Ten years ago, I made the difficult decision to leave my 10-year corporate marketing career behind to start my own business. At the time, I was working for a well-known, global consumer ice cream brand at an established, international company. However, my growing disillusion from my job focused on increasing ice cream consumption, combined with my interest in professional coaching followed by my father’s death, led me to leave that stable life behind to start my own independent consultancy focused on helping people navigate career transitions.
Aside from hiring a few freelancers to help me with specific targeted tasks, I’ve been flying solo since, and this chapter of my career has been one of the most eye-opening. Self-employment can be intense, frustrating, and tiring at times while also being rewarding, gratifying, and enriching.
Over the past decade, I’ve learned so much about myself, the role work plays in life, and the importance of honoring your personal and professional priorities. These 10 lessons stand out as some of the most important:
1. Every Experience Is A Learning Opportunity
Looking back on my former life as a full-time corporate employee, I now realize I existed in a bit of a bubble of carefully curated professional training, events, environments, and teams, which I’ll admit is a privilege I miss at times. Large companies offer relatively easy, regular access to top-tier training and formalized skills development.
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One of my concerns after leaving my corporate job was potentially falling behind my peers or losing my professional edge. Especially during the early days of self-employment, I didn’t exactly have a huge training budget or access to the same caliber of training. The quality of offerings and experiences varied wildly, and I had plenty of experiences during self-employment that completely missed the mark. Still, I found each taught me something.
For example, at a free business owner’s training event I joined in London hosted by someone who bordered on seeming like a fraud in the end, I still learned useful lessons about stage confidence. Another example involved hiring a freelancer who misrepresented her skills to me, which taught me how to more diligently vet people before hiring them. I also had my fair share of client engagements that didn’t go as planned, so I learned how to more precisely evaluate potential projects. I’ve also turned to many nimble digital tools outside of the traditional Microsoft Office Suite of products to run my business, which has opened up a whole new way of working for me.
With the right attitude, the personal and professional growth you can experience while self-employed can be tremendous not despite but because of the volatile nature of running your own business.
2. With Pricing, Fairness Is King
Pricing has always been one of the trickiest things for me to figure out as a business owner. Even after 10 years as a service provider, I still struggle with where to set my fees. You don’t want to set them too low and undersell yourself. However, you also don’t want to set them so high that you price yourself out of the market.
I’ve been told by most clients that I certainly don’t charge little for my services, but I’ve also had plenty of friends and family tell me I could still charge more. As a former marketer myself, I do understand the concept of a product or service being worth whatever someone’s willing to pay. I’m aware that setting prices high signals a certain positioning, so I’ve always erred on the side of setting higher fees rather than lower fees to not only signal the quality of my services but also force me to bring my A-game.
At the same time, I’ve been very careful to avoid being greedy. Fairness is a key value of mine, so when setting my pricing, I always ask myself whether I feel my rates are fair to both me and my clients based on each of our respective situations. And yes, it’s a tough balancing act I have yet to figure out.
When in doubt about where to set your pricing, remember that fairness is your best compass.
3. Discipline Trumps Talent
I’ve met a lot of talented people over the years. Some are extremely good with numbers. Others are very charismatic, impressively articulate, or extremely efficient. Still others have attended Ivy League schools or worked in high-profile positions with an impressive list of top-tier companies on their resumes.
I would never describe myself as the most talented or accomplished person in any room, especially when it comes to running my own business. I’ve had plenty of missteps and oversights over the years. And I’d say that few things have come naturally to me as a business owner.
However, one of the reasons why I feel my business has steadily grown over the years is due to my sheer grit and determination to put in a steady, consistent, and meaningful dose of effort every single day. While I’m nowhere close to being the smartest guy out there, I would consider myself very disciplined as a self-employed business owner. While I do take breaks, I rarely slack off. While I enjoy the flexibility of self-employment, I stick with my self-imposed deadlines. And while I set my own work hours, I am 100% focused on my tasks at hand during those hours.
In the world of self-employment, skills, talent, and training are not enough. Above all else, you need commitment and consistency for your business to survive and thrive.
4. Progress Takes Longer Than You Think
In all my years of self-employment, everything has taken more time than I imagined. My newsletter subscribers grew more slowly than I thought. Student enrollment into my online courses took longer than I expected. My social media followers climbed more slowly than I hoped. My podcast’s listenership took years not months to reach an audience figure that I considered significant. My salary took longer than I wanted to reach and eventually exceed my former corporate salary.
Because of this, I’ve tried to let go of success metrics related to time. Most things take longer than you expect, especially when you’re working on your own. At a very micro level, with no broader team, you often get less done than you hope each day because you have to deal with every single issue that pops up. Whether your website is not working as expected or an invoice hasn’t been paid correctly or your computer stops working, the onus is on you to address it. And at a more macro level, when you don’t have backing and resources of a larger company, you’re limited in what you can accomplish on your own.
Being realistic about what you reasonably achieve within a certain time can help you maintain a positive business outlook, even if you’re not gaining the traction you want as quickly as you want.
5. Things Can Always Be Better. . . And Worse
Especially in the first few years of self-employment, I often fell into the trap of feeling like my business wasn’t growing as fast as I wanted. I sometimes wished I had a bigger following. Or my podcast had a higher listenership. Or my online courses had larger enrollment. Or at least one of my articles went viral (for the record, I’m still waiting for this to happen).
Beating yourself up over not achieving as much as you wanted to as quickly as you envisioned is all too easy, especially when your comparison set includes people in the popular press who seemed to be crushing it.
Whenever I’ve felt down about some aspect of my work, my progress, or my growth, I’ve always tried to remind myself that while things could always be better, they could always be worse. I’m doing okay in the big scheme of things. I have accomplished plenty, and while the aspirational side of me always yearns for more, I’ve learned to be okay with less.
Taking stock of all you have accomplished can enable you to enjoy the journey a bit more and appreciate what you have rather than obsess over what you don’t have.
6. Every Business Choice Involves Tradeoffs
Few decisions I’ve made when self-employed have fallen into the category of being universally right or wrong. Instead, I’ve made choices that have served the business and life I’m trying to create. Sometimes other coaches ask me why I’ve chosen not to grow my team. Friends have asked why I don’t allow ads on my podcast. Followers sometimes ask me why I didn’t end up writing that book I said I would. Others ask me why I don’t outsource more business tasks than I currently do.
Any business choice involves trade-offs. Choosing to remain solo and not hire employees has meant I’ve had to turn down client work, especially recently, but I’ve managed to retain the autonomy I wanted from self-employment. Not having paid advertisem*nts on my podcast has meant the show doesn’t generate direct revenue, but it means listeners can hear these career-change stories without unhelpful distractions. Not writing that book was a missed opportunity, but it meant I could be present with my daughter when schools were closed during the pandemic. And not outsourcing tasks like invoicing, presentation creation, or content marketing has created a bottleneck in how much I can do on any given day, but it also provides me with total control over client-facing interactions to shape my reputation more precisely in a way that has served my business well.
If you ever find yourself struggling to decipher what’s “right” for your business, just remember that it depends on what you want for yourself, your clients, and the people in your life.
7. Benefits Come In Many Forms
One of the things I struggled with when walking away from my corporate marketing jobs was letting go of the cushy perks that come with working for a large company—benefits, retirement packages, a nice office, unlimited coffee, free food . . . even small things like office supplies.
While I don’t say no when someone invites me along to a cushy corporate party at a fancy location with a nice dinner, I’ve come to value other luxuries that come with self-employment. I love being able to control my schedule. I like being able to freely express my opinions and design my presentations without having to adhere to corporate templates or talking points. I enjoy spending school holidays with my family without having to count vacation days. I value having the freedom to choose which client engagements to take on. I enjoy being a very present father during my daughter’s childhood years. And I love doing work that I find truly meaningful, purposeful, and fulfilling.
Luxury is often associated with material assets. However, freedom, autonomy, and control are truly priceless.
8. Yes, Self-Employment Can Be Financially Lucrative
Money was nowhere close to being one of my primary motivations for pursuing self-employment. Freedom, autonomy, flexibility, and doing work that I found more meaningful were at the top. However, with that said, if you’re doing work you love, you can also earn a comfortable living doing it.
Yes, I ran a very lean, low-budget operation during the early days of running my own business when my income was far beneath what I used to earn in my global marketing job. We initially downsized our home, and I drastically reduced all discretionary spending in my life. I did and still do watch my budget.
While it didn’t happen overnight, my income slowly returned to and eventually exceeded my former salary. I now sometimes earn more on a single day than I earned in a month in the corporate world. I now sometimes earn more in one month than what used to earn in a year. And yet, while I can now say this, I also don’t assume I have it all figured out.
I continue to give 100% to my business every day because I know, as the pandemic proved, that things can change on a dime. Nothing is forever. Any business, including mine, is delicate at best. Clients are much easier to lose than gain. I’m not immune to things beyond my control that can send my business into a downward spiral. Because of this, I never get too co*cky about anything I’ve achieved because it doesn’t take much to get knocked off course.
Yes, you can earn a comfortable living when self-employed. However, as is the case with any small business, you’re only ever a couple of sudden twists or turns away from things changing quickly, so I never take anything for granted.
9. Controlling Your Own Destiny Is A Form Of Stability
I used to think a full-time corporate job offered more professional stability and job security than self-employment. A sense of comfort comes with having a regular pay check, employee benefits, and the safety net of a large, established company that’s been around for decades. In contrast, self-employment can feel less predictable, where your income can fluctuate wildly as you try to secure work, maintain a steady stream of clients or customers, and arrange your own health and retirement benefits.
However, stability means different things to different people. Yes, the common belief is that full-time employment at a company can provide a sense of certainty and predictability. However, sudden company reorganizations, budget cuts, or rounds of layoffs similar to those we’ve all seen in the news recently demonstrate how full-time employment isn’t immune to unpleasant volatility.
I’ve experienced unexpected setbacks while running my own business like all my paid speaking engagements get canceled during Covid or a client canceling a project. However, in these situations, I had complete agency and authority to change course, diversify my income streams, or reshape my service offerings.
Self-employment is not without risk. At the same time, I find it comforting that I’m not at the mercy of an employer to control my destiny.
10. Running Your Own Business Is A True Privilege
Not everyone has the latitude or life circ*mstances that enable them to leap into the world of self-employment. Make no mistake, attempting to start your own business involves risk, financial uncertainty, and even loneliness as you balance all the responsibilities of doing everything by yourself, especially during the early days.
However, self-employment also offers many benefits like having a sense of purpose, controlling your work, setting your schedule, removing limits on your earning potential, or turning your interests into your livelihood. Building a business around something you love doing can create a sense of fulfillment and purpose.
I’ll admit, I feel busier and more alone now compared to my days as a corporate employee. I’ve gone through some volatile periods over the past 10 years that have certainly kept me up at night or madly scramble during the day. But overall, I feel much less stressed and more at peace with my work life, especially because I’ve built a business that aligns with the person I want to be and the family life I want to have. I just feel healthier, both physically and emotionally.
I’m sometimes hard on myself whenever things don’t go my way in my business. But I always try to remind myself to stop every so often and acknowledge how far I’ve come. To appreciate the benefits self-employment offers. And to always be grateful for having this opportunity to make my unique mark in a way that continues to energize me every single day.
