Opening a business is one of the most challenging, fulfilling, and nerve-wracking things I’ve ever done. I worked as a banker (“financial services representative,” was my fancy official job title) in a credit union for almost five years before suddenly finding myself job-less. Since I was a bit put off by the monotony of having an 8 to 5 day job and I had a decent amount of savings stock-piled away (read: enough to support myself for several months despite making some bone-headed business decisions), I decided to pursue self-employment as a blogger and personal trainer.
1. My first paying client (pro: nothing boosts confidence like helping a person change their life).
The scariest thing about working from home is not having a set income; even worse, it is just plain petrifying to actively seek your first paying client. In a typical sales job, you’ll be provided with scripts that help you communicate effectively, financial incentives that motivate you to deliver, and managers to keep you accountable; but if you’re a freelancer working from home, you’re the only one with the power to make the sale. I’ll never forget how happy and excited I was when I got a message from a friend that said something like, “Hey! I’ve been loving these fitness and motivation tips you’ve been posting on Facebook, and I know you’re training people now, right? Let me know how to sign-up, because I’m ready to make some changes!” That single client, a busy mom who ended up losing quite a bit of weight and developing a whole lot of strength, became a cheerleader who not only encouraged me to keep going, but also attracted the attention of more people who became clients in the future.
2. The devastating break-up (con: don’t expect everyone to support you, especially if you get obsessed).
When I first started a business, I became so consumed with wanting it to be successful that it was all I could think about. Add in the fact that I have an addictive personality (get obsessed with things very easily), and you can see how this might have spelled trouble for my relationship. My ex-girlfriend quickly became exhausted by how I never talked about anything but business stuff, and we ended up having several nasty fights about it. I was upset, because she seemed to be disinterested in what I was passionate about, and I accused her of not being supportive. She was upset, because I seemed to be disinterested in our relationship, and she accused me of being self-centered. I don’t think either one of us was completely “right” or “wrong.” I think she could have been more understanding and patient with me, since my life had radically changed in a short period of time; but I also could have been more considerate of her feelings, since a relationship can’t flourish without proper care and attention.
3. My smash-hit Kindle release (pro: if you hustle consistently, you will be rewarded for your effort).
4. The bout of depression that followed (con: you better not get cocky, because success doesn’t happen overnight; it is an every day struggle).
The point of that Kindle release (other than helping people like you get fit and fabulous, of course!) was to direct traffic to a sign-up page for my online coaching program. Since I was selling the book for 99 cents at the time (it is now $2.99, but also better), I didn’t expect to get rich from it. I thought I might be able to get enough readers interested in my paid service to become financially stable. While I did pick up a few clients, the actual result didn’t come close to mirroring the expectations I had set for myself, and I found myself in the middle of an existential crisis where I wondered if there was any reason to bother trying anymore.
5. My first paid writing gig at Lifehack (pro: it’s nice to have freedom to express yourself and create your own schedule).
If nothing else, reader reviews of my Kindle book boosted my confidence as a writer, so I started looking for paid writing positions that might offer a steady income stream, which I hoped would remove the stress of not being sure I would have enough clients to cover my bills. Lifehack was the first place to take a chance on me. I am very thankful for that, because they gave me a creative outlet where I was free to express my fears, frustrations, and feelings in a way that would benefit people like you (yeah, you, over there reading this!). Contributing for Lifehack has also resulted in getting offers to write for other places like the Motivation Alliance, an online health portal and gamified fitness tracking service for corporate wellness plan participants. Now that I have a decent portfolio and track record built-up, I’m hopeful that I’ll be able to find more fun writing gigs just like these as long as I’m persistent about it.
6. The lonely days that dominated my life for half a year (con: you will get lonely if you’re used to working with other people).
The “freedom” I discussed above can quickly turn into loneliness if you’re not careful. Remember how I mentioned that I have an addictive personality? I got so consumed in writing Lifehack articles, personal blogs, and my first print book* that my social life (and sanity) suffered as a consequence. I love to hustle, and can keep going and going like the Energizer Bunny for a very long time (months!), but pushing myself too hard for too long inevitably leads to a depressing place where I start to associate work with misery. I was so used to working for hours without end that visiting my family, going on a hike, or enjoying a few drinks with friends started to feel like frivolous things to do. Eventually, the irony dawned on me: I wanted to make enough money through my writing and coaching to have freedom of time, yet I was acting as if I was so chained to my work that I couldn’t even escape for a brief moment to get away from it all. *This isn’t released yet; if you want to know when it is, please check out the links in my bio at the end of this article.
7. My “let’s meet in the middle” compromise (pro: you can pursue a part-time gig if you start to miss people and/or could use some extra income).
Given my loneliness (which I feel was a direct consequence of living and working alone for over two years) and the simple fact that some extra income would remove a lot of the pressure I had placed on myself, I started browsing job ads in my area. I hoped to find a gig that didn’t quite demand a full 40-hour work-week, because then I’d still have plenty of time to coach, write, and work on my own business. My search concluded in me accepting a position as an office manager at an area YMCA, which only requires about 30 hours a week (and combines fitness and business, two fields I take a great interest in). It amazes me how working with other people, something I took for granted in the past, all of a sudden felt like a welcome escape from the lonely days I’d grown so accustomed to.
8. The woulda, coulda, shoulda’s (con: you will make some bad decisions you wish you could reverse, no matter what you do).
No matter how hard you try, you will fall short. No matter how much you plan, you will make mistakes. No matter how hopeful you feel, you will experience disappointment. I don’t say these things to discourage you from pursuing self-employment. I say it to prepare you for a harsh reality that a lot of people like to pretend doesn’t exist. I’m happy I pursued my passion, but I wish I could reverse some of my decisions. I know I can’t hop in a time-machine to change the past and make all my problems go away, but I can reflect about it here, which might be helpful for you. Below are the four biggest things I would have done differently.
- I would have made more time for my friends and family instead of obsessing about work so much. You do have to say “no” sometimes so you can get things done, but that doesn’t mean you have to become a hermit like I did.
- I would have kept a part-time job initially instead of diving straight into it, because that would have helped me save money I could invest back into the business (and I might have even avoided those lonely days).
- I wouldn’t have waited so long to start pursuing freelance writing jobs. I love to write (so much that I’d do it for free), but I think I could have been getting paid for it a lot sooner than I did.
Make sure you weigh the pros and cons of working from home before pursuing self-employment. If you have any points you’d add to this list or stories you’d like to share, do so in the comments. Please share with anyone you feel would be helped by it.
Featured photo credit: Woman and young girl in kitchen with laptop and paperwork smiling/GSCSNJ via flickr.com
