Completing the Last Mile

One of the things I get asked about a lot is at what point do you know if you’re ready to take the plunge and start running your online business or freelancing gig full time.  People all want to know at what point they can cast off the shackles of their regular job and start enjoying the freedom of being their own boss.

The obvious caveat that I’d like to start with is that I’m one of the biggest advocates you’ll come across for side hustling.  I know, I know… It’s boring and not very adventurous, but I think it’s also the safer play much of the time.  For most people, going all in on their business is a move that puts their family’s financial stability at risk and five-year failure rate of startup businesses is astronomical.

But let’s put aside my own bias and dire warnings and talk about when you know.

I think there are a few financial metrics that we need to talk about first.

You need to have enough free cash flow in your business to sustain it for at least three months.  That means that in your business’ bank account, you should have enough unencumbered cash to last three months running the assumption that you get zero revenue for that entire period.

You’re probably thinking, “Wow, that’s absurd, I’m running a successful business, I’ve got income coming in all the time, why would I need a three-month cash buffer?”

There’s a bit of history and logic to this.

Most online business owners and freelancers get paid through PayPal and/or Stripe.  These companies can and do freeze your money.  I’ve lost count of the number of people over the years who I’ve seen PayPal just put a six-month, 100% rolling reserve on with no chance for appeal – literally, they hold your money for six months and then start paying it out to you daily.

More recently, the reserves they employ are a little less onerous: they can be 90-day rolling reserves of somewhere between 10% and 25% of your daily earning, minimum reserves of a set cash amount (often times $5000, but I’ve seen as high as $100,000) and a jumpstart reserve where they just take and hold a set amount of money indefinitely.

If you operate on 25% margins and PayPal institutes a 90 day, 25% rolling reserve, how much free cash will you be spinning off during that initial reserve period?

Yeah, zero… That’s why having that three-month buffer in unencumbered cash is critical as a safety net.

If you’re not familiar with the term “unencumbered”, it just means that the money isn’t spoken for or committed for another purpose.

The second metric that I think you should shoot for is a personal “reserve” fund in your bank account.  There are lots of names for this set of savings, but I like to consider it runway.

I think you should have six months of your current income stashed away in a separate “rainy day” bank account.  I’m not a financial advisor, but I’d also consider a rolling 30, 60 or 90-day term deposit because the money is “less” accessible and you get a higher rate of interest but in a pinch, it’s still liquid.

This kind of goes hand in glove with the first one – if something goes wrong that is outside of your control in the business and it stops spinning off an income for a month or two, you have this runway to fall back on.

The third metric is probably the most frequently looked at, “How much should you be making?”

Some people say that the income that you derive from your business should be able to directly replace your salary or job income.

I think that’s short-sighted and stupid.

Think about this logically… You’ve been building your business as a side hustle for a couple years, you’ve really turned it into something that looks sustainable, it’s turning a nice profit and your family is really reaping the benefit of that extra dosh every month.

See what happened there?

You’ve probably been treating that profit as EXTRA income so your lifestyle (and therefore your cost of living) have exceeded your salary or at the very least, you’d have to cut back on your lifestyle if suddenly your salary were to vanish.

That’s not ideal.

I tend to have a different set of metrics around this.

I’ve kind of come to the realization over the years that around $360k to $400k per year of income is an amount that is hard to spend for a normal person on a monthly basis.  If you work and don’t do anything stupid, that kind of money coming in every month is hard to go through.

So if your business is spinning off that kind of income, you should be good to go.

The other one that I tend to suggest to people is DOUBLE their annual salary.  Again, if your business is throwing off an income to you of double whatever your job is paying, you either have a crappy job or a good business… Or potentially both of those things are true.

Either way, those are the kind of numbers for most people.

If you’re on a very high salary, say $200k+ per year, these kinds of numbers get a bit funky and stop making sense.  At those numbers, you really need to be smart about your next moves because a $200k+ per year career is a pretty nice thing to have, especially if you’re in the US and get things like medical benefits, etc.

The last comment I want to make is an overarching statement.

Your business is an asset that you should be building.  The mentality I’ve always had is that “Sean Inc” is worth X and my job is to grow the value of that asset as much as I can for the long-term benefit of my family.

There will inevitably come a point where it may be better for your family’s long-term best interest for you to pack in the job and focus on growing the business asset because that’s the better decision.  This could revolve around financials, lifestyle or some combination of the two.

I think you should always be making these decisions in the context of what’s in the family’s best interests.  It’s also important to think about what those outcomes look like in advance so that you can plan for it accordingly rather than waking up one day and thinking that wearing pants every day is a pain and you’d like to skip that, so full-time in your business it is.

I call this planning the last mile.  It’s always the hardest and the one that seems to take the longest.  If you put the work in beforehand, it will be much easier to conquer when the time comes.

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