When should you make the leap?

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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.

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  • Melissa Kennedy
    Melissa Kennedy
    Thanks so much for the really great conversation here and thanks Jonathan, for sharing your story and your advice here, so that all of us at Beyond can benefit from it.
  • Jonathan Brodsky
    Jonathan Brodsky
    Barbara -- Thank you for your note.  I will be writing articles about how to choose which 'love' you should go after in the future, but most of my articles will focus on what other people have done so that we can learn from their experiences.  However, a quick tip on picking a new career -- many loves are better suited to being hobbies than full-time careers.  Look at your list of 'loves' and see which one other people seem to make a living doing.  Ask them how they started and, if they could do it again, what they would do differently.  Of course, stay tuned for more articles, and I'll try to answer your question in greater depth.
  • Barbara Eaton
    Barbara Eaton
    Jonathan:I am enjoying your career change articles and look forward to the next ones. Will you be addressing further the process of actually choosing a career to change to? I have made, both vountarily and involuntariy, a number of career changes in my lifetime - from food product development technologist to full-time mom to clerical temp to customer service to elementary school lunch lady to middle school library assistant to high school computer lab teaching assistant and finally to my present position as a financial service assistant/office manager. I NEED to get out of this job. It's a one-rep office and we don't have much to sell at present and haven't had much in the 4 years I've been here. How do I choose among a list of "loves" and find somthing that will actually pay?Looking forward to reading more!Barbara
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