Founders Need to Ask for Help - Even Though It's Terrifying

As an entrepreneur, asking for help is hard. It’s also scary.

We live in an age where we are bombarded by the highlight reels of others - our peers, our role models, our perceived rivals. In many ways, social media simply represents platforms that enable mass manipulation, the chance to weave a narrative that is surely partially true, but rarely, if ever, tells the whole story.

Each person’s whole story is messy. It is riddled with failures and losses and disappointments. Even when the greater arc is one of beauty, triumph, and success, there are, undoubtedly, the periods of doubt, shame, and straight-up pain that go left unsaid.

The lucky among us have close friends or family that we can turn to when things are tough, but often times, given our busy schedules and the desire to not concern our inner circle, we assure them that we’re okay!

We’re fine! Everything’s good!

Even when it’s not.

As an entrepreneur or a leader at a startup, you’ve had to take risks that others doubted. So you don’t want to admit that anything is less than rosy. You don’t want to feel forced to defend your decisions. You don’t want to face that this thing is harder and scarier than maybe you thought it would be.

You know people doubted you. And you set out to prove them wrong.

But now, you’re facing doubt.

You don’t need someone else to pile on or make you feel like you were an idiot to go down this path. And all too often, our friends just don’t get it. They don’t understand why you’ve decided to make less money for more work for the long shot hope of making it big.

Admitting that things are not good, that we’re struggling, that we need help feels like an intimidating prospect.

It feels like it will mar our good name, harm our reputation as a person with their proverbial shit together that we’ve worked so hard to earn.

We become convinced that we can muddle through this one alone. We just need to work a little harder, put our head down and get through it all.

And when we read the stories of our idols, our role models, there are few if any that describe their moments of reaching out for help, of owning their struggle, and asking for support and assistance.

No, these stories usually position them as a lone wolf or some transcendent leader - able to rally the troops and lead the charge to victory.

It is all too rare to read a story of when today's multi-millionaire sobbed on the floor of his bathroom, absolutely positive that his world, his business, and his reputation were about to crumble.

Or to hear from that successful entrepreneur about the times when she had to put payroll on her credit card because a client didn’t pay their invoice or a partner fell short of their promises.

Yes, people talk about the fact that business is hard. We know this.

But we don’t always know how or why.

We aren’t told what entrepreneurship feels like when it’s hard. So when it’s hard for us, the experience can feel isolating and lonely.

Recently I experienced a major business setback. It’s one that I can’t speak about publicly, but man, did it throw me for a loop. And I felt so alone going through it. So utterly alone.

And that loneliness, the weight of it, was overwhelming.

I felt ashamed that I’d found myself in such a position. And in many ways, my instinct was to retreat. To climb into my turtle shell and ignore the world outside until the storm had passed.

I am so glad I didn’t listen to this instinct.

Instead, I made phone calls. I sent emails. I tweeted raw and honest thoughts about needing help, needing an outside perspective, and well, needing encouragement.

And you know what?

I got it. In spades.

Frankly, the response of support, encouragement, and empathy floored me.

Even people I don’t know all that well offered words of kindness and support, to make recommendations of therapists and coaches, to just be kind.

Over and over again, they reminded me that I wasn’t alone - that I had more support than I had anticipated and that my situation wasn’t unique. They’d been through something similar or their friend had.

The result was this sense that I was right where I needed to be and that I would make it out in due time.

startup founders help support

how to ask for help when you’re going through something tough

  1. Ask a mentor for a call. Send that text. Shoot off that email. Just ask for 15 minutes. And come prepared with questions. Share your dilemma and ask for feedback. You’ll get it. Along with a lot of other advice and support. Be succinct, but be honest. No sugar coating.

  2. Have a meal with friends. Did you know that eating a meal with friends is the activity that statistically speaking has the largest positive impact on your happiness? Sometimes just communing over a meal and feeling a little less alone can make all the difference.

  3. Connect over coffee. I know it can be tough to put yourself out there when you’re feeling low, but sometimes connecting with someone new can be a reminder that all things will be okay. Find someone you think is interesting on LinkedIn and ask for a coffee or a call. Get to know someone new.

  4. Find a therapist. I think everyone should have a therapist and a coach. You need a neutral third party to bounce ideas off of and talk through hard things with. Prioritize this. Find your person.

The moral of the story? Ask for help.

You’ll be amazed by how readily people give it and how much better you feel with it.

And if there’s ever anything I can do - don’t hesitate to send me a LinkedIn message, @ me on twitter, or just comment below. We’re all in this together. Don’t forget that.