What if you could get business advice from someone who understands your market, your customers, and your constraints better than any external advisor? Someone who knows exactly why you made certain decisions and what factors influenced your strategy? That person exists - it's you, from 30 days ago.
The concept is simple: when you're feeling clear about your business direction, you write an email to yourself that gets delivered a month later. Often, it arrives exactly when you're questioning those decisions or feeling uncertain about your path.
Running your own business can be lonely, especially when facing decisions that feel too important to get wrong. Everyone has opinions about what you should do, but most advice comes from people who don't understand your specific situation, market, or constraints.
As an entrepreneur, you're constantly making judgment calls with incomplete information. Should you pivot your product? Is this partnership worth pursuing? Are you focusing on the right metrics? These decisions feel crucial, but there's often no one who really understands all the factors involved.
Friends and family mean well, but they don't know your customers or your industry. Other entrepreneurs face different challenges in different markets. Even advisors and mentors are working with limited information about your day-to-day reality.
This isolation can lead to either paralysis or constant second-guessing. You make decisions, then immediately wonder if you chose correctly.
When you're feeling confident about your direction and have clarity about your decisions, you write to your future self about your current thinking. This gets delivered a month later, often when you're questioning those same decisions.
You're not trying to predict future problems or lock yourself into specific strategies. You're documenting your reasoning while it's fresh and based on current information.
Your current strategy and why. What are you focusing on right now, and what led you to this approach? Include the specific factors that influenced your decision - customer feedback, market research, financial constraints, or competitive pressures.
What you're seeing that others might miss. As someone who's deeply involved in your business, you notice things that outsiders don't. Maybe you're seeing early signs of market shifts, or you have insights about customer behavior that aren't obvious from the outside.
Lessons from recent experiences. What have you learned from recent wins and failures while the insights are still fresh? What worked better than expected? What failed in surprising ways?
Your reasoning behind major decisions. When you make significant choices about product direction, hiring, or market strategy, document your thought process. Future-you will benefit from understanding not just what you decided, but why.
A month later, you'll often be facing new uncertainties or questioning decisions you made earlier. The email provides perspective from past-you who was closer to the original reasoning and had different information available.
This can be particularly valuable when you're tempted to change course based on new concerns. Sometimes those concerns are valid and represent important new information. Other times, they're just the normal uncertainty that comes with running a business.
Reading your past reasoning helps you distinguish between legitimate reasons to pivot and temporary doubts that will pass.
Your past self didn't know what you know now. Market conditions change, new information emerges, and customer needs evolve. An email from a month ago might be completely irrelevant to your current situation.
The practice works best for maintaining consistency in your overall approach rather than making specific tactical decisions. Your past self can remind you why you chose your current direction, but they can't tell you whether that direction is still correct.
This tends to work well for entrepreneurs who are generally good at making decisions but struggle with the isolation and second-guessing that comes with running a business alone.
It's particularly useful for people who have clear strategic thinking when they're feeling confident but lose perspective during stressful periods. Reading their own reasoning during calmer moments can help them distinguish between valid concerns and temporary anxiety.
The practice is less helpful for entrepreneurs who struggle with basic decision-making or who genuinely need external input to see their blind spots. An email from yourself won't provide the outside perspective that comes from advisors, mentors, or peer groups.
This isn't a substitute for real feedback from customers, advisors, or other entrepreneurs. It's more like having a conversation with someone who knows your business intimately - because they are you, just from a slightly different moment in time.
The emails work best when you view them as one input among many rather than as definitive guidance. They provide continuity and perspective, but they shouldn't override new information or legitimate changes in circumstances.
Send an email to hello@dearme.email and we'll deliver it back to you in 30 days.
Send an email to future me