10/11/2014 05:08 GMT | Updated 07/01/2015 05:59 GMT

Five Things I Need to Know Right Now (as An Aspiring Entrepreneur)

The gap between the hindsight of successful entrepreneurs and the need-to-know of aspiring entrepreneurs is light years.

The gap between the hindsight of successful entrepreneurs and the need-to-know of aspiring entrepreneurs is light years.

Articles like 5 lessons I wish I knew as a young entrepreneur are frustratingly unhelpful.

I read them hoping for some rich or refreshing insight only to feel stunned by how out of touch they are.

I know how to say 'no'; I don't keep secrets; I don't pretend everything is ok; I realise that I'm a human with human needs; and I love meditation.

All valid and valuable tips for life in general, but not even close to what I wish I knew right know.

Just FYI: Not every aspiring entrepreneur is in their 20s, and not every 20-something needs spiritual advice.

In fact, more millennials meditate and practice yoga than any generation before them at the same age.

So let's say I've got all the woo stuff sorted.

Here's what I really want to know:

How do I generate an income while working on my signature product?

Yeah, this old chestnut. Faced with the constant threat of running out of cash, I've battled non-stop with the same old catch-22: get a short-term corporate contract and sacrifice time & energy on my project.

Yes, in 10 years time I won't care if I launched my project in October or March, but right now I do. Besides, everyone keeps telling me there are no jobs.

Do I forge ahead bravely putting everything I've got into this? Do I seek government startup funding or crowd source? Do I get a part-time retail job to pay the rent? Do I whip up some smaller products & services to sell short-term? Do I turn my current abode upside down in the hope that previous guests left cash in the sofa?

What do I need to consider to make the best decision for myself right now?

How do I manage my business admin as a location independent?

I can go where I want, I can fit everything I need in one bag, I can take a week off to explore when I arrive somewhere new, and I can fire up the laptop whenever I want. It's pretty darn perfect.

But not quite. Bank accounts, taxes, and mail are a headache. Banking & tax bodies require a residential address, and some credit card companies still send out mandatory paper statements. If you can find a willing family member or friend, do you trust them to open your mail and keep you up to date? I've missed tax-filing reminders and incurred fines.

I could register each foreign address and let my mail chase me around the world but there must be a better way.

The real question is this: if the way we live and work is changing why aren't systems keeping up with us?

How do I stop feeling guilty about working 3-5 hours a day?

I wrap up my workday in less than three hours knowing that I have completed my most important building-building task for the day.

I spend the rest of the day on the beach, practicing yoga, reading books and studying my heart out.

I care more about what I'm doing now than anything I've ever done, and my productivity is through the roof because I procrastinate less.

I don't have a to-do list because I get things done.

So why do I feel like I should be working more?

What should I outsource with my tiny budget?

The tiny business's path to success lies in outsourcing.

The question is, what should I outsource and how do I make sure I don't get screwed?

I could outsource everything outside of my zone of genius. But this would include almost everything implementation related. I'm a strategist and idea person after all. So what do I prioritise?

And how can I trust services and people that are cheap?

I could spend years searching for someone with the perfect set of skills & needs to barter with.

Does anyone out there have an outsourcing cheat sheet for bootstrapping newbies?

Ok, so maybe one troubling mental state:

How do I accept friends' decisions to stay in the corporate world?

I'm not talking about those who love it -- relish it -- and are in fact living their dream. There are many of those.

I'm not talking about those who have never uttered the desire to do anything else, or voiced the slightest curiosity of what else they could be doing with their time.

I'm talking about the friends with very real talents and dreams who are choosing to stay in jobs they loathe.

Friends who have gone for months accidentally unemployed and used their time to interview for another dozen jobs they will never love instead of seizing the opportunity to follow their passions.

Friends who are choosing to tow the line because they want a house and a car.

The obvious logic prevails: it's none of my damn business. But it's crushing.

How do I stand by and watch?

These are the real-time challenges we're facing as aspiring entrepreneurs. Real-time insight would be helpful.

And FYI: We're meditating on them already.


Stephanie Holland is a freedom-obsessed business strategist empowering purposeful millennials and corporate misfits to live & work with wild vision. You can find her at StephanieHolland.Co & @StephTHolland.