Startup Conversations With Myself: What Should I Work On?

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Startup Conversations With Myself: What Should I Work On?


Entrepreneurs (particularly bootstrapped ones) have a tough life.  In the early days, things can get lonely.  So many decisions, so many challenges, so much to do — and very little by way of clear answers.

This is a somewhat light-hearted episode in perhaps a series of articles that I’m calling “Conversations With Myself”.  I’d like to think that I’m not alone in my strangeness in that I actually have these kinds of debates going on inside my head (often after 3:00 a.m.).  My guess is that some of you have variations of these kinds of conversations yourself.  If not, then I guess I’m just weird.long list

Conversations With Myself:  What Should I Work On?

Me:  Self, I’ve been thinking a bit about things.

My Self:  Are you you sure you’re not just procrastinating?  Don’t you have bugs to fix in the product or some other real work to do?  Thinking is for smart people.  Get back to work.

Me:  That’s just it, there’s just way too much work, and the list of things to get done seems to get bigger every day — even though I’m staying up later and working harder.

My Self:  So, what’s your point?  It’s a startup, that’s the way it’s supposed to be.  If you don’t have 10X as many ideas as you have time to do them, you don’t have enough ideas.  Quit being a whiny-assed pansy.  Nobody said it would be easy.

Me:  Yes, yes, I get that.  I know startups are hard with the 80–hour weeks and all that.  What I’m saying is that there are several items in the backlog that must get done.  And, as the product gets bigger and more users come on board, more and more time is taken up keeping the system running, responding to user issues and a bunch of other stuff.  When will the new stuff ever get done?

My Self:  Ok, so define “MUST get done”.  What happens if you don’t do some of those things?  The planet stops spinning?  You lose some users?  Your ego gets bruised?  You watch one more episode of “The Office”?

Me:  Ok, fair point.  I guess not all of those things are technically “must-dos”.

My Self:  Well, it actually goes beyond that.  Not only are most of the things on your list not “must-dos”, a lot of them are probably “shouldn’t dos” .

Me:  So, how do I go about figuring out what I should get done? 

My Self:  That’s a great question.  Unfortunately, we share the same brain, so I don’t have a great answer.  But, here are some things to consider.

Simple Tips For Deciding What To Work On

1.  Are you tracking all of the bugs and enhancement ideas (however crazy) somewhere?  If not, that’s step 1.  You need a central list.  Not this list and that list, but THE list  The One True List.

2.  Decide on a simple and semi-objective approach to classifying each item on the list.  Scales of 1–10 work reasonably well.  Some high level dimensions could be: 

a) This will help make customers happy (0–10)

b) This will help me sell more customers (0–10)

c) This will reduce costs of keeping customers happy (0–10)

d) This will give me and my team joy and happiness (0–10)

e) How much effort will this take (0=Several lifetimes.  10=Hardly any work at all.)

Of course you don’t need to have those specific attributes, but you get the idea.  Here’s why this is more useful than simply trying to assign a “priority” to an item.  First off, many items in the backlog often have more or less the same priority.  It’s hard to decide between them.  Second, priorities change as things happen.  You might wake up one month and need to focus as much as possible on getting new customers.  Another month the priority might be to take your existing customers and make them happier (so they stay customers).  By assigning the above attributes to each backlog item, you can “sub-sort”.  The key is to remain flexible, while remaining mindful of the costs of task-switching  when you change your mind.  Maintain a steady velocity and keep cranking away at the items that are important.

Item (d) above is interesting.  Why should you care whether a given task on the backlog will create internal joy and happiness.  Shouldn’t we all be maniacally focused on customers and make money?  Sure.  But, startups are hard work and trying to continuously perfectly optimize is sub-optimal.  Every now and then, you need to do some things that might not make sense, but might delight users or delight yourself or just plain allow you to sleep better at night.  It’s worth the investment simply to keep spirits and energy up.

3.  Try to build a rhythm for getting stuff done.  It’s a great feeling when you can “feel” the forward progress (however small).  If you get stuck on some project, put it aside and crank some of the other ones out.  Don’t go too far down the rabbit hole for any particular project or task.

4.  You should try to balance the kinds of tasks and projects that you select.  Don’t work just on new features that will help sell the product.  Or just work on things that make the UI/UX better.  Or just work on system optimizations that make your costs lower.  It’s important to pick a variety of tasks (with emphasis on whatever seems to be the bottleneck in the business right now).

So, what are your clever little tips and tricks to make sure you’re working on the right things?  Do you struggle with trying to decide what to do?

Posted by Dharmesh Shah on Mon, Mar 23, 2009


I was just discussing this with my partner. I feel overwhelmed to the point of doing and achieving nothing! 
I need rythm...... 

posted on Monday, March 23, 2009 at 11:00 AM by Martin

Mine goes something like this 
ME: question? 
MY SELF 1: answer?? 
My Self 2: answer ??? 
My self 3: answer ???? 
Just more questions. 
I think i need to get that rythm thing going... 
Nice article. 
ME: now back to work!!!

posted on Monday, March 23, 2009 at 11:21 AM by bruce

Above all those questions the uber-question: this will add values to my customers in a manner they'll easily understand and that I'll be able to monetize in a meaningful way.  
If your product or service doesn't add value (think the Cell processor of the PS3), or if customers don't understand why it adds value (think Blu-Ray), or it adds less value than it costs you (Blu-Ray again), skip it and move on.

posted on Monday, March 23, 2009 at 11:46 AM by Michael

Your article just reminded me of an application idea I had for my product that would enable a management team to prioritize this very list... Thanks

posted on Monday, March 23, 2009 at 11:54 AM by Chris Allen

My main thing is to keep focused and control what you can and do not worry about what you cannot control.Have confidience in yourself, your abilities and your vision. Execute, exectue and exectue is the only answer when you bootstrap a start up, there will be better days ahead

posted on Monday, March 23, 2009 at 11:56 AM by Sanjay Maharaj

Nice article Dharmesh. I totally empathize with the loneliness and ever lengthening to-do lists!  
Independent of discriminating amongst competing priorities, there are two techniques I've found useful in maintaining forward progress in general: 
- From Dave Allens great Getting Things Done, the notion of the 'next action'. Often the tasks on the list are so huge that it never seems like the right time to tackle them. But by just focusing on what the next necessary action is and doing that I find big tasks move themselves to completion. 
- And from Covey's Seven Habits, Sharpen the Saw. IE context switch to improve your ability to be productive or successful - get some exercise, take in an Open Coffee session or whatever. I've done some of my best work while walking the dog! 

posted on Monday, March 23, 2009 at 12:29 PM by Tony Confrey

another way to prorotize the backlog(or work) is use MOSCOW 
Must Have (should be done) 
Should Have (should be done) 
Could Have (If time) 
Would Have (If more time)

posted on Monday, March 23, 2009 at 12:41 PM by Jasvinder Singh

I have recently been suffering from the whole "too much to do" analysis paralysis described above. The thing I've found that works the most for me is just to start on things that are very small, and can be completed within 5 minutes or less. Update the wording in an email template, make a minor CSS change, whatever. Anything that gets me in the code. Once I start completing small things, it's much easier to get myself working on the larger things that really need fixing. It's like a "snowball" effect. I always align it with the famous "debt snowball" method for getting out of debt. Pay off the small stuff first, and it builds real excitement and momentum to tackle the larger stuff.

posted on Monday, March 23, 2009 at 12:49 PM by Vance Lucas

Has anyone had experience getting out of the gates, we have spent almost a year starting up, and getting our service completed, we haven't made a dime and in fact have actually spent much more money trying to get up and running than I think we will make back in the next 5 years. We have a laundry list of to-dos, and haven't had a sniff at success. We get people telling us all the time we have a great idea but we can't get off the ground. That's what keeps me up at night. Self: have you spent more time and money on something that will never fly?

posted on Monday, March 23, 2009 at 1:46 PM by Michael Klear

Why haven't you launched yet? It seems like an idea where it's easy to validate the market by starting with a very minimalist feature set. Build a site with a few forms that dump submissions into a database( you could even use Salesforce or DabbleDB if you really want to save time). You don't bother with automated processing/scheduling/payment until you start to get uptake. Start in one location and buy ads to recruit students. When you have a good pool of students, buy some ads to sell the service. See if the model is working and then iterate from there.

posted on Monday, March 23, 2009 at 11:51 PM by Patrick Fitzsimmons

I use a 5 point priority list and pick one project to work on for 7 days. Just one thing that I want to get finished for the next 7 days. Nothing else.  
Does it always work? No, but it gives me focus to work only on what's important, not urgent which creates frustration for me.

posted on Tuesday, March 24, 2009 at 12:00 AM by Georjina

Hey Michael Klear - you have a great idea. Keep going - you may wake up in the middle of the night with new found clarity. Maybe you just need a rest - but you're probably very close to making it happen. 
I've given you 2min of my time - but it's worth it. Good luck.

posted on Tuesday, March 24, 2009 at 4:13 AM by Ian

Good post and thoughts about prioritizing. I myself (as I write this at 4:15am) have similar conversations with myself. 
I think what you outlined is great to get an initial idea of the rank of a list. But I typically like to do one more thing before I commit resources or my time to any one item. 
I'll look at the top few items (which usually seem all of the same importance) and find the minimum viable way where I can test that feature. Typically that is something like throwing up a link, landing page, or a shell of a feature and measuring conversions and how users interact with it. These are all things that can be done in one day or less and provide valuable data that help lead you in the right direction before committing more time to that item.

posted on Tuesday, March 24, 2009 at 6:38 AM by Brian Balfour

Patrick -  
we launched with our original idea about 2 years ago had very little traction because the logistics of billing and then paying our "student nerds" was too expensive to keep doing and we found that advertising on the college campus's was very time consuming and marketing was much more than we could bring in. So we changed, during this process our programmer who was a 16% partner bailed out, so we were left with no programmer and a changed focus. Now we just had our second programmer bail and we were paying him $1500 for what would be about 2-3 weeks work. Now we are back to the drawing board for programmers we would like to take on a programmer for equity full time so that in the future he can help with little tweeks and changes. We have no problem getting "Nerds" college/high school kids will jump at the opportunity to show their skills, however I'm unsure how we will get a solid following of people needing our services. So that's where we are at right now, how do we make it take off. 
Ian -  
Thank you for the positive feedback in a very negative world I really appreciate it! 
Dharmesh - 
Great post by the way, words can't explain the way your story relates to my life.

posted on Tuesday, March 24, 2009 at 9:28 AM by Michael Klear

The number one thing to remember is: 
No matter what they tell you at your seminars, or what your fake friends on Twitter who have no job say... Work is hard, and if it's not, then it's not work (by work, I mean it's gonna make you money). It can be fun too, but fun like running a marathon, not like having a water balloon fight while taping the next "girls gone wild". 
If people in this country understood that better, and were willing to put as much effort into doing work as they do looking for the next trick, our economy wouldn't be in the toilet. 
Get 8 hours of work done, and when you finish those 8 hours do 8 more just in case you get sick tomorrow. That's how you become successful. 
The thing that sets the rich apart from the poor is what they do in their spare time 
- Albert Einstein

posted on Tuesday, March 24, 2009 at 6:25 PM by mikemike

When you've released a product, and its not quite burning up the track, I've found defining high level goals for the entire company help decide what you should do. Let's say that the goal is "sell to 5 customers" - then it becomes easier to prioritize integrating a billing system over tweaking the site design. Breaking the high level company goals into more concrete goals also helps - for instance, "sign up 5 customers" could translate to "start an SEM campaign", "determine what kind of customers to target", "create target customer list", etc. 
Great post, btw - I can empathize with the problem completely, and I feel that the framework for prioritizing is a very good start. Got me thinking about how to change how we prioritize at my startup. 

posted on Wednesday, March 25, 2009 at 4:46 AM by Vijay R

Dharmesh - Great post!! 
You make things so clear. You are an inspiration.  
Thanks, keep it up. 

posted on Wednesday, March 25, 2009 at 5:27 PM by MOT

Dharmesh, some fantastic points here. 
I think if you talked to lots of successful entreprenuers you'd find that most have this kind of prioritization skill built-in. The good news is that this can be learned for those of us who weren't born with it!

posted on Wednesday, March 25, 2009 at 6:18 PM by Dan Abdinoor

3am... 3am... what am I doing at 3am? 
~ corporate widow 

posted on Wednesday, March 25, 2009 at 6:33 PM by Kirsten

Another great post. Been following for awhile but like you, I'm usually too busy to get on someone's website to leave a comment. But, you always say it like it is and I respect that. The truth is, it's fcking hard to do a solid product implementation on your own and knowing what do to next is tough b/c there's no one there to guide you/bounce ideas off/etc. So, I hear you man... 
Keep up the great work! Can't wait to ping with you a link to my product site on release. I'll definitely put good word out there about your blog and the real world, solid insights. 
Thanks again!

posted on Wednesday, March 25, 2009 at 8:13 PM by Chris

It was my pleasure to visit your Website. I am also very Website you enjoy the article.And I also have the feeling that it was really a pity that we didn’t meet each other earlier. Because the kindness and warmth in your blog can make me completely relaxed and happy. I hope that you will visit my blog too to see if you can have the same feeling. 

posted on Tuesday, March 31, 2009 at 2:19 AM by TiaoZao

Nice post. Prioritization and Focus can be very difficult, I use TOC's 5 focusing steps to help me find leverage in my task lists. Lots of projects don't always add the greatest return to the business, be weary of intertia and stay focused on what's key to moving the business forward.

posted on Tuesday, April 07, 2009 at 2:44 AM by Derek

I'm glad I found your site today, Dharmesh. This is *so* where I'm at right now in my startup. I was on track and had a plan - but the more I learn and read, the more conflicting advice I see and the more there is to do and decide. I feel very off-track. It's time to clear the clutter. Go back to the big picture, the bare bones, then start putting back the tasks/options that fit. Toss the rest. Now I'm talking to myself too!  
I like your suggestions for classifying each item. It will certainly help "sub-sort" them within the important/urgent/etc categories. I will build this in while I clutter-clear. Thanks! It's nice to meet you.

posted on Tuesday, April 07, 2009 at 6:28 PM by Deb

When deciding what to work on, we have to deal with income generation first. With no money, the business does not run. Then we can fix things that are broken. I see a lot of business owners waste time fixing what is not broken. 
Dr. Wright 
The Wright Place TV Show 

posted on Wednesday, April 08, 2009 at 6:18 AM by DR wright

Thank you for this. While I do keep "the list", I simply use the high, normal and low priority method. Which was fine until I noticed that almost 1/2 of the work that I wanted/needed to get done was in the 'high' bucket. There was just no way in hell that so many things were worthy of such a classification. I applied your simple criteria and it really helped to streamline my tactical goals to a point which I could execute on strategy without wanting to jump out the window... which would of itself be futile as my office is on the first floor ;-/

posted on Thursday, April 09, 2009 at 11:45 AM by Peter Bishop

Thanks for the article, I get paralysis seeing all the great ideas in various articles that I should do but just don't have time. At least this wasn't one of those articles.

posted on Sunday, April 12, 2009 at 3:14 PM by Paul

Great post! Very helpful!

posted on Wednesday, April 15, 2009 at 10:21 AM by Bina

This sounds like something i go through every morning--your not weird. I think one reason "the list" often reproduces itself faster than a rabbit population, is the fear that one of the ideas we get would of been the next million dollar deal if only we gave it some tender care and loving.  
I think its important to try and get some concrete statistics. I would recommend testing ideas out using some type of Analytics. Put your ideas on a website and see how people respond! you'll get a sense of which ones are worth pursuing and it'll put your worse nightmares of having eluded a "genius idea" to rest.

posted on Saturday, May 16, 2009 at 2:53 PM by Shirley Wang

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