When founders get the Sunday Scaries

Plus, everything due by April 15

I stood for nothing, so I fell for everything

A few weeks ago, a friend sent me an influencer video that was making the rounds. A woman had built a 7-figure business in the span of a couple of years. She followed all the online advice she could find. She followed scale techniques from expensive workshops and masterminds. She set up consulting, then group coaching, and eventually hired a team of people to feed the lead beast and deliver scaled programs.

And sure enough, she found herself grossing over $1 million a year.

She woke up one day and realized she hated all of it. She designed the company for a customer she didn’t want. She built a team for a company she didn’t want to run. She felt stuck in the scale trap.

So what did she do?

She shut the company down and took a year off. She let everyone go. She didn’t know who she was anymore or what she stood for.

Longtime readers know what I’m going to say next: if you follow someone else’s playbook, don’t be surprised when you wind up with someone else’s business. 

Around the same time, Forbes published a story entitled, “How to find a greater sense of purpose at work.” It started showing up on my LinkedIn and news feeds. The article cited several studies on what we need from our workplaces to show up every day and feel good about it. The quote that stuck with me was, “Finding purpose at work requires you to reflect on your values and clarify your priorities.” 

As a founder, if you want to build a company where YOU want to work, these need to be YOUR values and priorities. 

A centering principle will clarify what products or services are for you, which customers you want to serve, and what kind of employer or partner you want to be. All of that will inform your pricing and marketing strategy.

Most business planning processes focus on the customer and the market first. Is the market big enough? What’s the opportunity?

And that’s the alignment change. In my Business Design Bootcamp, I start by asking founders what matters to them beyond the money. Once we answer that question, it doesn’t take long for their choices to get really clear. This is for me, this is not for me. Less trial and error, more intentional direction. 

If you’re finding yourself with the Sunday Scaries about a company you’ve built, don’t throw it all away. Think about what matters to you and what you want your company to be. What would have to change? Start with that lens, and see how much clearer things become.

April Dates to Know

And thus, we leave the philosophical realm for a much more concrete one: it’s tax time. The date you need to know is April 15. Here’s a rundown of deadlines:

  • File 2023 federal and state income tax returns or extensions.

    • C Corporation and Fiduciary income tax returns

    • California single-member LLC income tax returns (and your $800 annual payment)

    • Individual returns

  • Make your final 2023 estimated tax payment. If you can’t pay in full, here’s a YouTube video from the IRS about payment plans. The payment deadline applies even if you take an extension for your return. Don’t skip filing just because you can’t pay. 

  • Contribute to personal and business retirement plans.

    • Personal 2023 Traditional and Roth IRA and HSA contributions must be received by April 15 or before you file your taxes. No extensions. 

    • Business SEP and 401k contributions are due by the time you file. If you are on extension, your contribution deadline is also extended.

  • Make your Q1 2024 estimated payment (January - March). Yes, it’s a double tax deadline! If you’re new to self-employment, or it’s the first time you’ll need to make estimated payments, check out this article on estimated tax payments, courtesy of my tax accountant. 

  • Check your state registrations. Many states require you to file an annual report between April 1 and May 1. 

One other date: April 11. Ask me anything, before you hit this deadline. Join me on Thursday, April 11 at 10 AM Pacific for our subscriber AMA. Use this Zoom link and remember to submit your questions! Live hot seat is always available. We’ll remind you on Thursday morning and a few minutes before we start. 

Media Kit 

TikTok ban in Senate. Will ByteDance be forced to divest its US TikTok operations? This week, the US Senate Commerce Committee will consider how to amend the House bill calling for divestiture of TikTok into a US entity on the basis of national security. (“Ban” in this case isn’t actually a shutdown, just a modification of ownership. Perhaps to the guy who made The Lego Movie.) ByteDance has relataliated by investing $2 million to advertise against pro-ban senators in five battleground states.

Organize your digital demise. While we often plan for who would inherit our company, our digital afterlife remains a critical but overlooked part of succession planning. Can someone access your bank account? Run your payroll? Let folks know what’s up on your social media channels? For most of us, that answer is no. On April 26, join AfterLight to learn the basics of organizing your digital estate plan. Register here

I’ll have that latte and avocado toast now. A new economic study from Ned Davis Research (NDR) shows that Millennial women are now the highest participating workforce group across 19 developed economies. Women aged 25-34 are more educated, have higher paying jobs, and in turn, are driving more economic growth than their male counterparts. One of the key facilitating factors? Hybrid and remote work.

Something else you wish I would have covered today? Hit reply, I’d love to have your suggestions. Or, let’s talk this week