Stuff I’ve Learned About Running A Business #2: Ask for help. No, really, do it now.

Robin Cangie
4 min readMar 10, 2020
Photo by “My Life Through A Lens” on Unsplash

This is the second issue of my newsletter, Stuff I’ve Learned about Running a Business. You can view previous issues here.

TL;DR — No one is successful all on their own. Creating anything worthwhile is fucking hard, and it takes a village. So stop trying to do everything yourself. Swallow your pride and ask for the help you need.

When I first went into business for myself, I was terrified. That’s a laughable understatement. At night, I would lie awake wondering how I was going to make it work. By day, I did my best to hide it, which felt even worse.

I don’t know exactly why, but anyone who’s taken a big leap of faith can back me up on this. When you first start out, there’s a HUGE amount of pressure to look like you have your shit together. To look like it’s effortless. To look so competent, so sure of yourself, so totally, completely, undeniably successful, that no one will question whether or not you have what it takes.

Good Intentions and Awkward Questions

I think part of the problem is that most people don’t understand why you’d take a huge risk like that, nor what’s really involved in doing so. Why would you want to leave the security of a steady paycheck and benefits, especially if you have a good job? Why would you subject yourself to that much stress and hard work? Why would you open yourself up to the risk of failure?

It makes them uncomfortable. Then they project that discomfort onto you, usually in the form of very awkward, well-meaning questions like, “So, how’s your business going?” [Side note: Dear family and friends of new business owners, never, never, NEVER ask this question! You have no idea how much psychological misery you’re about to cause.]

When you first start out, there’s a HUGE amount of pressure to look like you have your shit together. To look like it’s effortless. To look so competent, so sure of yourself, so totally, completely, undeniably successful, that no one will question whether or not you have what it takes.

No one has their shit together at the beginning.

“So, how’s your business going?” I used to dread this question from my family and friends, because I knew what the answer was supposed to be. It was supposed to be, “Great! It’s going so great!” I was lying, of course.

Because any other answer would invite a slew of even more uncomfortable questions, or worse, unsolicited advice from people who had no idea what it actually takes (not to mention how long it takes — months if you’re lucky, but probably years) to build a successful business. So that’s the answer I gave.

But here is the hard truth: no one has their shit together at the beginning. Repeat after me: No one has their shit together at the beginning. Very few people ever really get their shit together, even the outwardly successful ones.

“So, how’s your business going?” I used to dread this question from my family and friends, because I knew what the answer was supposed to be. It was supposed to be, “Great! It’s going so great!” I was lying, of course.

Ask for help. No, really, do it now.

And that, dear readers, brings me to the actual point I was trying to make before I went off on a tangent about the harms of good intentions, which is that the whole pulling yourself up by your bootstraps thing is bullshit. Success does not occur in a vacuum. Everyone who succeeds had help. And that’s OK! Building anything worthwhile is fucking hard, and it takes a village.

Yes, a village. A village of people who believe in you, who want you to succeed, who are willing to help you get there on your terms. They are not the people who ask you, “So, how’s your business going?” They are the people who say, “I believe in you, and I want to help. Tell me what you need.”

So who is your village? Go ask them for help. Do it right now. I’m serious. There’s something you need. Go and ask for it. Don’t think you have a village? Search for them. I promise you, they’re out there. They’re in meetups and Twitter chats and Facebook groups and co-working spaces, and they’re ready and willing to help you.

Success does not occur in a vacuum. Everyone who succeeds had help. And that’s OK! Building anything worthwhile is fucking hard, and it takes a village.

You need them to help you. And lest you doubt, you are worthy of asking for and receiving help. Yes, you are. You are doing something brave and valuable and incredibly hard, and you can’t do it by yourself. No one can.

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Robin Cangie

I help B2B tech companies grow and scale their marketing. Learn more at https://robincangie.me