit alone and just draw stuff; it was something I could get lost in for hours and not even realize it.

Classmates, teachers and family all knew me to be "the creative one," as I always excelled in art projects and other hands-on projects... anything that allowed me to make stuff.

I also loved playing with chalk. I remember having all of these big visions in my head, yet I felt like I couldn't create them on any old piece of paper; I needed larger spaces to make them come alive.

It was kind of a weird thing, but I loved to map out entire towns in chalk on the paved basketball court in my backyard. I remember laying out the roads, parking lots, houses and stores (kind of like the maps you see for theme parks like Disney's Magic Kingdom.) I also loved to draw houses and make layouts of the rooms.

I found it fun to create something, wash it off and then create something else. Something better than the last time.

I think this was about the time when I realized that I loved to organize and format stuff in a way that made everything seem more functional and efficient (website design calling my name?) For a good part of my life, I thought I might end up as some sort of architect and also dreamed of designing my own house one day.

Then there was the computer side of things. One of my uncles had always been into tech stuff and so he introduced me to Adobe Paint when I was maybe 10 years old (circa 1991... old skool days). I remember sitting on the computer for hours, just playing around with it and drawing random doodles with the mouse.

I was 16 when my mom got us our first computer. I remember thinking it was one of THE BEST things she'd ever purchased and, again, I found myself nerding out on it for hours.

This was about the time when I started getting curious about website design.

Somehow, I discovered the Yahoo website builder, which was free at the time, and started playing around with it, creating a website that was all about me and what I liked to do (ahem, I guess it was more like a blog or online profile... destiny calling?!)

I remember having so much fun with it and thinking to myself, "Wow, if I could do this all day and get paid for it, that would be a DREAM COME TRUE!"

Looking back, it's definitely my passion/gift because it's the thing I would do without getting paid, simply because I love it so much. 🙂

A few years later, MySpace popped up and that's when I really started getting into the idea of some day becoming a web designer. I remember designing and then redesigning my MySpace page over and over again, simply because I constantly had all these new ideas in my head and I just wanted to try them out and see what they looked like.

My last semester in college, I took an Intro to HTML course... and I was officially hooked. Web design was definitely what I wanted to do. Creating things online that the whole world could see seemed like the COOLEST THING EVER.


I graduated from college in May of 2003, with a Bachelors degree in Communications from Worcester State College.

After graduation, I moved back home with my mom and got a "temporary" job in retail. My plan was to live at home for 6 months, save up some money and then move from Massachusetts to Florida (I always dreamed of moving to a warm beach city.)

Six months after graduation I decided hold off on moving to Florida and instead went back to school to complete a web design certification program. Once I completed that, I started my own freelance web design business, which I called "Citrus Squeeze Designs."

I only considered this a side business... something I did for some extra income here and there and never really thought I could make a full-time income with it, so I kind of gave up on it after a year or so.

About a year after graduating college, I decided to leave my retail job and finally upgraded to a 9-5 job. Having a 9-5 job was the norm and seemed to be the goal for so many people. If you were lucky enough to land a job that gave you the same schedule as everyone else, you had “made it.”

I enjoyed having my nights and weekends off, because my friends also had nights and weekends off. Naturally, that meant I could spend more time with them, having fun.

For most of my life, living for the weekends was what I lived for.

After being a poor college student for 4 years, I really loved having money to spend and so, naturally, I started spending more of it.

I was all about living my life to the fullest; I traveled internationally, I partied every weekend, I dated around, I ate at new restaurants, I stayed really active and I spent a lot of quality time with my friends.

Choosing happiness meant everything to me, so I just did whatever made me happy!


Six months passed, then 1-year, then 3-years... and then all of a sudden it was 5-years later and I was still living at home, with my mom.

I was 27 and had never lived completely on my own. Plus, I still hadn't gone through with my big dream of moving to a warm beach city.

One day it hit me that maybe it was time to get a little more serious about creating that dream. After all, I hated feeling cold all the time.

I wanted to find a friend to move with, to make the whole thing a little less scary, but most of my friends weren't open to moving away from their family... or their comfort zone.

So I had a decision to make: Stay and be miserable because no one shared the same dream or face my fears and see what happened.

I decided their reasons for not wanting to move were not enough to make me stay. I wanted to be happy and I wasn’t going to let anyone else, including myself, stand in my way of that.

So I made the decision to move 3,000 miles away to the opposite corner of the country... because if I was going to create this big dream of mine, I couldn't go small. I had to go BIG.

I decided on the city of San Diego, because beaches, palm trees and sunny weather year-round sounded like my dream life! Plus, everyone there seemed so active and outdoorsy, which fit my personality perfectly. 🙂

Once I made the decision that I was going to move to San Diego, I realized that I needed to save up a good chunk of money. I wasn’t making much at my current graphic design job so I went looking for a better paying job. I found one, got hired, quit my old job, and started working my big plan. My big plan was to save half of every paycheck for 1 year, or until I had $12,000 in my savings account (buffer money.)

So I did that and quit that job in February of 2009.

Two weeks later, I packed up my little Jeep with whatever I could fit in it, and started driving across the country, by myself. I had no job or place to live lined up, but for some reason, I felt confident I could figure that part out when I got there.

I decided to turn my drive into a 3-week adventure and made plans to stop in various cities along the way, visiting friends and family where I could, and just exploring. It was one of the best trips of my life because it really boosted my confidence and made me feel really empowered!

I did something big that I was afraid to do, and I succeeded.

When I got to San Diego, It took me about 2 weeks to find an apartment and about a month to find a part-time job that would hold me over for a bit until I found something full-time.

Five months later, in August of 2009, I landed a full-time graphic design job, which helped me feel a lot more financially secure and “settled in.”

I spent the next year partying, traveling and having fun with all the new friends I made, every chance I got… it was a celebration afterall! I was living in my dream city and living my dream life!

After working at that job for a year, I started to realize how shitty the management was treating all of us employees. Not to mention, they paid us crap. I only stayed because the economy was down and I felt like I was lucky just to have a steady, full-time job.

In October 2010, they decided to cut my hours from 40 hours to 20 hours a week and that’s when I decided it was time to get out of there. I had no reason to stay, after all… I couldn’t survive on part-time pay and I definitely didn’t want to be treated like crap anymore.

So I found a new graphic design job in November 2010, that paid me a bit better and treated me a hell of a lot better. I loved the people there and found the work to be decent, but after about a year and a half, I started getting bored and started craving something a bit more challenging.


For about a year and a half, I was in a relationship with an emotional abuser, yet I didn’t realize it (you never see it until you’re out of it.)

In June of 2012, he broke up with me out of nowhere.

We were living together so one of us had to move out. I decided to be the one to leave simply because I was heart-broken and couldn’t bear living in a place that reminded me of him.

I spent the next 2 months searching for a roommate on Craigslist and ended up moving in with a girl named Amrita who ran her own successful website design and online marketing business.

At the time, I had no idea that this girl was about to change my life.

The whole break-up and moving situation sucked at the time, but looking back, it was such a blessing in disguise! I am now SO grateful that my boyfriend broke up with me when he did, because otherwise I wouldn’t have met her!

Amrita was pretty much living the dream life, in my eyes. She could work from home or anywhere that had wifi, she had a flexible schedule, she was her own boss and she was making bank!

Over the next few months, she really opened up my mind to all sorts of new possibilities in the realm of entrepreneurship. Plus, her story and the way she was choosing to live her life was really inspiring and motivating to me.

This is when I began thinking about starting my own business, too.

I wanted to be able to work from home (or from anywhere), I wanted to have a flexible schedule, I wanted to do work I actually loved and I wanted to do something that really challenged me.

I also felt like I needed a project to work on, to help me get my mind off of my ex. He had been stringing me along for months after the break up, which didn’t help at all in my healing process.

In October of 2012, I decided I wasn’t going to let this toxic person hold me back any longer. I desperately wanted to move forward, so I made the decision to cut him off and go no contact. 

A month later, my job announced that they were going to be downsizing and were offering severance packages to anyone who wanted to leave.

I saw this as my opportunity to pull myself out of my sadness and boredom and to start working towards something bigger: creating a better life for me.

So in December of 2012, I took my 6-week severance package, quit my job, and with a little help from Amrita, I started my own graphic and website design business.

I called it Whipped Dream. 🙂


When I first started out, I quickly realized I had absolutely no clue what I was doing. I didn't know how to get clients (or rather the right clients,) I didn't know how to price my services correctly, I didn't know how to collect payments efficiently or how to run a business in general.

I remember wishing I could find some sort of guide online that showed me the steps on how to get started or where I could find a list of recommendations for tools and resources that would help me create and grow my business.

Amrita gave me some tips here and there, but since I like to do things my way, it was rare that I actually listened. I also hated asking questions because I didn't want to feel like I was bothering her, and so I always just tried to figure everything out myself (at least I had the confidence in myself that I could do that... or maybe it was a touch of arrogance. Who knows.)

Looking back, I can see now how much I got in my own way without even really realizing it. 

Because I was always getting in own way, I found myself having to work ALL-THE-TIME (doing design work for low-paying clients plus trying to juggle a bunch of other part-time side jobs). I was always feeling overwhelmed and stressed out... how was I supposed to keep this up? How long was I going to be able to keep this up?

I was feeling miserable, my health was declining and my sleep patterns were greatly suffering. The first 9 months in business, I had insomnia and for most of those months, I slept maybe 2-3 hours a night, if I was lucky.

I was working myself into the ground, and yet I still wasn't making enough to pay my bills each month. In fact, after 2 years in business, I ended up racking up almost $40,000 in credit card debt.

Needless to say, the first couple of years were pretty f*cking rough for me.


Before I started my business, I had only used Dreamweaver to design websites on. Amrita told me I should learn how to design sites using the WordPress platform because then my clients would be able to go in and easily make their own changes once the site design was finished.

I figured she had a good point, so I sat down and taught myself how to use WordPress the free way... through a variety of Google searches, YouTube videos and lots and lots trials and errors. Although that learning curve was a bit challenging, looking back, it was probably the easiest thing to learn over all.

The things that came after that were much more difficult for me to wrap my head around.

I remember imagining that once I designed a pretty-looking site for myself people were going to instantly notice it and be in awe of how great of a designer I was and like magic, I was going to start getting all these inquiries from people who wanted me to design awesome websites for them as well (haha, I'm shaking my head and laughing as I write this because I can't believe I truly believed this!) 

Actually, I'm sure most people believe this.

I've learned over time (and suffering!) that having a pretty website is simply not enough.

For starters, people need to be able to find your website.


SEO, or Search Engine Optimization, is a technique used to help search engines and potential customers find you online.

Amrita told me from the beginning that I needed to learn this but it just seemed too confusing and difficult so I never managed to get around to it. I figured I could learn it later when I had more time and for now I could just create business cards, flyers and free ads on Craigslist to help get the word out about my business.

Looking back, NOT learning and applying SEO was probably one of my biggest mistakes.

I believe my initial marketing and advertising choices ended up cost me more money in the long run, as they required a lot of time, effort, and energy from me, on top of everything else I was trying to do.

After 2 years of working my ass off and spinning my wheels, I found my self spiraling downward into the land of burnout.

In December of 2014, I hit my personal rock bottom and decided that maybe it was time to give up on this entrepreneurship thing and start looking for a 9-5 job.

While I was laying around my apartment, wallowing in my own misery and overwhelming feelings of failure, I remembered Amrita telling me how important SEO was for business. I had this SEO book that she actually gave me when I first started out, yet I hadn't even opened it. I figured since I wasn't doing anything else that week, what better time than now to start reading it? What did I have to lose?

I ended up reading a good portion of the book and found that I actually understood it. Then I started applying what I learned to some blog posts I was writing and included some affiliate links. Almost immediately, I started seeing more traffic on my sites, and over the next few months I began making more money in less time and with a whole lot less effort (passive income.)

Game. Changer.

Learning how to do SEO was my big turning point and because of it I never ended up having to go back to a 9-5 job. In fact, I ended up quitting all of my side jobs a year later and by 2016 I was fully working only for myself, doing what I loved and from wherever I wanted (H-E-L-L-O TRAVEL BUG.) 😉

In addition, I felt a lot less stressed, I didn't have to work as much and I finally felt like I had found my true calling... branding, website design, blogging and online marketing.

A year and a half later, I have been able to pay off all of my credit card debt ($40,000) and and am now officially DEBT FREE! Literally, one of the best feelings IN.THE.WORLD.

Since I started out, my income has basically been doubling itself every year, and about 90% of what I make is passive income, which majorly helps support my freedom lifestyle. 🙂


I've always preferred to do everything myself because I've always felt like that's the best way I learn. However, I've learned from doing everything myself that that is not always the smartest, most efficient way to get ahead.

As a result, I've learned a lot of lessons the hard way; from making mistakes that cost me BIG money (ahem, not learning SEO right from the beginning,) to spending lots of time trying to find the answers to things. Spending time trying to find answers has proven to be more of a loss than spending money on something that's going to get me the answers quicker and in a more organized fashion (and time is more valuable than money, right?!)

I'm pretty conservative with my money and I don't like spending it on things I can do myself, but I've realized that once I have the know-how, I can make bigger money that much sooner and the cost of whatever it was that helped me learn has usually paid for itself, and then some, almost immediately.

That being said, after the results I got with SEO, I really started making business investments a priority.

One of the biggest investments I made, was an online business and blogging course for $500. This course taught me things like how to define my niche and target market, how to brand myself better, be more productive, create systems of automation, grow my traffic online and strategize better overall (to name a few.)

It was one of the best investments I ever made and since then I've been able to see continual improvements in all of my blogs and businesses, as well as my general lifestyle. 🙂

To this day, I continue to invest in all sorts of ebooks, business books, webinars and other online courses simply because I love to learn and I love the process of continually improving! Plus, staying on top of trends helps increase my wisdom so I can help others better! 

In addition, all of these things can be used as business expenses!


Initially, my target audience was any small business, entrepreneur or start-up and my goal was to provide custom design services at cheap prices. I simply wanted people to walk away with something amazing and to feel like they just got a great deal.

My first few years in business, I would do any kind of random design job (even things I didn't know how to do/like to do,) for cheap and for anyone who contacted me, simply because I felt like I was lucky enough just to have someone want to work with me! I only accepted those projects because, frankly, I was desperate. I desperately needed money to pay my bills.

There were a few problems with this: I was getting lower-quality clients who demanded more of me, yet paid me less and usually not on time. Also, they never really seemed to appreciate my ideas or my work, which really sucked after working my ass off for them.

Talk about draining and selling myself short.

For a while, I absolutely hated doing design work for clients. So much so that I actually stopped all client work at the end of 2016.

This was when I decided it was time for me to take a break to do some self-reflecting. I needed to work on gaining some clarity on what I truly wanted to be doing and who I truly wanted to be helping.

I knew I could create (and wanted to create) quality work that went above and beyond people's expectations, but I needed to work on projects I actually liked doing and naturally excelled at. I also knew that because of this, I deserved more. More money, better clients, happier experiences and to make a bigger impact.

During the first half of 2017, I realized that I didn't want to stop designing or being creative, as that was my true passion, but I did want to do work that was more fulfilling. Something that was bigger and more impactful.

So, as I learned in that online blogging and business course I took, I knew my next step was to define my target audience. I started by writing down exactly what I imagined my dream client to be like, which included things like their age, gender, marital status, current occupation, income level, personality, philosophies they live by, dreams or fears they have, their interests and their pain points.

After all of that, I decided that I simply wanted to focus on helping others who were a lot like me; ambitious women who wanted to create their own successful businesses around their own passions. Women who also wanted to live this freedom lifestyle of working less and living more. 

As an introvert, naturally I crave having deeper connections with people... people I can relate to. And I prefer quality over quantity.

Doing small, random projects for strangers wasn't fulfilling for me. When I don't know someone, it's harder for me to understand their personality and style and therefore it takes more work and time to create what they are looking for, which can be really frustrating.

I like working with women because naturally I can relate to them better, which makes our work process flow better. Plus, my style has more of a "feminine" nature to it.

I realized I wanted to develop relationships with fellow badass boss ladies and really dive deep into helping them create a brand; something that would change their life as well as the lives around them. And I want to teach them how to help themselves stand out and be big influencers in the world by using their own unique inner strengths, gifts and talents!

The current clients I work with are all amazing, and I believe that has a lot to do with how I've defined my niche and target audience. We're all ambitious females with our own businesses. A lot of us are perfectionists and very detail-oriented. We work hard but still enjoy life. All that being said, we work well together because we can relate to each other. I'm happy. They are happy. Everyone is happy 🙂 


As an entrepreneur, I think it's really important to know your WHY because that is what is going to drive you and motivate you to keep going, even on your hardest days.

I personally don't ever want to feel controlled by anything or anyone, whether that's a job, a boyfriend, a friend or even a parent. I also don't want to feel like I need someone else to make me happy or to support me financially; I want to be able to do all of that for myself.

The way I figure it, the more I learn and the more I can do myself, the less other people will be able to have control over me.

What drives me day in and day out is progression; always moving forward, learning, growing and improving. All of the little things I do each day are all going to add up to something big one day.

"When we strive to be better than we are, everything around us becomes better, too."

I don't want to settle for who I am right now. I want to create who I want to become.

I want to surround myself with like-minded people who force me to level up, and stay away from the people who try to hold me down.

My WHY is to create a better me, a better life and to be the one in control of my own happiness.

My ex promised me the world, full of traveling, money and living the dream life.

And he fell short of that. Wayyy short.

Instead of wallowing in sadness for the rest of my life or trying to find another guy who could support me, I chose to turn my pain into my power and went out and created my own success. And that is something that can never be taken away from me.

Don't get mad. Don't get even. Do Better. Much Better. Rise Above. Be so engulfed in your own success that you forget it ever happened.


This business is my baby and I have so many ideas on what I can create!

My main service will be branding + website design for those who are looking for help creating their brand and online presence. 

To satisfy my obsession for organizing, my vision is to catalogue all of the things I've learned over the past 5 years of entrepreneurship, in a simple, organized and fun way. Things like blogging tips, branding tips, business tips, marketing tips, and DIY tutorials.

I also plan on creating a resource of premade logos, brand packages, templates, guides and worksheets to help you learn how to grow your business!


My goal was always to have more freedom to do what I love, to live with the least amount of stress and to live my life on my own terms. Now I am truly doing it and it. is. AWESOME.

Every day, I wake up happy and excited because I know I have the freedom to spend my day doing pretty much whatever I want, when I want. 🙂 Since I love to learn and be creative, a majority of my days are spent doing exactly that.

My friend Amrita had a huge impact on me, as she inspired and encouraged me to create something for myself that completely changed my life for the better... and for that, she'll forever be a big part of my success story!

I've discovered, over time, that I have a huge desire to be part of other women's success stories. 

I am truly passionate about helping other women rise up and create successful businesses around their passions. I love seeing fellow girl bosses chasing their dreams and doing whatever it takes to make themselves happy!

My work now has a purpose and I'm truly living my passion and my dream lifestyle!

If you've been thinking about making that jump, I say DO IT! You only live once... might as well GO ALL OUT!

If you do not jump your parachute will never open. You may be safe but you will never soar.


I've spent the past few years documenting the ups and downs of my own entrepreneurial journey on my personal blog. Below are some links to things I've written that I thought could be beneficial to my fellow female entrepreneurs out there. If you can relate to any of my stories, comment below! I'd love to find more ladies out there chasing their dreams!

With Love, Tara Tierney

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