Two Weeks on the Outside

The Journey Ahead

I knew starting out on my own wasn’t going to be glamourous. I knew that. It turns out it’s even less glamorous than I thought.

Maybe I’m just not doing it right, but the “hustling” I’ve been doing hasn’t felt like the hustlers of lore. That is to say, I don’t feel like a well-dressed, ex-collegiate lacrosse player who zips around town and signs deals over cocktails.

My typical day consists of me emailing people from my house, in sweats and a hoodie. Or riding my dilapidated bicycle 30 minutes across town to talk to someone for 60 minute about what they struggle with at work. Sometimes I meet people at coffee shops, but I never buy anything because I need to save money.

So it feels more like being a poor therapist with a nice computer, and I fucking love it. If you’re thinking of starting out on your own, here are a few tips that have helped me so far:

1. Learn to Say No.

I originally had this as #4, but it deserves to be near the top of the list. I’ve already written about how to say no effectively and highly recommend picking up that skill. Knowing how to say no to people, expenses and yourself will help you stay focused and disciplined.

2. Practice Lean Before Living It.

This was a tip I got from the guys at Wistia and probably the one I’m most fortunate to have put into practice. It’s no secret that your runway will be longer if you can get by with less, but doing that isn’t simple. The best thing to do is to start early and cut back (aggressively) over a period of time.

This gets easier as you start seeing gains. In the beginning, a $5 cup of coffee might seem like a trivial amount of money, but it becomes a larger percentage of your burn rate as you cut back. Knowing how to frame your expenses will help you make the right decisions.

Some cost-saving tips:

  • Make a batch of steel-cut oats. They’re delicious, keep well and are a great breakfast choice.
  • Buy a big bag of coffee beans and a French press. You can grind beans at your local grocery if you don’t own a grinder.
  • Invest in dry meat alternatives, like beans and chick peas.
  • Bake. It’s easy, involves less active time than cooking and can satisfy your sugary cravings.

Some things to try:

  • Savory pies, like Shepard’s pie, chicken pot pie, etc.
  • Chick pea salads.
  • Steel-cut oats, honey and raisins/nuts.

3. Master the Art of the Freebie.

Now is the time to reach out to your network or hack services to get the best deals. This is your livelihood on the line, and if you want to survive, then there’s no room for meekness.

A couple of tips:

Host your marketing site on Github Pages.

I prefer Github over Heroku because it’s super fast, and the code ends up there anyway. You can use it with Brunch, Jekyll or anything that compiles to static HTML/JS. As a front-end dev, I’m partial to it since it lets me work quickly and comfortably.

Find a Google Apps account.

Google Apps for Business is pretty awesome, but it was even more awesome when it was free. If you have one, start using it. If you don’t, find someone who wouldn’t mind gifting you theirs, or at least adding you as a sub-organization. Having a proper domain for email, documents AND the ability to spin up new email addresses is clutch.

Sign up for a free account(s).

Unbeknownst to some, AWS gives a free year of light-weight service for new sign ups. If you’ve already signed up in the past, use a new email address (this is where having a Google Apps account helps). Freemium was invented for just this reason, so use it to get the services you need.

Leverage your network.

If you know someone who works at an Apple store, ask them if they’ll use their discount on you. Odds are you have friends who work for product companies and can get you deals on business cards, hosting, software, etc. Now is the time.

4. Get an At-Home Hobby.

You no longer have the lunch room or water cooler to re-energize, so find something at home you can do to supplement that. Not having some way to break up your day will make you want to work from coffee shops or co-working spaces, which gets expensive and makes you more likely to buy things you don’t need.

I’ve been experimenting with infused cold-brew coffee at home. It’s both convenient and productive, because I need to make coffee anyway, and a French press holds enough cold brew for two servings. I have a bottling kit from when I tried beer brewing, so I make a batch for tomorrow and bottle one for a rainy day. It works out great and is a nice break.