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What I Wish I Knew In The First Year of Going Solo


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In spring of 2011, I teetered toward the final days of a company in which I had placed nearly 3 years of my life. My decision to leave the company was not out of spite. On the contrary, my boss (and colleagues) encouraged me to move on. The direction I was heading was a full-time position playing the role of a freelance writer.

I had already set in motion a series of events that were going to ease the transition. The year prior to my departure had me spending countless hours endlessly toiling with website creation, marketing, and networking. I was putting in nearly 12 – 16 hours of work each day and the only reason I didn’t do more was that I had to sleep.

My efforts paid off.

The day I left the company to start my freelance writing business, I created several streams of income from the success of websites I had been working on. I was earning around $1,500 a month from the sites, if I remember correctly, which was more than enough to cover the essentials.

However, I still had that employee mindset.

I was adjusted to the comfort of the job. I knew I would receive a paycheck as long as I showed up and did the required work. I had limited freedoms for choosing my daily tasks and there was always a backlog of items to complete.

Stuck in this mindset, the first few months of going solo turned out to be a real pain in the rear.

It quickly became apparent that most of my work wasn’t about doing the actual writing but taking the time to network and discover clients. The first few months, I spent about 80% of that time sending inquiries to small businesses and website owners.

Luckily, I had income from the website, but that was soon to change …

There came a shift when I finally landed clients. Time management was essential; otherwise I wouldn’t have the ability to deliver work on time. It was equally important due to the balancing act of operating the websites while faced with upcoming deadlines.

The time division resulted in a drop in income from my websites. Earnings from clients weren’t covering the difference. I knuckled down and did more than ever. I’m glad to say that my freelance writing venture has flourished since I made the leap to go solo, but I can’t help to think how things would have been different if I knew some of the pitfalls awaiting me around every corner.

What I Wish I Knew

I have to admit that the first year of full-time freelancing was an absolute blast. Even though I made plenty of mistakes, I couldn’t stop smiling because there I was out on my own, for the first time, without having to report to a boss.

With that being said …

There were plenty of mistakes I made:

Billing (and finance) is a real hassle

The panic that sets in when a client decides to push back paying an invoice a week or flat-out bails on their obligations will give you a mini heart attack. There are times when you’re just days from folding because of an unexpected event and there’s no safety net to catch you like you had before.

Invoicing is manageable as long as you keep on top of things. This may include frequent reminders to clients that an invoice is past-due. You may need to rewrite your invoicing to improve its effectiveness.

The big wakeup call for me was the fact that I wasn’t keeping track of my financial records as well as I had hoped. That first year of doing taxes turned into quite a hefty payment to the government since I wasn’t taking out enough for Medicare and the like.

Bootstrapping can only go so far

Being young and well-adjusted to the Web has its perks. I’ve spent enough time online that I know my way around Web technologies in order to get an online business up and running. This is good in the beginning if you’re trying to bootstrap, but after a while you hit a glass ceiling. There’s only so much you can do with limited funds and I’m still kicking myself for not soliciting outside investment, whether that’s trying to gain awareness from a VC or just some funds from family or friends.

What I should have done is set aside more money from when I was working full-time at the job. I should have also researched accounts receivable financing. A small loan would have been perfect in the beginning and saved me a ton of time constantly trying to solicit clients and advertise the business (especially when trying to do so by bootstrapping).

Sometimes the “eggs in one basket” is the better choice

I know we all like to say “don’t put your eggs in one basket” but now I’m thinking that the opposite may be true. You see, when you hop into going solo you don’t have to report to anyone so you’re likely to branch into all kinds of opportunities. You’ll read about some strategy and disregard important work because you’re excited to give it a try. You start projects on a whim because they’ve been on your list instead of hunkering down and refining your skills.

I can’t begin to tell you how many websites and side ventures I created in that first year which are now extinct.

I look back and realize that I put way too much time into these side projects. I wanted to diversify my income so much that it was hampering my ability to specialize. I wish I had put 100% into one focus and seen it through to its end versus giving a fraction and trying to do it all.

In the end, things worked out. I made a ton of mistakes in that first year that I’m quite happy to have experienced. It’s given me the knowledge of what I can expect if I repeat them again. I hope you found this story interesting and thought-provoking. Get out there and do your best!

Kevin is an account director at Online Rep Management and has been working within internet marketing and public relations for over 8 years. Kevin got his start working online in SEO, link building, and some affiliate marketing. Kevin is most passionate about helping good brands become online entities. 

Reprinted by permission.

Image credit: CC by adib.wahab

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About the author: Under30CEO

Under30CEO is the leading media property for entrepreneurs, inspiring the world’s next generation of business leaders. Under30CEO features direct interviews with the most successful young people on the planet, profiles twenty-something startups, provides advice from those who have done it before, and publishes cutting edge news for the young entrepreneur.

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