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Navigation: Home » Blog » You can’t connect the dots looking forward. You can only connect them looking backward.

You can’t connect the dots looking forward. You can only connect them looking backward.

By Andrew C. • Updated: November 29, 2019 • 2 min read • 5 Comments

steve jobs stanford

While on the subject of Apple, I thought it befitting to look back at the commencement speech Steve Jobs delivered at Stanford in 2005.

[embedyt]https://www.youtube.com/watch?v=UF8uR6Z6KLc[/embedyt]

I’m always struck by the story he tells about stumbling into that calligraphy class at Reed College, and how a decade later when he was integrating typefaces into the Mac, he reflected on how it is impossible to “connect the dots” looking forward; but they are very clear looking backward:

“You can’t connect the dots looking forward. You can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. Because believing that the dots will connect down the road, will give you the confidence to follow your heart, even when it leads you off the well-worn path. And that will make all the difference.”

I think it’s important for young professionals to internalize this message deeply as they contemplate career moves that may seem risky looking forward, or may seem orthogonal to what they’ve been doing previously. It takes a lot of guts to pivot into something entirely new, to seemingly press the “reset” button on your career (and perhaps to press it a few more times down the road). I’ve done it at least half a dozen times. I know many others who have done it, too.

But in ways large and small, my past experiences have sometimes converged at various points along my career path. And I deeply believe that the diversity of these experiences — and the knowledge acquired with it — while perhaps “slowing things down” in the short-term, will come together in the long-term in serendipitous, delightful ways to open and accelerate new career and life opportunities that wouldn’t have been available otherwise.

As you contemplate “scary” career transitions, definitely evaluate the risks carefully and make your decisions thoughtfully, but remember that you can’t connect the dots looking forward. You can only connect them looking backward.

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Tagged With: Apple, calligraphy, commencement, dots, font, mac, reed college, reset, stanford, steve jobs, typeface, typography

About HYW

I started Hack Your Wealth in 2015 because I was frustrated by the quality of “financial independence, retire early” (FIRE) content on the web. I found much of it to be generic personal debt journeys, but that didn’t help me because I already routinely saved over half my income. What I wanted instead was deep, analytical, step-by-step insights – and hardcore spreadsheet tools to match! – on how to rapidly grow wealth and manage it strategically and tax-efficiently to get to financial independence…all while raising a family. So as I became increasingly expert in wealth management, tax-planning, and estate planning, I started documenting the biggest strategies I was thinking long and hard about. That content became HYW.

What are my bona fides? I cut my teeth at McKinsey and HGGC private equity (Bain Capital spinout), picking up a CFA along the way, before going into product at LinkedIn, Redfin, Pinterest, and Google. BA from UT-Austin, JD from Harvard Law School. Licensed to practice law in NY, CA, and HI.

These days, I get a kick out of interviewing guests on the HYW podcast about wealth management, tax-planning strategies, and life hacks; getting the occasional dopamine rush after scoring a juicy travel hack award; and showing my hilarious and silly(!) daughter all the tricks she needs to know to have an epic childhood. Read more about my story.

5 Comments

  1. Christopher Gabe says

    May 1, 2018 at 5:11 am

    thanks for your comments

    ▾ to Christopher Gabe'>Reply ▾
  2. Tommy @ LeisureFreak says

    March 14, 2016 at 4:44 pm

    Very true. I found that as long as I move forward that things tend to go toward our destiny. If we continually learn new things, do our best, and work towards our goals we will reach them. However the final destination or goal may be different than the one we initially planned because the future and newly discovered goals are unknown until they are revealed. Looking back I can connect my dots but it sure seemed random and indirect while in the moment.

    ▾ to Tommy @ LeisureFreak'>Reply ▾
    • Andrew C. says

      March 14, 2016 at 7:49 pm

      Thanks for sharing this!

      ▾ to Andrew C.'>Reply ▾
  3. suhendri saputra says

    February 4, 2016 at 1:00 pm

    It is so awesome.

    ▾ to suhendri saputra'>Reply ▾
    • Andrew C. says

      February 4, 2016 at 1:14 pm

      Thanks for your comment!

      ▾ to Andrew C.'>Reply ▾

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