Have you ever envisioned a life liberated from the mundane, where your work ignites passion instead of dread? A life meticulously crafted by your own hands, so fulfilling that it eliminates the constant yearning for an escape? For the past four years, this has been the very essence of the dream my husband and I have relentlessly pursued. Today, I’m thrilled to share that this life is not merely a fantasy; it’s a vibrant reality, challenging yet incredibly rewarding.

Stepping away from my usual recipe content, I want to delve into a topic deeply personal and close to my heart: our entrepreneurial journey. I’ve contemplated writing this post countless times, eager to offer genuine advice and insights to anyone considering the leap into self-employment. My hope is to inspire more individuals to courageously pursue their dreams. While I may not be a seasoned orator, I trust that the sincerity of my message will resonate, offering a beacon of encouragement to someone navigating their own path. For those unfamiliar with our story, let’s start with a brief recap.

Our Journey to Self-Employment: From Fear to Freedom

You can read more about how Robbie and I first met and our personal background on my about me page. Our transition to becoming a 100% self-employed family officially took place in March of 2017, just over two years into our marriage. The prospect was, quite frankly, terrifying. I vividly recall the physical nausea that gripped me when Robbie announced his decision to leave his part-time job. We were facing a myriad of responsibilities: an eight-month-old son, a mortgage, existing debt, and the relentless stream of daily living expenses. The weight of these commitments felt immense.

Life, undeniably, is expensive.

Venturing into self-employment is inherently daunting, but embarking on this path with a baby dependent on you magnifies that fear exponentially. The knowledge that a tiny human relies entirely on you for every single need, coupled with the desire to provide them with the best possible life, imposes a significant amount of stress. It’s a profound responsibility that can feel overwhelming.

But the ultimate reward? It was unequivocally worth every moment of trepidation.

The old adage “opposites attract” couldn’t ring truer for Robbie and me. He is a decade my senior, embodying a calm, composed, self-assured, optimistic, and laid-back demeanor. I, on the other hand, am a walking bundle of anxiety, perpetually grappling with self-confidence, a natural pessimist, and the antithesis of ‘chill.’ It’s amusing how life orchestrates such pairings!

Yet, our differences don’t create friction; they create balance. My inclination for business strategy, my affinity for numbers, and my ability to envision the bigger picture have been instrumental in helping Robbie grow his ventures. I built his website from the ground up, optimized his online presence to appear on Google, assist him in planning his schedule, help with job quoting, manage all our finances, and generally keep him organized. Where my pessimism might surface, his unwavering optimism and encouragement are always present. When I feel on the verge of giving up, he consistently assures me, with absolute confidence, that I possess the capability to succeed and that he is immensely proud of my efforts.

Even before our marriage, when we had known each other for only eight months, Robbie was a fervent advocate for my dreams. He encouraged me to chase my aspirations, and when I finally quit a job I detested just a week before our wedding, he was my most ardent cheerleader. This journey, I can confidently say, would have been impossible without our mutual support and unwavering belief in each other. Together, we are both living our dream careers, building a life that fills us with immense pride and satisfaction!

Making the Leap: Our Unconventional Path to Entrepreneurial Freedom

If you had asked me in February of 2017 about our long-term goals, I would have confidently stated that we aimed to be completely self-employed within five years. The very next month, we took the monumental leap. You can only imagine the whirlwind of emotions and the sheer intensity of that period for us!

As someone who inherently craves stability and safety, I often look back at my current life with a comical sense of disbelief. Robbie and I have always steered clear of conventional paths, so perhaps nothing should truly surprise me anymore! Each year brings radical change, and there’s no indication of that pace slowing down. Here’s a concise overview of our transformative years:

• 2014: Foundations and Beginnings
  This pivotal year saw our first date, engagement, and marriage. It was also the year I tentatively launched my blog, a venture that would later transform our lives.
• 2015: Growth and New Responsibilities
  Robbie transitioned to a new job, we proudly purchased our first home, and we discovered we were expecting our first child.
• 2016: Parenthood and Shifting Priorities
  Our son, Crosby, arrived, bringing immense joy and a new perspective. Shortly after my maternity leave concluded, I made the decision to leave my part-time, at-home job to focus more intently on my growing blog.
• 2017: The Defining Leap into Full Self-Employment
  This was the year Robbie resigned from his part-time position, marking our complete transition to self-employment. Remarkably, both of us managed to double our previous year’s income. Robbie’s lawn care business, in particular, saw an astounding five-fold increase in earnings compared to 2014.
• 2018: Strategic Growth and Sustainable Income
  We took a significant step by filing both our businesses as S Corporations. We successfully navigated another “landscaper’s winter,” primarily sustained by my blog’s income, which by this point had grown to a full-time income stream. I have a strong feeling this year will bring even more substantial achievements!

It truly feels surreal to reflect on where we were just three years ago. The pace of change and growth has been nothing short of extraordinary.

I often encounter individuals perpetually searching for the elusive “get rich quick” scheme. However, I must candidly state that such a thing simply does not exist. Many mistakenly perceive blogging as an easy path to rapid wealth, but it’s fundamentally like any other profession. It demanded years of dedicated learning, hands-on experience, honing skills, and relentless hard work to reach my current position.

I am a steadfast believer in the incredible advantages of self-employment. I strive never to take for granted the sheer privilege of having a job that, most of the time, doesn’t even feel like work.

I don’t just tolerate work; I crave it. My passion is so profound that taking a break often feels challenging.

I genuinely adore what I do. My biggest ongoing struggle is striking a harmonious work-life-mom balance. My desire to achieve more and work more is constant, yet my time is finite. This level of fulfillment didn’t manifest overnight. It took over three years of dedicated effort, which I believe is a reasonable timeframe to consider if you’re serious about pursuing a career rooted in passion.

Essential Guidance for Aspiring Entrepreneurs: Building Your Dream on Solid Ground

Build with a Safety Net: The Power of a Side Hustle

Resist the urge to prematurely quit your day job.

The allure of an immediate leap into full-time self-employment is strong, but it often leads to financial strain and burnout. In my experience, the wisest strategy is to cultivate your passion as a side hustle, dedicating every available moment to its growth. This approach significantly reduces the immense pressure of needing to pay bills, a relief that is particularly crucial if you have a family relying on your income.

Robbie, for example, maintained other jobs for the initial eight years of his business’s existence. Similarly, I worked a part-time, at-home job for over a year while diligently building my blog. This provided an invaluable opportunity to support my family, for which I remain profoundly grateful. The core takeaway is this: neither of us jumped into self-employment immediately, despite it being our ultimate aspiration. We built a foundation first.

Continuous Learning: Your Unending Competitive Edge

Embrace a lifelong commitment to learning.

Knowledge is unequivocally power. The more you absorb, the better equipped you become to assess whether your entrepreneurial aspirations truly align with your capabilities and passions. Even as a self-employed individual, the journey of learning never ceases. If you’re venturing into an unfamiliar domain, be prepared to invest the time in thorough research, hands-on application, and mastering the intricate nuances of your chosen field.

For me, even three years into my blogging career, I am perpetually seeking new knowledge and refining my skills. This relentless pursuit has allowed me to accumulate over three years’ worth of invaluable blogging expertise, spanning everything from the foundational principles of entrepreneurship to the intricacies of photography, WordPress development, SEO optimization, social media strategy, and much, much more. Never allow yourself to become complacent; always be on the lookout for new information and innovative approaches. If you find yourself doing the same tasks in the same way for an extended period, actively seek out fresh perspectives. More often than not, I discover there are always more effective strategies or untapped opportunities. The value of continuous learning truly cannot be overstated.

To further aid your journey, I’m delighted to share some of my favorite podcasts and books that have significantly influenced my path. If you have any outstanding recommendations, please don’t hesitate to share them! I am always eager to discover new sources of inspiration.

Recommended Resources: Fueling Your Entrepreneurial Spirit and Mindset

Awesome with Alison Podcast – This podcast holds a special place for me because it was the first one I listened to religiously, and it single-handedly transformed me into a podcast enthusiast. Alison’s style is a refreshing blend of humor, raw honesty, a touch of endearing eccentricity, and an abundance of genuine awesomeness. The podcast’s core mission is to elevate your sense of self-worth and capability, and I can attest that it has profoundly succeeded for me!

Last July marked a critical turning point for my business. I was experiencing a frustrating plateau, feeling stuck and unable to advance to the next level. Compounding this, I was battling depression and stress, all while caring for an 11-month-old son. My pride in my work was waning, and I questioned the future of my blog. I honestly wondered if I simply lacked the inherent drive or skill to elevate it further. Then, something within me shifted. I made a conscious decision to establish clear year-end goals for my business. The subsequent events were nothing short of life-changing. Not only did I gain a renewed sense of purpose, but I also committed to making my work a priority (a considerable challenge with a baby), and a surge of inspiration followed.

Many days would begin with a heavy mood, or I’d find myself in a sour disposition after a morning spent with a fussy baby, patiently awaiting naptime to finally focus on work. Motherhood, in its raw intensity, can be incredibly draining, often consuming every ounce of my energy. My go-to remedy during those unmotivated moments was to simply turn on the Awesome with Alison podcast. Incredibly, by the end of each episode, I would feel genuinely uplifted and my mindset would be completely transformed. Your mind is an extraordinarily powerful tool for success, and I’m still actively engaged in reshaping my thoughts and subconscious behaviors. I cannot recommend Alison enough for her incredibly encouraging words, not just to fellow entrepreneurs, but to anyone striving to become their best self. And yes, her husband Eric also features on the podcast, and he is equally fantastic!

Jon Acuff Books – Have you ever encountered an author whose writing resonates so deeply that you feel compelled to devour every single one of their books? That’s precisely how I felt about Jon Acuff. While on the hunt for insightful business books, I stumbled upon his work and was instantly captivated. His unique blend of humor and engaging writing style spoke to me profoundly. I absorbed his books as quickly as my schedule allowed.

Among his impressive collection, I would have to declare “Finish” as the most life-altering for me personally. That book is brimming with invaluable, golden advice. If you identify as a “serial starter” who struggles to complete projects, or if you simply wish to learn more effective strategies for accomplishing your goals, “Finish” is an absolutely phenomenal read. Here are some Amazon links to his books if you’re interested in exploring them. (Please note: if you make a purchase through my affiliate link, I will receive a small commission, at no additional cost to you.)

• Finish: Give Yourself the Gift of Done
• Start: Punch Fear in the Face, Escape Average & Do Work That Matters
• Do Over: Rescue Your Work, Your Career, and Your Life
• Quitter: Closing the Gap Between Your Day Job and Your Dream Job

One of his profound quotes from “Start” truly encapsulates his philosophy: “You don’t need to go back in time to be awesome; you just have to start right now. Regretting that you didn’t start earlier is a great distraction from moving on your dream today, and the reality is that today is earlier than tomorrow.” This quote serves as a powerful reminder that the present moment is always the best time to begin.

The Goal Digger Podcast / Jenna Kutcher – This resource is a relatively recent discovery for me, one I stumbled upon just a few months ago after another blogger’s recommendation. Jenna Kutcher is an accomplished photographer and entrepreneur who built a multi-million dollar online business before turning 30. Her down-to-earth and authentic personality shines through. While some episodes cater specifically to photographers, the podcast, overall, delivers an abundance of valuable and highly encouraging information for any entrepreneur. I also follow Jenna on Instagram, where she radiates positivity and body confidence. She possesses that rare quality of making you feel genuinely good just by listening to her, and she consistently inspires me on my journey of pursuing what I love. You can connect with her Goal Digger podcast Instagram here and her personal Instagram here.

Jen Sincero Books – Jen Sincero is another author whose work resonates deeply with me. I’ve read two of her books and am currently rereading them because of their profound impact. While her writing includes some strong language and certain concepts might initially seem unconventional to some, the overarching themes of self-love and breaking free from self-limiting thoughts are nothing short of phenomenal. I found myself utterly unable to put them down! Here are my Amazon affiliate links to her empowering books:

• You Are a Badass: How to Stop Doubting Your Greatness and Start Living an Awesome Life
• You Are a Badass at Making Money: Master the Mindset of Wealth

One of my favorite Jen Sincero quotes offers a potent challenge: “If you’re serious about changing your life, you’ll find a way. If you’re not, you’ll find an excuse.”

The War of Art by Steven Pressfield – This is another truly fantastic read, brimming with immensely practical advice, especially for creatives and anyone battling resistance in their work. Pressfield dissects the insidious nature of procrastination and self-sabotage, offering profound insights into overcoming these internal obstacles.

A few powerful quotes from this transformative book:

“Are you paralyzed with fear? That’s a good sign. Fear is good. Like self-doubt, fear is an indicator. Fear tells us what we have to do. Remember one rule of thumb: the more scared we are of a work or calling, the more sure we can be that we have to do it.” This quote reframes fear not as a deterrent, but as a compass pointing towards our true purpose.

“Our job in this life is not to shape ourselves into some ideal we imagine we ought to be, but to find out who we already are and become it.” A profound call to authenticity and self-discovery.

“The most important thing about art is to work. Nothing else matters except sitting down every day and trying.” A powerful reminder that consistent effort, not fleeting inspiration, is the cornerstone of creative and entrepreneurial success.

The Food Blogger Pro Podcast – This is an excellent podcast, not exclusively for food bloggers, but for any blogger seeking to grow their online presence. They feature interviews with a diverse array of interesting individuals, and I always look forward to their new episodes for fresh perspectives and actionable strategies.

The Theory of Content Podcast – This podcast is a relatively new addition to my listening rotation, focusing entirely on SEO. It features Joshua Unseth and Amber Bracegirdle, co-founder of my ad network, Mediavine. As I’m making a significant push to elevate my SEO game this year, I am thoroughly enjoying the depth and practical advice offered in this podcast.

If you have any book or podcast recommendations that have empowered your journey, please don’t hesitate to share them! I am perpetually on the hunt for compelling new content to listen to and read, fostering continuous personal and professional growth.

Lessons Learned: Advice for My Younger Entrepreneurial Self

Embrace Imperfection: Start Before You’re Ready

You don’t need to know the exact destination to begin the journey.

I believe this mindset often prevents many people from even starting to chase their dreams. We frequently convince ourselves that we require a perfectly clear, well-defined end goal before taking the first step. However, the reality of an entrepreneurial path is that the goal itself often evolves and refines along the way. When I first launched my blog, it bore a different (and, frankly, embarrassing) name, and my initial vision was to be a broad food and lifestyle blogger.

It took me a few years of consistent effort and self-reflection to truly grasp that my genuine passion lay predominantly in food blogging. While I still occasionally dabble in lifestyle content, my heart and soul are truly invested in developing and sharing recipes. Had I waited two years, striving for perfection before launching this blog, I would undoubtedly not be where I am today. There are quite a few older posts on this blog that make me cringe when I revisit them (everyone has to start somewhere with photography!), but the crucial lesson is that you simply cannot afford to wait until you’ve mastered everything before you begin. The act of starting is the true catalyst for improvement.

Undoubtedly, I am a vastly superior photographer and cook now than I was three and a half years ago. Like any skill, my abilities have dramatically improved through consistent, deliberate practice and countless hours of dedicated effort.

Cultivate Your Circle: The Importance of Support

Surround yourself with like-minded individuals who uplift and inspire.

When you make the brave decision to pursue a life divergent from the norm, you might encounter significant resistance or skepticism from people within your established circle. There’s a widely discussed psychological phenomenon at play here: when someone witnesses another person actively pursuing their dreams, it can sometimes trigger an unconscious urge to ridicule or discourage them. This reaction often stems from their own unfulfilled aspirations, a subconscious acknowledgment that they haven’t pursued what they truly desired. Other times, it’s simply an attempt to anchor you to the person they *think* you are, rather than empowering the person you *aspire* to be.

I used to roll my eyes at the notion that transforming your life begins with transforming your thoughts, but I now know, with absolute certainty, that it is 100% true.

If your immediate social circle lacks individuals who genuinely support your new identity and desired life path, actively seek out alternative sources of inspiration. Immerse yourself in as many empowering books and podcasts as you can access. As much as I wish I could magically leap through the screen to physically connect with inspiring entrepreneurs like Alison and Jenna, listening to their wisdom while I work provides an incredibly close second. A significant portion of the secret to entrepreneurial success lies firmly within your mindset.

Navigate Social Media Mindfully: Focus on Your Path

Minimize your time on social media platforms.

Easier said than done, wouldn’t you agree? My work necessitates a considerable amount of daily social media engagement, making it an unavoidable tool. That being said, the more time I spend idly scrolling through Facebook and Instagram feeds, the more I find myself feeling a sense of unease about myself and my own life. Social media is a cunning trap, designed to ensnare you in the detrimental cycle of comparing your life to the curated highlight reels of others. The most profound recommendation I can offer is to watch the Instagram stories of Colin Kartchner. His powerful message has completely reshaped my perspective on social media, even convincing me that my children will not be introduced to smartphones during their formative teenage years. I urge you to watch his content and allow your eyes to be opened to a healthier perspective.

If your ambition is to forge a new life and a new version of yourself, your focus must remain steadfastly on that goal, rather than being pulled back into the comfort of what is familiar. I refuse to remain the person I’ve always been; I aspire to so much more. I am already significantly different from the person most people in my life once knew. To truly transform your life, you must commit to transforming your habits and, fundamentally, your mindset.

Whenever I feel a wave of discouragement, my personal mantra is “eyes on your own paper.” I find myself at my happiest and most content when I am solely focused on self-improvement and cherishing my family, rather than falling into the trap of comparing my life and successes to strangers or acquaintances encountered on the internet.

Conquer Perfectionism: Action Over Idealism

Do not allow perfectionism to paralyze your progress.

Ah, perfectionism, my old nemesis. For entrepreneurs, perfectionism is an insidious toxin, a silent killer of dreams and progress. Its most significant impact on me was the years I spent struggling intensely with my food photography. If a picture wasn’t ‘good enough,’ I simply wouldn’t post the recipe. If I could turn back time, I would shake my past self and emphatically tell her to post it anyway. Nothing in life or business will ever achieve 100% perfection, and by waiting for an unattainable ideal, you only succeed in holding yourself back. Don’t delay publishing that recipe or launching that website. Just do it.

I find immense wisdom in this quote from Jon Acuff: “90 percent perfect and shared with the world always changes more lives than 100 percent perfect and stuck in your head.” This powerfully reminds us that impact comes from action, not from endless, internal refinement.

The Reality of Self-Employment: The Perks and Pitfalls of Entrepreneurial Life

Before concluding, I want to take a moment to truly appreciate the incredible privilege of working for yourself. Here are some of my most cherished advantages of the life my husband and I have painstakingly built:

The Rewards of Building Your Own Empire

• Love for Our Work: We genuinely love what we do. Our jobs are extensions of our passions, making work feel less like a chore and more like a calling.
• Anticipation, Not Dread: We eagerly anticipate starting our workday, rather than dreading the Monday morning grind.
• Flexible Schedules: I have someone care for Crosby at home approximately 15 hours a week, allowing focused work time. Otherwise, I can structure my hours around nap times, evenings, or weekends, providing unparalleled flexibility.
• Constant Presence for Family: I am consistently able to be at home with Crosby, never missing precious moments of his development.
• Weather-Proof Family Time: Rainy or snowy days, which often halt Robbie’s landscaping work, mean he’s home to play with Crosby, while I can often get extra work done during these unexpected ‘indoor’ days.
• Seasonal Downtime: During the winter months, Robbie is home approximately 90% of the time, as landscaping work slows significantly. This allows for extended family time without needing vacation approvals.
• Freedom to Travel: We can embark on vacations for weeks during holidays, like Christmas, without the need to seek permission from a boss or worry about limited PTO.
• Passive Income Streams: I can take a day off work and still generate significant income. The power of passive income is a game-changer for financial stability and freedom!

That being said, it is crucial to acknowledge that being self-employed is undeniably hard. Here are some of the ways our lives have become more challenging since making the leap:

Navigating the Challenges: The Hard Truths

• The Myth of “Off Hours”: For Robbie, this often translates to returning client calls and preparing quotes after he’s arrived home from a full day’s work. Some nights, it’s 9 p.m., Crosby is finally asleep, and we’re just sitting down to meticulously plan his schedule, respond to client emails, and diligently track the business finances. For my blogging career, it means I almost never truly take a day off. There is an inexhaustible list of tasks that never seem to be fully completed when you run an active blog. I frequently work late nights and weekends, and I actively struggle with being fully present because my mind is constantly preoccupied with the myriad of uncompleted tasks. This is a challenge I am acutely aware of and consciously working to improve. While I deeply love my job, I am resolute that my son will not grow up feeling that I prioritized work over him. He will always, always be my most important priority.
• The Real Cost of Living: When you’re self-employed, the financial responsibilities extend far beyond just earning money. Not only are you solely responsible for your own health insurance premiums, but you also bear the full burden of retirement planning, all business expenses, additional self-employment taxes, estimated tax payments, and the extensive list of costs associated with operating your own venture.
• The Tax Labyrinth: This brings me to arguably our biggest struggle: taxes. The complexities of taxes and the accounting side of self-employment are enough to make any sane person want to retreat. This has, by far, been our most significant hurdle, despite my having studied business and accounting in college! My sincerest advice is to hire a competent accountant as soon as you reach a point where your business is generating a full-time income or when you’re ready to scale to the next level. We finally made this crucial decision in March, and the reduction in my workload has been nothing short of immense. However, even with an accountant, there remains a substantial amount of financial oversight required for running two businesses. It is most certainly not for the faint of heart! This year, we also strategically transitioned both our businesses to S Corporations and implemented payroll services through our accountants, processing our own salaries from our company accounts. While the initial setup was a considerable headache, we anticipate this will significantly simplify our financial lives moving forward.
• The Weight of Responsibility: You are entirely responsible for your own earnings. It is an inherently scary prospect to depend solely on yourselves for income. If a week of incessant rain occurs, Robbie’s income is directly impacted. If it’s a slow period for advertising, my blog’s earnings naturally decrease. While this aspect is also a perk, offering the potential to earn far more than a salaried position, it simultaneously carries the immense pressure of consistently generating enough income to provide for your family’s needs.

That was quite an extensive discussion, and if you’ve made it to the very end of this post, I extend my heartfelt gratitude for reading along!

I genuinely believe that if more individuals pursued work they truly loved, the world would undoubtedly be a happier and more fulfilling place. Perhaps your aspiration is to transition to full-time self-employment, or maybe you simply need to dedicate more time to activities that bring you joy outside of your current job. Whatever your situation, my sincere hope is that this post has ignited within you a desire for more – a desire to create a life that truly resonates with your deepest self. I steadfastly believe in the transformative power of each person making a conscious effort to love themselves more deeply and to continually strive to become the best possible version of themselves they can be.

“You are perfect. To think anything less is as pointless as a river thinking that it’s got too many curves or that it moves too slowly or that its rapids are too rapid. Says who? You’re on a journey with no defined beginning, middle or end. There are no wrong twists and turns. There is just being. And your job is to be as you as you can be. This is why you’re here. To shy away from who you truly are would leave the world you-less. You are the only you there is and ever will be. I repeat, you are the only you there is and ever will be. Do not deny the world its one and only chance to bask in your brilliance.” – Jen Sincero

Explore More of Our Food Blogging Journey: Related Posts

• 20 Essential Lessons from My First Year of Food Blogging
• Two-Year Recap: Celebrating Our Blogging Milestones
• Three Years Strong: Reflections on Our Entrepreneurial Growth
• Five Years In: My Evolving Career as a Food Blogger