10 Things I Wish I Knew Before Entering the Workforce

by Scott - 7 Comments

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I’ve learned a lot from New York entrepreneur Vin Vacanti through his blog “How to Make it As A First Time Entrepreneur“. Recently he wrote a post on advice he would have given himself 5 years ago. It’s a great read that I suggest you check out.

Vin’s post inspired me to do some reflecting on my own journey. Here’s 10 things I wish I knew before entering the workforce 2 years ago:

Before Graduating

Nothing is more valuable than a mentor. When anyone young approaches me for career advice, I tell them to find the person whose best at what they want to get good at and go work for them – assuming you’re simpatico of course. I’m all about baptism by fire – but without an experienced mentor to calibrate your experiences, you’ll learn at a much slower rate and the process will be less enjoyable.

Busyness does not equal productivity. For the longest time I equated relentless busyness to solid progress even when I was opting for the path of least resistance. I’d clean my room before I could sit down to write a paper. I’d run errands instead of doing a problem set.

I’ve learned that the most successful people focus on figuring out how they can add the most value to whatever scenario they’re in and then execute, according to a well-thought out hierarchy of tasks. Often that means doing what’s hardest and slowest first.

Fortune favors the bold.  I knew this before I graduated, but didn’t start really living by it till later on. I’ll never forget one family vacation where I was out to dinner and we had this beautiful hostess that my family was cajoling me to go talk to.

“I’ll talk to her on the way out,” I said.

They left a minute before me to give me the open window. When I walked out…well, I just walked out. They were all waiting outside the car.


“I didn’t talk to her.”


“I didn’t have the balls”

Well, the ones with the balls win.

I’ve never forgotten those words. Be it vacation romances or our careers, you never hit a shot you don’t take. I have a feeling that there are far more people who regret not taking more shots early on than people who wish they hadn’t taken so many…I wish I had started taking threes earlier.

Wake up early. Its amazing how shit doesn’t get done after 7 pm. We grab drinks instead of going to the gym. We watch Newsroom instead of slogging inch by inch towards our long term goals.

The past year has been the most productive year of my life and I mainly attribute it to one thing: waking up early. I spend the first few hours of my day working towards the things that are most important to me that I often find excuses to put off – no one’s giving you an out to grab a cold one at 5:45 am. I wish I had implemented this practice earlier in my life. It’s become my favorite part of the day. Besides, as James Altucher says, nothing good usually happens after 10pm : )

Always think long term. I was thinking about this the other day – when’s the last time I made a decision that was best for my long term interest and truly regretted it? I couldn’t think of one. However, I have no problem recalling many decisions early on in my professional journey (and life) where opting for my short-term preferences came back to bite me. It can be really hard to delay shot-term gratification, but I’m pretty sure it’s harder to change a previous decision that begets disappointment.

Carry a notebook in your back pocket, everywhere. I know this sounds ridiculous, but nothing has provided a greater intellectual jolt in my life than carrying a notebook with me wherever I go. I started doing this just over a year ago. There’s something so amazing about capturing every fleeting moment of brilliance we have – it frees me from walking around thinking about having to remember my thoughts because I can just write them down. I’ll spare you the details in this post because I’ve already written about how carrying a moleskin has changed my life before.

Lead with value. There was a point in my life that I was plagued with a “what’s in it for me mindset.” Nothing could be a bigger barrier to success for a young person than this attitude. Quite bluntly, I’ve learned you’ll go much further providing value to as many people as you can with little expectation for anything in return. Thanks Keith.

Always follow up. I missed out on a lot of opportunities early on because I didn’t follow up. I’d timidly throw my hat in the ring and if things didn’t pan out after the first try, I’d take solace in the fact that “I tried” and walk away. In hindsight this was so dumb.

Whatever the context, often time the reason that people don’t get back to you is not because they weren’t interested, but rather because something completely trivial happened that was out of your control. Don’t let something like someone else forgetting be the barrier to you seizing an incredible opportunity.

Life without balance has costs. I charged pretty hard professionally when I first got out of college. It’s done some good for me, but it’s also cost me in many ways. I’ve grown apart from friends and probably missed opportunities to meet amazing people for things that ultimately didn’t mean all that much. Damn AppSumo videos. The good news is, I’ve knipped this in the butt and have been making my way back to where I’m happiest – balanced.

There’s definitely a few other things I’m missing here, but for now I think this is a good start. I wonder what I’ll say I wish I knew when I was 24 in a few years. If there’s anything you wish you knew before entering the workforce that you’d feel like others would value, please feel free to share in the comments.


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7 comments, add to the conversation.

  1. Andrew Bryk

    Great post. I really enjoyed it. Do you find it more productive to use a notebook as opposed to an iphone to jot down thoughts? I use my iphone as a notepad and am wondering if you think there are benefits of writing it down by hand?


    1. ScottBritton

      Thanks man. I definitely find it a million times more productive/enriching to use pen and paper. My phone is a vacuum of digital distraction. I’ll go to take a note and see someone tweeted at me, check that and forget the note I wanted to remember. Pen and paper removes instances like this. Try it


    1. ScottBritton

      Thanks and exactly. I do like to spend my evenings with friends/professional contacts and beer is involved from time to time : ) I can really enjoy these moments instead of feeling guilty because I know I’m going to go to the gym, write, or finish a project early in the A.M.


  2. blake41

    An interesting thing I’ve learned is that going to Dartmouth was as much of a prison as it was a door opener. Even though post college I’ve hardly taken the traditional path, I subconsciously avoided pursuing certain things. Dartmouth students should make a certain income, have certain jobs, shouldn’t fail at anything, have a certain level of success etc. etc. I had a whole bunch of bullshit made up in my head that kept me from doing what I really wanted to be doing (which was programming). If I started over I’d have to be a novice. I’d have to ask stupid questions. I’d make no money. I might never get a job. There were so many fears I had that I didn’t even consciously realize I had. Realizing my fears, and the mental prison I had put myself in gave me a new lease on life. Starting over was incredibly powerful. Being able to admit I didn’t know all the answers. Humbling myself and asking many people for help was life altering.


    1. ScottBritton

      Awesome stuff man. I totally agree that expectations our environments put on ourselves (at times unknowingly) can prevent us from pursuing what we’re meant too. It’s hard not to pit our progress against these benchmarks, but I find questioning the benchmark can help. I.E. Should I be measuring against “success” or happiness – “prestige” or freedom. etc


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