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Planning for the Worst, Hoping for the Best

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Stickers at the 8THIRTYFOUR office say, "This train has sailed" and "We are not assholes."

…and screaming in your car is totally normal.

Owning a small business is the fastest way to develop anxiety, insomnia, and a drinking habit you call “networking.”

I’ve been running 8THIRTYFOUR for 17 years, and I can tell you right now—this shit ain’t for the weak.

2008: Housing crash.
2020: Global pandemic.
2016–25: A political circus starring a walking lawsuit and a recession dressed in red, white, and “oops I deregulated that.”

And yet, here we are. Still standing. Still scrappy. Still screaming into the void (or into our pillows) and making payroll.

How? Because I don’t just hope things work out—I plan for when they don’t.

I Love Hope. I Just Don’t Trust It.

Hope is great. It’s nice for some people. It’s the Golden Retriever of emotions (I’m more of a Doberman). If that’s your strategy, you’re about to experience one hell of a ride.

Good businesses make it through the hard times because they plan like everything’s going to fall apart tomorrow—and then act like everything might just be okay.

I call it paranoia with purpose.

Four Exit Strategies and Iced Red Wine

I always have 2 to 4 courses of action in my back pocket – thank you ADHD. When things hit the fan, you don’t get to panic—you have to move. Fast.

I’m not talking about “Maybe we post more on social” or “Let’s try a webinar.” I’m talking about what actually keeps the business alive.

Get ready to find comfort in the uncomfortable.

Protect the business at all costs

You love your team. I love mine. But this is business, and when survival’s on the line, you have to prioritize the company over everything else. That means asking the awful questions:

  • Reevaluate your benefits and make temporary adjustments
  • Pause the IRA match
  • Reduce hours or cut salaries across the board
  • Lay someone off?
  • Cut subscriptions, pause vendor services

No one wants to do this. But pretending you can “culture” your way through a cash flow crisis is fantasy. Leadership means making the hard calls, and carrying the weight so your team doesn’t have to.

Show Up Louder

When everyone else is retreating, you have to double down on visibility. That’s not a suggestion—it’s a requirement. If no one knows you exist, you will not survive.

This is when marketing matters most:

  • Invest in public relations to stay top of mind and relevant. Lean into thought leadership—write, speak, share your story, take a stand
  • Don’t ghost. Post on social, provide value, record the podcast and help others be visible
  • Commit to digital marketing. Organic content + paid strategy = longevity, run those ads.

Your brand is your safety net. People don’t hire companies they can’t see, and they don’t stick with the ones that go silent when times get tough. You don’t need to be everywhere—but you do need to be visible, valuable, and very loud about what you do best.

Timing is Everything (and You’ll Still Second-Guess It)

There is no sign that says “ACT NOW.” Look at the following and then make your move.

  1. Data – Not vibes. Numbers. Revenue, margins, close rate, retention. If they dip, start prepping.
  2. Gut – Not to be confused with anxiety. Learn the difference. I’ve ignored my gut before. It cost me.
  3. Team feedback – If your team seems stressed, overwhelmed, or twitchy, it’s not just “Q2 energy.” Talk to them.
  4. Would I regret not doing this now? If the answer’s yes, there’s your answer.

And once you decide—rip the Band-Aid off – indecision is a killer.

You’re Not Alone (But It’ll Feel Like It)

Small business ownership is isolating as hell. We don’t have shareholders. We are the board. We don’t get to hide behind layers of management. We have to stand in the fire, smile during the team meeting, and then scream in our car at 6:42 p.m. after someone asked for “just one more revision.”

I see you. I am you.

Planning for the worst isn’t negativity. It’s leadership. It’s survival. It’s building something that outlasts the chaos, the politicians, the algorithms, and the toxic clients.

We don’t get to daydream. We get to fight.

Honestly? That’s kind of our thing.

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8THIRTYFOUR Skills Survival School

Kick off: September

90 Days  |  4 Sessions  |  5 Modules  |  6 Mentor Meetings

A cohort-based integrated learning program that builds professional skills through in-person training, eLearning, and mentorship. Multiple cohorts available.

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