‘Plan B’ Can Be Better Than You Think

It’s been a whirlwind week.

On the 7th of September I decided to start looking for a job. This wasn’t the easiest decision to make. After all, I had high hopes for my web business, and liked to think of myself at least as capable as those internet superstars who managed to make a comfortable living from a great idea and a whole lot of passion.

Driven by these hopes, I spent the better portion of this past year creating the social donations site GoldHat, teaching myself everything I needed to learn and building the app feature by feature until it was done. When I began the project I had no clue if I could pull it off, but I did it anyway. Seven months later, I launched the website. I couldn’t have been more proud of that achievement.

A couple months after my “big launch”, however, I realized GoldHat had a little problem: no one was signing up. Every time I looked at my Google Analytics page, I swear I could hear the crickets chirp. This was a difficult reality to come to terms with, and I spent a lot of my time ruminating about whether I should continue with the project or hit the pause button and look for a J-O-B.

I knew that GoldHat still had the potential to succeed, but what it needed was more time and more money. Not having a job gave me a lot of time, but my bank account balance was reaching zero fast. I knew I could borrow some cash from my folks to keep the site afloat but I was loathe to do so. Let’s just say that they’re not exactly independently wealthy, and my living at home certainly didn’t help.

I felt that I had to make a change when I (celebrated?) my one year anniversary living with my parents, and when GoldHat showed no prospects of becoming popular in the near future. I resisted starting the job search because it felt a lot like “giving up,” but the prospect of pouring another year of effort into a project without knowing whether or not I was on the right track was far from appealing.

Should I stay or should I go? That was the question.

I wrestled with this question for the better part of a month. My main worry was that I would get so busy at my job that I would abandon GoldHat, and I certainly didn’t want all that work to go to waste. I had abandoned other projects in the past because I did little else but spend the day working as hard as I could and the evening drinking beer and watching TV. Who was to say that I wouldn’t do the same this time around?

I eventually came the to conclusion that I could keep a day job and keep GoldHat alive. First of all, I had invested a considerable amount of time in GoldHat. I certainly wasn’t going to stand by and let all that effort go waste. Secondly, I feel that I’ve grown as a person, and I have a better understanding of my strengths, weaknesses, and the direction I want to take my life. This elevated level of self-understanding has helped me tap into a store of energy that I hadn’t known was there.

I realized that staying vs. going wasn’t an either/or decision. I could easily do both, and that’s what I resolved to do.

After I made this decision I formulated my master plan: I’d work for a web startup, get a good feel for the business, save a little money, and maybe hire some people to help make GoldHat better. I could also network with startup folks while on the job, and perhaps get a business partner on board who’d be willing to work with me.

The decision was the hard part. The rest was relatively easy. My experience as a headhunter helped make the job hunt quick and painless. I found a list of Seattle tech startups and I sent a whole bunch of introductory emails out to hiring managers and CEOs, regardless of whether they appeared to be hiring or not. The day after I sent my first round of emails I got a response from Dave Schappelle, the CEO of Teachstreet.com. He didn’t mention any open positions but offered to meet me for coffee.

The meeting went well. I got a call the next day from Dave and he offered me a job. I accepted and a draft of my offer came by email later that day. I never expected to get a job with a startup so soon, but I think the folks at TeachStreet were impressed with the work I had done with GoldHat and were willing to take me on because of it.

I’m grateful to my parents for supporting me during this past year. Although they didn’t complain, I know that it hasn’t been easy for them. I’m just happy that they believed in me enough to let me learn and grow (and eat their food!). Although I didn’t make more than about $400 for all my web businesses combined, in terms of personal growth I feel that this has been one of the most productive years of my life.

Some readers may ask, “Is this the end of unreadyandwilling.com?” After all, the tagline is “Adventures in Self-Employment.” My short answer to this is “no.” As I’ve said before, everyone is self-employed, but very few have that self-employed mindset. At times I too lose sight of the fact that I’m self-employed as well.  That’s why I feel that it’s important to continue with this blog.

Note: As I write this I’m already well into my first week at TeachStreet.com. I’m loving it so far and promise to write a blog post about my experience either this week or next.

Some people might be interested about the methods I used to find this job. I’ll be sure to write about that as well. Stay tuned!

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  • Shirokuma

    Great story.

    Reminds me a lot of my situation now. Keep with trying to make a career out of photography or bite the bullet and go back into the insane world of teaching.

    We have decided to return to Kanto so like you maybe I will end up doing both.


  • Glad to hear you’re keeping the sites up. One of GoldHat’s strengths, and I might have mentioned this, is that it doesn’t *need* to have you chasing after it 24/7 or an army of coders burning cash on it to work.

    Also, Unready and Willing is a pretty key sentiment to this new age of chaos we’re living in, and as you said, we’re all self-employed now.

  • Great to have you on board at TeachStreet, Kenji — we honestly weren’t looking to hire anyone, but I rarely pass up the opportunity to bring someone on board who is curious, willing to self-teach/learn/explore, and who has an entrepreneurial fire. I think you’re going to be a star — we have a lot to learn from you, and you’ll learn a lot from the folks on the team — even though you’ve only been working with us a few days, you’re already adding value/ideas/energy.

    And, yes, we’ll ALL self-employed — most people just don’t realize that and/or act accordingly.



  • Kenji

    Best of luck with the new job and keeping up with the photography on the side. I think we have the tendency to belittle side-projects as nothing more than “hobbies” but there have been plenty of instances of people who have become successful with a vocation they’re passionate about while keeping a day job. It seems like common sense, but I’ve had the “all or nothing” mindset for the longest time now.

    You’re a great teacher and a great Photographer. The latter will keep you happy. The former will keep you fed.

    I suppose that because I had no money, I refrained from implementing features that required a serious investment. Now, just after a week of working at teachstreet, I have a feel of what it takes to keep a web startup well oiled and running. Right now Goldhat doesn’t have many users so the costs are minimal. If it had as many as teachstreet did, I think it would be a different story.

    Thanks for stopping by Dave. It really has been quite the culture shock transitioning from the stiff and stodgy culture of Japanese businesses to the more relaxed culture of Seattle startups. Actually, the relaxed environment seems to encourage more productivity. Looking forward to growing and learning more with the team.

  • Julio

    I just recently discover your blog and have enjoyed your very insightful, wise and articulate posts. You have acquired at a very early stage in your professional life the kind of wisdom which takes other professionals decades to acquire. I can see it is serving you well already.

    While through my 20+ year professional career I have had my fair share of steady pay checks and perks attached to being employed by someone else, I also always considered myself as if I was self-employed and conducted myself and my career accordingly. I eventually jumped tracks at a stage of my career that made other people (particularly my wife) think I “had lost it”

    I cannot say it’s been a bed of roses and have not reached the objectives I set for myself by this time, but I have enormously enjoyed it, do not regret it and am still very hopeful that in the long run it was the wisest decision I could have made.

    Hope you continue to write and good look in your new endeavors.

  • I thoroughly enjoyed reading your post because it was honest and from the heart. The difference between you and other wannabe entrepreneurs is that you put your nose to the grind and went for it. Your decision to seek a J.O.B and the fact the Dave saw your brilliance and hired you practically on the spot, speaks volumes about both your work ethic and yes… your brilliance.
    I dont remember how I came across TeachStreet but I loved the concept they were offering and the name was a big thumps up. I’m glad I signed on because I got to now meet you and hear your story.
    Go for it … you’re on the right track and best wishes to you and the team at TeachStreet.

  • Hey Kenji,

    Genki de gambatteru mitai dane. I hope your experience at Teachstreet.com is another huge step toward self fulfillment. Sometimes things that life throws at us can be seemingly off, but as long as you keep taking a step toward your goals, it becomes inevitable, no?



  • Kenji

    Thanks for coming by, and welcome! I’d hesitate to say that I have acquired any real kind of Wisdom in my six years of work experience, but I have an idea of what to aspire towards, and that does help. I’m glad to hear from another entrepreneur who found the leap to be a rewarding experience, despite the difficulties along the way. If you’d ever like to share them in a guest post please do.

    Thanks for the encouragement and best wishes. I’ll be sure to let you know how it goes!

    Hisashiburi! All I can think of these days is finding a rhythm at my new job, but I have learned that it is important not to lose sight of my goals. I’ve resolved to make sure that I never do (at least most of the time).

  • I have followed you for long awhile. I like your writing style. You are witty and have common sense and say it with a grain of salt and a pinch of humor. I will keep checking your blog to see how life is for you. I am starting a new page its not up but you might like to look at it some time.
    LifeArtStory.com this is in wordpress which I do not know and hosted on godaddy for the next 10 years but the first year I have been stuck in lost land trying to decide what to put on it and publish
    my other blog is on blogspot http://seaaggie.blogspot.com/ this is my trials and complaints about going back to school in my 40’s with a lot of very young persons

    I have really enjoyed your blog Thanks
    Best of success with your future endeavours.

  • Ren


    Whenever I read your blog posts, I feel hopeful.
    I’m a Japanese Studies Major and taking the same in grad school, while taking some classes in Creative Writing to hone my writing skills.

    I quit my job 2 months ago because it was too much that I could not keep up with my studies. I, too, feel the same of not wanting to drain my funds from my last work. It’s really difficult to find a work with my degree because the trend in my country is BPOs and call centres. I don’t want to go back to that industry anymore . Hope i can find a job that i can compromise work and school.


    Wish you all the best in your plan B!!!
    I hope it goes tbe same to me.

  • Kenji

    Hi Renさん,

    始めまして! I’m so glad my story can inspire hope for just one reader. It’s messages like these that make me want to write and share more. Arigatou!