Building a Business: 5 Surprising Things I’d Tell My 20’s Self

It’s hard to imagine that almost five years ago, I had graduated college into the lowest point of my life. I was saddled with heavy student loan debt, medical bills, and was earning only a modest entry-level salary that could barely keep me afloat. After graduating college and high school at the top of my class, working hard to develop highly marketable skillsets, and spending years becoming the best that I could be, I thought I had failed. I had no idea how to move on from the decision to attend an expensive school and major in a non-technical field.

Flash forward five years: I’m running my own content marketing business and feeling like a success. I wish I could go back in time to tell my down-in-the-dumps self that everything would be okay. I also wish I could go back and tell that same person the five key lessons I learned along the way from feeling like a failure to feeling like a success. I think that would have made the journey a lot less painful, and perhaps might have sped things up.

Lesson #1: Chase experience, not the salary

As much as I loved my full-time job as a marketer, it wasn’t enough for me to pay the bills. So I started freelancing: partly for fun—to take my mind off the soul-crushing financial stress that was eating me alive and partly out of necessity—to empower myself with a little more financial stability. I was 23 years old when I landed my first freelancing client. I found the gig on Craigslist and was thrilled to be making $8 a post.

Little did I know that walking through this door would completely change the direction of my career.  I felt a new sense of empowerment and passion for the field of online marketing and leveraged my freelancing projects to gain new skills—and build a reputation—in my field.  The more I learned about online marketing, data, and analytics, the more I was able to increase my value as a consultant and content creator.

If I knew then what I know now, I would have spent less time hounding down opportunities for income. I would have spent more time investing in my own personal brand—even taking on unpaid writing opportunities to boost my portfolio. I would have spent more time enjoying the moment.

Lesson #2: A side business is the ultimate career investment

My freelancing venture empowered me to become an even better employee. Everything I learned while writing, I would directly apply to my full-time role.  The more my freelance business grew, the less I felt like I ‘needed’ my full-time job to stay afloat. I went to work because I wanted to be there.

That agility, positive attitude, and passion for the work landed me three promotions—which more than doubled my salary level—in four years.  I remember the first time I was promoted in June of 2011. My boss surprised me with a very generous raise. I was finally financially stable. Moments after, I walked into the bathroom, put my head in my hands, and cried tears of joy.

People always advised me to keep my side business a secret from my employer. I chose not to do so, especially since my work is so public-facing. Instead, I made an active effort to position my work as a supplement to my full-time role. I walked the talk and always looked for ways to be better in my full-time job. Looking back on my decision to be transparent, I am very glad that I did. My bosses always supported me and always perceived my ventures as a contribution to my full-time role.

I do wish, however, that I had done more to integrate my full-time job and my side business even more. I was sometimes afraid to share experiences or even tell some of my colleagues how I came across a business contact or idea. I wonder if I would have been able to push my career growth further.

Lesson #3: Dreams are worth more than money

In November 2013, my freelance income overtook my full-time salary. Push had come to shove, and I was at a point where I needed to make the choice between running my own business and being an employee. Many people would consider this to be a happy moment, but I was terrified. The fact is that I loved being an employee and part of a team. While my dream was to become an entrepreneur ‘one day,’ I was not ready for that day to be now.

What ultimately pushed me to make the jump was my dad—someone who I considered to be very risk averse. I expected him to tell me that I was crazy, with my head in the clouds. But he didn’t. He told me, “If there’s one thing in my life that I would go back and re-do, it would have been taking the opportunity to take a jump like you can now.”

At that point, I knew I had to do it. I stopped thinking with my heart and listened to my head. Even with my student loan debt, I didn’t care about the money—what I wanted most was to make a positive and tangible impact on the world. I realized that to achieve this goal, I would need to take the jump and become an entrepreneur. So I did it. I pursued my dream, fully aware that the months ahead would come with many ups and downs. And at the end of the day? I don’t care how much money I’m making. What inspires me is that I’m creating.

Even though I’m only three months into my journey, I haven’t looked back. Of course, I have days where I am very stressed about the uncertainty, but I’m realizing more and more that this emotional response is something that I have to learn how to control. I am learning how to tackle my biggest weakness—fear of risk—and I know that this milestone will be worth just as much as any successful business that I am able to build.

Lesson #4:  Anything can be a business

I meet so many college grads who feel that they need to give up their childhood dreams for spreadsheet-bound paths. What I’ve learned, however, is that these trajectories are far from mutually exclusive. As a content creator, I use spreadsheets every day and frequently rely on skills from my statistics-based master’s program.

The key to making your hobby your business is to find where your passions align with the market. Think about how you can translate your activities into a clear and compelling revenue model.

And if business isn’t your area of expertise? That’s completely fine. There are advisors, mentors, or coaches to help provide direction.

I wish that I had reached out to an expert sooner. My younger self had always perceived the world in black and white terms—writers are broke while investment bankers are wealthy. Had I consulted someone who had ‘been there before me,’ I would have quickly learned that it’s entirely possible to transform my hobby into a revenue-generating business.

Now, I have reached a point where I see the world through entrepreneur-colored glasses. It’s addictive. Anything and everything can become a business. The art is in the plan and execution.

Lesson #5: ‘Someday’ Is now

This is a lesson that I should probably also tell my late-20s self.  I have spent the last 3 years of my life working my tail off—sometimes 12 to 15 hour days. You might think I’m bragging, but I’m not. I’m not proud of it. I sacrifice social engagements for work and am constantly exhausted. I make the excuse that ‘someday’ will come and life will ease up, but I’m beginning to realize that it won’t. It didn’t when my business was a side business, and it certainly hasn’t now that my company, Elate, is a full-time thing. It’s the same quandary that I went through when deciding to take the jump. I waited so long for ‘someday,’ but the reality is that ‘someday’ is right now. The work will never stop, but life will continue to pass by.

Realistically, I probably could have arrived at where I am now without having lost so much sleep. I would have been just fine with a few extra hours of relaxation. Even now, this realization is a struggle for me. But I’m starting small and experimenting with more ‘hacks’ for work/life balance. I am taking more walks, enjoying a lunch break, and taking nights out with my friends and family. The ultimate reality is that my work is never going to stop. But life is so much more than what I do—it’s who I am.

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