First few lessons learned as an entrepreneur

It is  hard to believe that it has already been three weeks since I left my day job. Although I have yet to start on what I would consider to be my real startup, these past few weeks have been really busy. I’ve been working on an existing project, my email-to-Twitter service, and trying to figure out how to maximize revenue without continuing to spend a disproportionate amount of effort developing and maintaining the service (this is both fun and frustrating).  Now that I am on “Christmas vacation” (mandated by the big boss), I thought I would take a moment to reflect on a few things I’ve learned during my first few weeks as a full-time entrepreneur:

It’s tempting to move too fast

My last day as a full-time employee was on a Monday and I immediately hit the ground running on Tuesday. Since then I’ve been trying to move at a break-neck speed. There is an enormous sense of urgency and I’m now able to move fast without other commitments or distractions in the way.  Sounds great, right?

The problem is that it is really easy to get sucked into task after task and feeling like you can’t waste time by doing anything else. Should I  take 30 minutes to catch up on RSS feeds and my Twitter stream? No way. Take a shower and eat lunch? Maybe later. Can I just stop and think? Ah, when I have more time.

Obviously, this is not the most effective mode of operation because there are valuable benefits (both direct and indirect) to those other activities. I have to keep reminding myself: Move forward as fast as you can but don’t lose your balance.

Time truly is money

Perhaps the biggest shift in perspective when moving from a salaried day job to self-employment is the realization that you make money based on how you spend your time. This may sound painfully obvious — and it is — but it’s not something that I fully appreciated  as a salaried employee. After all, I had no way of measuring the impact of my contributions to the bottom line, and even if I did, it would not have affected my compensation in a meaningful way.

Now, everything  I do involves an ROI calculation. This is both good and bad (see point about “moving too fast” above), but overall I think it makes sense to operate in this way. There’s no denying it: my income is a measure of how well I convert time into money.

Multi-tasking is necessary but inefficient

Our intuition tells us that being able to do multiple things at once will make us more efficient overall. The truth, though, is that most of us are *not* able to work through multiple things at the same time: there is just too much cost associated with task-switching. We are often more effective when we focus on one thing at a time and move through our tasks sequentially.

This is not necessarily a new realization for me but it is certainly a much bigger problem. As an employee of a large organization, I always had a lot of different responsibilities but they fell within the general scope of a software engineer. As a solo entrepreneur, on the other hand, I am responsible for everything: understanding the market and competition, keeping up with news and trends, prioritizing features, designing the look and feel, writing the documentation, composing and sending marketing emails, reaching out to potential business partners, acquiring press coverage, monitoring analytics, supporting existing customers, and — oh yes — developing the software itself.

Figuring out which activities to prioritize and when to work on each them is tough.  It is very tempting to continually switch between tasks to ensure that I am making progress on everything that is important, but ultimately this tends to slow me down. For now I am approaching this problem like a software engineer: Schedule tasks as meaningful but atomic activities (i.e. must be completed from start to finish) and execute them in sequence.

In many ways, the issues I’ve described above are not unique to self-employment; everyone has to deal with time management and task prioritization. How do you deal with your insanely busy day? I’d love to hear your thoughts.

7 thoughts on “First few lessons learned as an entrepreneur”

  1. Anil, you provided great insight here. I find your tips especially useful for start-ups in healthcare. Healthcare is a very complex field and prioritization is key with execution in sequence as a must!

  2. Wow.
    I feel like you and I have to talk.
    The Universe is conspiring to connect us.
    As you know, I’m a user & fan of your twitter-to-email service.
    After being outspoken about my feedback about it recently, on twitter, you asked to discuss my impressions more.
    Since then, it’s been brewing in the back of my mind… What the best advice. / recommendations I could give you… would be.
    Then, today, the thought hit me! Like a truck!
    I also have a spouse partner who is my “confidant and advisor in all things”… I was telling him (Ed) about this new sustainable business model for internet startups, which I had heard about through my buddy, Leo Laporte.
    I had no sooner explained it, and the simple beauty of it, to Ed… when it hit me. I said, “You know what business this model would be perfect for!?” Ed said, “TweetyMail.” ( He knows how my mind works so well! 🙂
    Obviously, we have to talk. Call me on the phone when you get a minute. 646-580-0022 or [email protected] ( Don’t worry, these are no secret.)
    Then…. while trying to find your email address, I discovered your blog just now.
    Of course, I read it.
    I had no idea this was such a small, new startup. Congratulations.
    I’m a huge believer in following your dreams and passions. They know where you’re meant to go.
    Then, I read this item.
    I can so relate.
    As Ed tells me, “You think like a computer.”
    Of course, he’s right. We geeks can’t help it. We do.
    But…. in trying to tackle this exact dilemma: time management for maximizing results for the one-man entrepreneur ….
    I’ve finally learned to embrace those “programming skills” mindsets, and I approach it that way.
    Warning: It’s very tempting and easy to make it overly complex.
    It’s also easy to over-correct for that and over-simplify.
    For me, it’s somewhere in between.

    I ride like this:

    My days are driven by my (alternate gmail calendar) called, “Daily Routine”.
    It’s the same every day. Rigid.
    6am up, pray & meditate
    6:30 – 7:30 workout
    7:30 – 8:00 shower, get ready
    8:00am – 10:00pm work on “income producing business” (aka “the day job”) until a specific goal is reached, then work on “passion venture”
    10:00 ready for bed, sleep


    Sleep is one of the most important tasks on your routine. As is exercise. Ad is nutrition.

    I give myself a specific “day job” ( income-related ) goal for each day. So I FOCUS solely on that until it’s reached ( untilled I’ve either scheduled 2 billable hours, or completed 1 — that’s my specific daily goal ), then I switch modes.
    Then, I turn off that business and I focus solely on the business I’m passionate about — my new startup.

    Overlapping that Daily Routine are certain other things, of course:
    Prescheduled billable hours (trumps everything else)
    Special ocassions (like Broadway show tickets – semi rare)
    Meeting and conference calls ( try to minimize these, only when essential, concise as possible, and include as few people as possible )

    Then, I maintain an outline in Google Docs…
    For each time block on my Daily Routine, I have s section on that outline which acts as a checklist, in sequential order, of what I’m to do every day at that time. ( It may seem overly anal, but I find it faster and easier to follow a checklist I’ve created. I don’t have to think. I never forget a task. And I’m constantly tweaking and improving and refining my own process – the details of my own routine.

    Then, in my main “work time” (8am-10pm), the last task on that short little Daily Routine checklist is… one of what I call Time Cycles.
    It says, “Do ‘startup’ cycle for one hour”
    Or, at another time it might say, “Do household cycle for one hour.”

    The next outline section in that same Google Docs document I call “Cycles”.
    There’s a business cycle, startup cycle, a household cycle, and even a giving cycle.
    The idea is: They are like a looping subroutine. They are a list of things I’ll want to do, or touch, or check on, on a regular recurring basis.
    One is all the regular tasks for my income-producing business. One is all the recurring tasks for growing my new startup. One is even a list of all the things Ed’s always reminding me to do around the house, on a regular basis.
    I cycle through a given list, returning to the top of that cycle list when reaching the end, for the amount of time specified in my Daily Routine. It might be one hour, or 2 hours, or “until end of time period”.

    So the Daily Routine checklist is things you must do, without fail, every single day – preferably at the same time, or within the same block of time.

    The Cycles are subroutines called from the Daily Routine Checklist, and are things you should do (or touch, or check on) on a recurring periodic basis – but not necessarily getting to each thing every day.

    Then, finally, I have the third section of my outline document, which is my Master Projects Outline — which is exactly what it sounds like — every non-recurribg task organized as largest project, then sub-projects, etc, etc, down to tasks, and sub-tasks. I leave the “next action” in each highlighted in yellow.
    “Work on Next Actions for one hour”, for example, can be called from one of your Cycles, and/or your Daily Routine Checklist.

    This all might sound overly complex. For some people (like Ed, for example) it’s unnecessary. He multitasks intuitively. However, for me, I find that by structuring my attention more, I’m multitasking less ( far fewer interruptions ), focusing more, and in the end… getting a LOT more accomplished.

    Obviously, there’s a lot more to being productive, like:

    Continuous tweaking of these outlines – continuous improvement of your daily routine checklists, time cycles, and master projects outline. They are living and breathing documents which needed tweaked and improved and refined constantly, as your life and business and goals evolve.
    ( I keep them all in one single Google Docs document, with a shopping list too, for easy viewing and editing at all times, even from my Android phone. )
    Learning to say No. Gracefully Declining invitations and requests for “help” from friends.
    Getting Smart Assistant(s) — unpaid interns, paid staff, or business partner(s), working with smart people, and learning how to manage people and get them to strive for excellence, is an art…. and a very necessary talent.
    Great people will allow you to offload 95% of what you do now…. allowing you to laser focus on the big picture, and zoom in on the details as needed… without drowning in the quicksand of the details.

    All the best,

    Bruce Wagner


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