For some reason, recently, destiny seemingly started to deliver on a long-forgotten childhood dream of mine.

When I was a kid I was an avid reader. I consumed more books before age 10 than I probably have in all my adulthood. The resulting dream: being a writer.

20+ years later, all of a sudden, I found myself getting numerous offers for writing contracts. It made me think, wow, was the dream of writing I had my life’s purpose wanting to manifest?

Could it be? Me, a writer? Sure, I blog. But I’ve already discovered that for me, writing is a hobby, and I don’t find doing it for money all that enjoyable.

Nevertheless, I was asked to work on a project I felt passionate about, and the pay didn’t seem bad, so I agreed.

So ensued the wake-up call. Sadly, after doing the work I did not get paid on time. I had to make the decision to self-publish the work I’d done to retain my rights to it. Out went the promise of being part of an exciting new initiative, potentially more recognition, and progression as a blogger.

After making multiple attempts to collect payment and then notifying the other party that I was ending our relationship, I eventually received an offer for payment. But it was too late. I’d already pulled the trigger. I’m not the kind of person to tell someone I’m done working with them and change my mind. When I say I’m done, I’m not playing around.

I learned a couple of things here. For one, I learned that sometimes it’s necessary to ask for payment up front and if a prospective client doesn’t like it, it’s not worth the risk.

That was a no-brainer.

I also learned something about myself. Not only do I love writing on my own terms, but I also learned I’m not one to let someone else call all the shots – no matter what they promise.

I’m an enterprising person, and my goal is not to put myself out there to be nice. I’m putting myself out there to get paid.

Shallow? I don’t think so. I have a family. Dreams alone aren’t going to take care of their needs or mine. I never would have said this out loud to anyone in the past, but now, it’s my mantra.

It’s been a long road but over time, I’ve slowly shed most of my naiveté.

Almost 4 years ago, I left a comfortable but unpromising corporate job, and I have learned a lot about the world since then.

Sure, being in that job helped me develop in lots of different ways, but I was sheltered. Many of the skills I had were underdeveloped, and there was no way I would have discovered this until I started anew.

I’ve gone through a lot just to get re-started. I have dealt with cutthroat characters and straight up thieves, balancing my need for work and my need for getting established with ensuring I’m decently compensated. At times, I’ve suffered not being compensated at all by shady clients that didn’t keep their promises.

I’ve also learned there are some decent, honest people in this world. I wish I could know who they are in all situations within an instant, but without major red flags, it seems to require going through the test of time.

Knowing a little more about business than I ever wanted to know, I’ve learned that no matter how much I want to, I can’t know or do everything.

That means to fly solo and be good, I need good support. Meaning, I have to allocate some resources to investing in decent tools and hiring experts. Honestly, “flying solo” is a saying that doesn’t live up to its own ideals.

I am not a shadowy figure behind a desk that haphazardly does work for growing companies. I need to show up with my best face on, and do the best possible job I can, as consistently as possible.

Compromising for anything less would substantially lower my quality of life. Working this way isn’t easy, but I do feel that it’s better. Everything comes at a cost.

I’m still learning every day, so in no way is this post meant to portray that I’ve got it all figured out.

Here are some things I’m still working on, and if you’re an enterprising person you may be able to relate, get some ideas, or make some suggestions based on your own journey.

1. You’re too small to use mediocre tools.

Automate everything you can with the best possible tools you can afford. If you are wasting time with manual tasks, progress will be really hard. You can’t afford to automate, you say? If you value your time and want to increase your income, you can’t afford not to.

2. You should know how to collect money.

Collectors can be jerks. We all know this. But if you work and never cash in on your invoices, you’re not actually working.

3. There is no collaboration worthy of not getting paid.

Almost every person that is just getting started will at some point be offered an opportunity where they get to show what they can do, but without compensation. The exposure that’s promised may or may not come and hey, exposure doesn’t pay for things at the grocery store. Unless there’s a real measurable benefit, try to get paid for your participation. Doing work for free only cheapens your value.

4. You need sales training.

Like collectors, people often loathe salespeople. But without selling, your services won’t be known to anyone and you won’t make money. If you think selling is sleazy, get some training and you’ll learn there’s an ethical way to go about it.

5. Staying on top of trends is not just for teenagers.

To be competitive, you need to be relevant. Staying on top of a variety of current trends from tech, finance, workforce, even pop culture is necessary to ensure that you to can relate to the people you will engage with for the purpose of generating income.

6. You need a strong personal brand.

Usually, this is done using social media or a website and in general, your personal brand will be portrayed through your online presence. By visiting your social media pages on sites such as LinkedIn, Twitter, Instagram, and SnapChat, people should be able to gain a clear understanding of what you represent.

7. Strike a balance between being personal and being a professional.

Without people, there is no business. While people are now accustomed to doing business with robots, there are many transactions that still require a human touch. Leave the robotic behavior to the machines and interact with your colleagues like a human being. At the same time, don’t get too comfortable and make potential mistakes like disclosing inappropriate information, getting drunk at professional get-togethers, or doing work on a handshake when you know you should have a signed contract.

8. You need to know tax law.

This is tricky, but if you don’t want to get in trouble with the IRS while managing your finances in the way that saves you the most money, you should stay abreast of tax law. You don’t need to be able to quote every amendment that rolls out but you should understand the implications of those that affect you. This is time-consuming and confusing, so in addition to your own research, you should retain and consult qualified professionals. e.g., a good CPA to support you in your planning.

9. Be on your own payroll.

I’m not going to tell you that every freelancer should have an LLC, and I definitely won’t get into pros and cons of being a sole proprietor vs. working under an SCorp, but some research on this topic to make an informed decision will serve you well. And as part of understanding tax law, researching this topic will help you to save money, stay organized, and stay out of trouble with the IRS.

10. You can’t make money alone.

I know, I said this already, kind of. But as an oddly extroverted introvert and a remote worker, I know that sometimes, there are some of us that start having way too much fun by ourselves. People are pack animals and we need our relationships to do good for ourselves and others. It’s cool to like yourself but if you like your own company’s way more than you like everyone else’s, you will starve.

11. If you are lazy, you will starve.

Yep. I said that. If you want to skate by doing the bare minimum it will catch up with you. You can’t be lazy and enterprising. There might not be anyone around to see that you’re taking a nap during working hours, but if you don’t wake up, you’ll run out of resources, quick.

12. If you are fearful, you will starve.

Worried about what people think of you? Can’t talk to strangers? Afraid to travel or try new things? For the most part, all of this will work against you in an entrepreneurial situation.

13. Technical skills are a must.

Yes, automate everything that you can but even the process of implementing automation will require you to dig in just a bit. Being hands-on will also help increase your self-sufficiency.

14. If you behave ethically, you’ll avoid all kinds of nightmares.

Lying, stealing, cheating– this kind of nonsense catches up to everyone that participates in it. Follow The Golden Rule and you’ll be able to sleep at night.

15. Be aggressive, but not too aggressive.

Your passion for what you do needs to drive you away from complacency every day. Be aggressive in the energy that you put forth toward your goal, but not toward other people.

16. You’re going to fail.

I shed a few tears when I first started on this journey. I guess I thought I was a little more awesome than I actually was and indeed, I got shaken up just a few times. It didn’t take me long to stop being a crybaby, though, when I realized that as long as I’m going for improvement I’m going to get rejected and I’m going to fail. Sometimes, more often than I like. Accepting this as normal makes it easy for me to keep going and less likely that I’ll waste energy feeling sorry for myself. I don’t wish that you fail but I wish that you embrace every hiccup as a lesson. That’s what enterprising people do.

17. That math you learned in elementary school is important.

You may not need calculus, but you do need to understand the relevance of numbers and their impact in circumstances of both cause an effect. Math is a meaningful universal language that should be a major part of decision making. Be logical and have the basic operations, addition, subtraction, multiplication, and division, down pat.

18. So is reading comprehension.

Being able to recognize words is good, understanding their meanings is another. When doing business, you operate most effectively when your mind properly deciphers the instructions, messages, and written communications that you interact with every day.

19. Politics are important.

I keep talking about the relevance of people, and the subject of politics is another important facet. Who are your friends and inevitably who are your enemies? You can’t be everything to everybody, but you should know when to be what and to who.

20. You will need to continuously, strategically plan.

All of the above will help you to know what direction you need to head in, what steps to take, form appropriate expectations, and plan your goals.

As an enterprising person, there are going to be times you to feel like you’re flying by the seat of your pants, like you’re not sure what you should do next, and whether you’re even close to the doing the right thing at all.

You’ll need to regroup, you’ll need to make adjustments, and most of all, your love for the game will be what you need to keep you going.





