Automattic is a great company with an amazing vision and purpose. And two months ago I left.

There wasn't any crazy drama (although that would make this post more interesting). I simply wasn't working on things that excited me. And eventually I to got into a “good enough” slump and that left me drained. I missed that feeling you get after a solid day of work and you want to tell everyone the amazing things you're working on.

Work is such a big part of our lives and our identities and I didn't want that part to be unfulfilled.

I'm mostly writing this for myself but if you're thinking about leaving your job I hope it can provide guidance.

Should I Leave?

When you get into a slump your first thought might be to run away as fast as possible. But this is a mistake – everyone gets into slumps. Almost everything in life that's worth doing is hard.

The trick is strategic quitting. Seth Godin talks about this in his book The Dip:

Stick with the dips that are likely to pan out, quit the dips that aren't likely to pan out, and immediately quick the cul-de-sacs. The biggest obstacle to life is the inability to quit soon enough.

The thing about leaving is that I'll never know if I could have gotten out of that slump. And if you're thinking about it you have to accept that you'll never know. You just have to take your best guess.

I gave it several months but there wasn't any improvement so I made the choice to leave.

Can I Leave?

After you realize you want to leave you have to figure out if it's possible. And if it is possible what should I do? Work for myself or another company?

Balance Your Risk Portfolio

In Originals the author Adam Grant talks about risk portfolios. And how some of the most accomplished entrepreneurs of our generation didn't go all in. They made sure they had backup options:

• Steve Wozniak continued working for HP for a full year after the Apple 1 came out
• Henry Ford started his business while working for Thomas Edison – and he continued doing so for 2 years after inventing the carburetor
• Bill Gates applied for an official leave of absence before leaving university and had already started selling software his sophmore year
• The founders of Warby Parker had full time jobs lined up if their company failed

Grant argues that to be truly great you have to feel confident enough to try new things and still be safe if you fail.

For me this meant checking with my partner and talking about worst case scenarios. We do have a mortgage which has to be paid but apart from that and food we don't have a lot of risk. We don't have loans or kids. We decided that for both of us to feel safe I'd have to have six months of living expenses in the bank.

Having laid out our worst fears and knowing that we have backup options like my partners job, my friends, and my family removed the fear of failing. And that lack of fear is what let me take the leap to start my own thing.

If you have fear around failing because you need to pay the bills you might want to look into side gigs to supplement your income and remove some of that fear.

Reduce Your Expenses

The next part was painful.

I had to cut expenses – and when you work in tech you have the privilege of not having to worry about money too often.

I've been using Mint for years and it mostly just sits there. But at times like these it's so useful to look at my spending.

The first thing I had to do was look at my fixed costs. Things like my mortgage, health care, auto insurance, retirement, etc.

Here are mine:

• Mortgage – $1,400
• HOA – $300
• Renter's insurance – $25
• Electricity – $30
• Heat – $100
• Internet – $30
• Auto insurance – $80
• Auto gasoline & maintenance – $50
• Roth IRA contribution – $450
• Health insurance – $140
• Cell phone – $95
• Audible membership – $15

Wow that's a lot – and it adds up to $2,715. Now, my partner and I split bills so I actually pay just over $2,000. Still quite a bit.

But we're not done yet. Now we have to look at variable expenses. Things like groceries, shopping, etc. These are a bit harder to calculate but you can get an estimate of how much you pay for these over a period of 6 months with Mint.

• Groceries – $50
• Restaurants – $320
• Coffee shops – $150
• Clothing – $80

These add up to $600 a month. Now these numbers aren't perfect because it doesn't show how much my partner spends on groceries (which is typically her chore). But they're close enough.

We finally have a target – $2,600. But before we lock that in let's see if we can cut a few of those down.

I canceled my $95/mo plan with Sprint and got a super cheap phone & plan from Republic Wireless for $20 a month.

We committed to eating out less and eating in more more. And we're using a tool called Level that tracks our variable spending.

The Level widget on my iPad. I check it every morning to see how I'm doing budget wise.

For the past month restaurants is down to $180 and coffee shops is down to $50.

I also cut my clothing subscription from Bombfell. They send me something new every month instead of having to go shopping at the mall. I dislike shopping so when I have discretionary income I'll sign up for a service like Bombfell. But that's something that I can shut down temporarily. There's still a need to buy clothes obviously but it's not a monthly expense. And it's cheaper to get clothes myself.

So I've gone from $2,600 down to $2,300 a month. Still a chunk of money but much more reasonable.

What To Do With An Extra Room

I purchased a condo in April and I was looking forward to using the extra room as an office. But with recent developments it made sense to rethink that. A friend's lease was ending and he wanted to live downtown but couldn't afford a studio on his own.

Light bulb moment

He moved in and we split Mortgage + HOA three ways. It saves me another $300 a month.

Down to $2,000 a month to pay for all my fixed & variable expenses. That's a reasonable number to generate from a business. You still have to account for taxes and other things but it's at least in the ballpark.

Load Your Savings Account

While I was figuring out the roommate situation, figuring out how to switch cell phone companies, and refining my thoughts about what I could do on my own I started stock piling all my money into my savings account.

I cut way back on restaurants, movies, holidays, etc. And in 4 months I was able to double what I had in my savings account. I turned $10,000 into $20,000.

That gives me 10 months to figure out what I'm going to do with my business.

What Am I Going to Do?

This is actually a massive question and worth it's own blog post. For right now I'll just say that ever since I moved into the WordPress space I've been playing with different projects and different business models.

And I learned a lot about different models and how they work for me.

I have a desire to make my own products and to help small businesses. So it made the most sense to turn my existing e-commerce knowlege into online courses that others could consume.

I already put out two courses on Lynda.com:

• WordPress: Customizing WooCommerce Themes
• Learn Shopify: The Basics

And I have two more in the works.

The one downside with courses is that they take months to put together, they take a week to record, and they take weeks of post production. To bride the gap I plan on doing client work until I could get my own products up and running.

Profit First

One of the most useful books I read was about accounting. Sounds boring right?

It's actually great.

In Profit First Mike Michalowicz shows the importance of building systems around how you receive money and how you send it out.

Profitability isn't an event. It's a habit.

Most business owners put their money into one bank account and if they need to spend money on something they just spend it. If they have any left over then it's profit. But if they don't then they just need to work harder.

If you can't pay for your expenses that means you can't afford them. Don't take money from the profit bucket.

Mike suggests taking profit out first. And limiting your expenses each month to whatever is in your expense account. This way it's not about making more but about being smart with the money you have. It's a very simple system but one that I recommend every entrepreneur read before starting their own business.

How do I Leave?

Once I cut my expenses, planned how to bring in revenue, and setup my profit first system I was ready to leave. Now I just had to tell my employer.

Automattic hosts multiple meetups a year and since they're paying for the travel it's only fair to give them advanced notice. I gave them a month of notice and here I am two months after leaving my job – figuring out this whole entrepreneurial thing.

I haven't made buku bucks nor have I changed the world (yet). But I do believe that all of that can still happen. Life is a marathon not a sprint. And I plan on building this business carefully and for the long haul.