What’s Your Big Decision? (My 27th Birthday Giveaway)


So I turned 27 about a week ago.

Last year, for my 26th birthday, I had a giveaway where I asked you, readers, to share your biggest lesson you wish you learned when you turned 26 — or who you hope to be by then if you were younger than me.

That was a lot of fun, so let’s do it again!

The giveaway: Decisive by Chip and Dan Heath – a phenomenal book about making better decisions, not through a soulless spreadsheet, but with sound and proven psychological principles. One lucky commenter gets a free copy (closes June 6th)

The request: Leave a comment about an important decision you made in life and what you learned from it.

Here is mine:

Choosing to work at the Stanford Daily

When I was getting ready to graduate Stanford, I interviewed for and was offered the job as the Chief Operating Officer of the Stanford Daily. It would be a full-time, one year paid position for a recent grad to run business operations for our student newspaper. I was also in final round interviews with Teach For America and the Coro Fellowship in Public Service.

The role at the Daily was less prestigious and I had no particular experience working at the newspaper. It would be local. TFA and Coro could potentially take me far away from the Bay Area and would take me down the road of public service.

I spoke with a mentor of mine, Dan Gill of Huddler, and he told me something I’ll never forget: “It’s rare to get P&L (profit and loss) experience so early in your career, and that’s a really valuable experience. Since newspapers are struggling, if you fail, no one will blame you. And if you succeed, you’ll look like a hero. It’s a no lose proposition.”

Now I’m not saying you should always think about decisions in this way, but that advice made a lot of sense to me and I took the Daily job. It was tough and we did struggle, but I think I did make some lasting contributions to the organization. And I’m really glad I took the job – it put me down the path of business, lead me to working at isocket, and well, the rest is still being written. =)

Alright, well, that’s my story. What’s yours?

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  1. My big decision was made when I was 17. I was an exchange student living with a lovely french family in Hossegor France. I had been there 2 weeks and was seriously homesick. I called home to ask if I could come home early. My mom asked me one question. She wanted to know if I came home now, would I want to return and complete my stay. I told her,of course! just then, I realized how silly that was and decided to be an adult and finish what I had worked so hard to achieve. I had the best time and appreciated my french family and my moms advice more than I could fathom. Im now 26 years removed from this experience and can recall my feelings during that conversation like it was yesterday.

    • @Jmiller8816 That’s an awesome story and great on your mom for asking that question!

  2. My big decision came earlier this year. I work in politics and I was looking for a new job after the 2012 election and I had multiple offers at the same time and had to decided between the two. The first job paid better, would utilize more of the talents/skills that I already had, and was closer to my family. The second job was an opportunity to develop brand new talents/skills, expand my professional network, and potentially fast track my climb up the leadership later. The former seemed to me like the easy/comfortable path that would give me more short term gain, but I decided do the uncomfortable and chose the later. The end result to this decision is still being written, but I am happy with my decision. I think the main thing that having taking away from this decision is to not just do what is comfortable and to challenge yourself to do more, I chose what would benefit me more in the long run vs short term.

    • @charles87 That sounds like a tough decision and thanks for sharing. Discomfort often leads to growth so I wish you the best with your new opportunity!

  3. Choosing to change my major…again. When I applied to my university I applied as an art major. After my first year I switched to pre business. After all of that I still didn’t like where I was going but I felt stupid for switching so much all ready that I didn’t want to tell anyone and stayed in pre business for the next semester. Finally I decided to talk to my sister about it and she told me that I’d better figure out what I want because after you graduate you don’t want it to be for nothing. So I finally decided to declare my major as Biology and have never been happier with my classes, even chemistry.

    • @BSaltlakelovely Great story BSaltlakelovely! Deciding to change again is tough too because you’re forced to admit you were wrong about the initial change. But it sounds like you’ve found a better fit so good for you! I was a bio major too – I don’t really use it as much in my work today, but I’m glad I studied it.

  4. Last year in october I was really fed up that, despite my seemingly hard effort, I failed to get with any girl at all. I’ve been unwillingly single since over two years. Back then I lost my last (and first) girlfriend and I thought, even with her I had just been very lucky.
    I’ve never been the social type of guy and I figured the only way I could ever change this was making a top-level commitment to this area and exerting all my efforts. Thus I ended up being on the road more often then not. I spent on average two of three days getting rejected by hundreds of girls (I found your blog by typing into google guess what – “rejection therapy”) and getting my ego crumbled many, many times…. And after all, success happened and more than I expected. In the end I ended up being in a relationship again – with a unbearably sweet brazilian girl :)
    But what made it really worth it, is that I feel I grew internally. I now feel mature than before, and on some note more serious.
    The only bad thing was, due to this endeavor I neglected university for several month and a have now a shitload of work to catch up on. So actually I should not spend my time writing blog comments.. ;) but I still hope this was worthwhile to share

  5. Tarique emailed me this and I wanted to drop it in here:
    Two years before while I was struggling without any saving, made up my mind to start my own business.I decided to abandon my job and starting the venture. Now after two years I am much better with my growing business. I am proud of my decision.

  6. Anant shared this via email as well, so thought I’d put it here.
    Belated happy birthday Jason! I was entering business school when I turned 26 and shall be 28 this september. Anyway the biggest lesson I have learned is no amount of planning will guarantee success and its very important to take chances.
    For eg, some of the roles I interviewed for which did not come my way, in hindsight if I offered to work for these companies for free for 2/3 months would probably have led to a better outcome and they most probably would have allowed me to work for them. But this option never occured to me after having graduated and an EMI to pay towards my student loan.
    The practice of volunteering to work for free is not prevalent in India but by now I would have been better off. With the financial pressure, it might be too late now. But as my personal motto I’ll Never Give In! Cheers – Anant

  7. This is a bit late but my cousin just pointed me to your blog. About three weeks ago, I decided to resign from my company. 
    I was working at Homejoy and had helped grow the company from just one market served and a few hundred customers to 18 markets and thousands of customers. I’d seen the company grow from a team of 4 to a team of well of 50. 
    During my morning meditation that Monday, I got the feeling that I was spending my time in the wrong pursuit. I was focusing on too many things external to me that I didn’t have enough time to focus on myself and my growth. I went in, talked to a few friends and family members, and then told my boss at the end of the day that I’d like to leave Homejoy soon. By the end of the week, I was officially resigned.
    I left to focus on my personal growth and serve others around me however I can. I’ve started to pay better attention to the situation and reflect more. I haven’t made a single dollar yet but I am happier than I’ve ever been. I’ve written two blog entries and I’ve gotten over 1,000 views. So many people have given me their support and I’ve been able to help many people in big ways. 
    I learned that if I pay attention to the moment, I’ll find a way to be happy that helps others be happy too.

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