When should you make the leap?

In each of these articles, I will consider one example of someone who changed careers and discuss what they think they did correctly (and, of course, incorrectly). However, if you haven’t read the first article I wrote, entitled Five Questions to Ask Yourself, I encourage you to read that before you start on this one. This week, I am going after the low-hanging fruit – my own career change. I started working in venture capital right out of college in 2000. I worked for a fairly successful firm, and I was one of the top junior professionals within the firm. While I worked very long hours, I enjoyed most of what I did. I was able to travel regularly throughout the U.S., and I even managed to spend the better part of a year living on a beach in Southern California, which is about as close to my dream lifestyle as I could come. While my life was going very well, the same could not be said for my firm. While I was living in California, the firm downsized dramatically, and by the time I was called back to New York, virtually everyone at the company had either been let go or was about to be. In the face of this turmoil, I turned to the thing that had always comforted me: writing stories about the people around me. When your environment is crumbling around you, sometimes it is hard to stay positive. I am the first to admit that, after 3+ years of stellar performance, I lost my desire to work for that firm. So I left, with the idea that I would write a novel and be a famous author within a year. It is three years later now, and while I have written a few books (and I continue to write every day), I am not making a living off of it. I have gone way into my savings, and I have taken several consulting assignments that I wish I had avoided to pay some of my bills. My essential problem is this: I love writing, but I also love having money, and those two things don’t necessarily work together. So, what did I do right, and what did I do wrong? The Good The best thing that I can say about my career change was that I knew exactly what I wanted to do. I was completely positive at the time that the only thing I wanted to do was write novels; this is a holdover from my childhood, when I would escape into books and into writing. I still feel this way – if I could live in an ideal world, I would write all day long. Another thing I did correctly was I sat down and I actually did what it was that I wanted to do – write. I did not spend a single day wishing that I had more talent, staring at an empty page, or talking to my friends about writing. I treated writing like it was a job, and I did it everyday until I finished a draft of my first novel. Finally, the last thing that I did well (although I should have done it before I even started writing) was that I asked people in the industry how to get my book published. Everyone I asked for help was a cold lead – I simply found their email or went up to them in a crowded room. I learned early that no one helps the shy person. Coming from finance, I had expected publishing to be a meritocracy: I thought that, as I had finished a book, I should now have no problem getting evaluated by agents, publishers and the like. It does not work like that, and I was grateful to have experienced (sometimes best-selling) authors who would answer my questions and help guide me through (and who continue to guide me through) the process. The Bad The most obvious mistake that I made was to quit my job. I had a high-paying job in finance, and I could easily have written on weekends and nights. Moreover, I had an offer out in California, which would have given me even more time to write. I could have excelled at either of these jobs and completed my first novel at the same time, especially as it turns out that I have about four productive hours of fiction in me per day. At the time, I thought that I needed to have all the time I could get to write; had I given more focus to writing while I was still working, I would have seen that I could have done both. The second mistake I made was in my expectations. I have no doubt that I have talent – not then, and not now, hundreds of rejection slips later. However, I should have known from the beginning that getting published is difficult at best for a first-time author. I jumped into writing a novel, anticipating that it would replace my income from finance without doing the proper research. By comparison, it would be as if I thought that standing out on the street with my guitar would land me a gig with the Rolling Stones next week. The third mistake I made was that, once I recognized how difficult my new career was going to be, I did not change course. I decided to keep taking odd consulting jobs (albeit, they started to take up most of my time) and writing, rather than trying a different way to get myself noticed, such as writing this type of blog. Sometimes, a small course correction can lead to big results (and sometimes, it just ends up being movement without reason). I should have been prepared to move more quickly into alternative forms of writing/creating. There are certainly other things that I did incorrectly in my career switch (please email me if you think I’ve missed something major, and I’ll make a correction in my next article), but I think that these are the big three: 1. I left myself without a source of income when I was starting my new business; 2. I did not manage my expectations properly; and 3. I did not react to market conditions quickly. Next time, we’ll go through an example of someone who quit his/her job and started a new career successfully.