Sometimes exploration is worth it. Sometimes you just spent a week of the team’s attention answering a question the founder could have tested in an afternoon. That is the part I think leaders underestimate. Ideas do not only cost money. They cost time, focus, and brainpower long before anyone approves a budget. The question I’d want answered is: how much of the organization does this idea deserve yet?
Read MoreThe fear of success doesn't usually announce itself as fear. It sounds like planning. It sounds like due diligence. It sounds like being responsible.
What it actually is: A limiting belief. It’s spending today's energy on problems you'll only face if you win
Read MoreMost founders built their business from nothing. They were the product, the salesperson, the decision-maker, the culture. The company exists because they willed it into being. Somewhere along the way, being needed became part of who they are. That's not ego in the pejorative sense. It's human. We find meaning in being useful, in being the person others turn to.
Read MoreHere’s what I’ve noticed about the leaders who wait. They’re not unaware. They’re not ignoring obvious problems. They see them. They just learn to live with them. Margins tightening a little each quarter. A team dynamic that feels slightly off. A process that’s inefficient, but still works. None of it is broken enough to force action. So it waits. And while it waits, it becomes the new normal.
Read MoreEmotionally, walking away from a past loss feels worse than risking a future one. Psychologists call this loss aversion. People feel losses more intensely than equivalent gains. A million-dollar loss feels catastrophic in a way a potential million-dollar gain never will. That is why leaders keep pouring resources into failing projects.
Read MoreFounder mode is neither good nor bad. Hustle is neither noble nor toxic. The real question is simpler and harder. Is the urgency coming from the needs of the business, or from the wiring of the founder? I see this constantly. Founders who built successful companies and cannot break through the next level of growth. Not because they stopped working hard, but because they never stopped working the same way.
Read MoreMost leaders I work with dread annual planning. Not because planning is useless. Because everyone has an opinion on how you should do it. None of them run your business. And you’re stuck trying to satisfy everyone else’s version of “the right way” instead of figuring out what actually works for you. That’s the first problem.
Read MoreWhen you waffle, you're not avoiding a choice. You're making one. You're choosing to stay stuck. You're choosing to slow your team. You're choosing to let opportunities expire. Most of the time, the facts that informed your original decision haven't changed. Only your emotions have. Make the decision or don't. Stop pretending indecision is neutral.
For a while, businesses may be able to rely on word-of-mouth referrals and lots of networking. In the early days, it’s often necessary. The problem is that it doesn’t scale. What you’re missing when you don’t have a sales strategy…
Read MoreOne of the most frequent struggles I see with entrepreneurs and business owners is this tension between managing the day-to-day operations of the organization and focusing on overarching strategy. Many business owners who seek coaching or peer advisory boards know they’re not spending enough time on strategy, and they can’t figure out how to shift the balance.
Read MoreIf you’re in business long enough, one thing is inevitable. At some point, you’ll need to raise your prices. Business owners are often afraid of making that change, worried their customers will leave and revenues actually decline. The truth is, customers can weather difficult changes when businesses approach the issue with the customers’ needs in mind.
Read MoreAny successful business that’s been around for more than a few years has found themselves on that plateau, trying to figure out why their growth stalled or why they feel stuck. The plateau itself isn’t a problem. In fact, it may create an opportunity to look at your business, your product, or your market through new eyes.
Read MoreStartups and Small Businesses sometimes find themselves at the edge of a chasm. With success in developing and growing their business, a stage is reached where they find that the "next step" is a big one! Trajectify partners with the entrepreneur to build momentum and trajectory to be able to cross the chasm.
We offer private and group (Mastermind) coaching and hold frequent events and seminars.
Trajectify is founded my Mike Krupit, veteran of eight startups. Mike has helped dozens of companies grow and mentored and advised hundreds more.
I’ve been facilitating CEO peer groups for fifteen years. The biggest factor in whether someone gets value from a group is vulnerability. Not performative vulnerability. The kind that costs you something to say out loud, the thing you'd rather not say because it makes you look uncertain, stuck, bored, scared, or wrong. The people who get the most from these groups aren't necessarily the ones with the biggest problems. They're the ones willing to let the room see the problem clearly enough to help.
I don't think every CEO needs to become a LinkedIn personality. The question is simpler. Who needs to know you exist? Where are they? And what would help them understand how you think before they ever sit across from you? That answer will change as the company grows, as your buyers change, as platforms come and go. You adjust. That I don’t think you can do anymore is decide visibility isn’t part of your job at all. Your personal brand is important to your company’s brand.
Most founders and executives I work with are uncomfortable talking about how they look. It feels shallow. Not the point. I get it. They started their companies because of a vision, not an ego. By the time they're working with an advisor, they're wrestling with real problems: who belongs in which seats, how to build accountability, how to run a leadership meeting. Thinking about personal image can feel self-indulgent by comparison.
Founders tend to think about a major transition as a singular event. You prepare, announce, close, and now you're a different company. In my experience, the company starts changing well before any of that happens. I've been through this several times now, and the details were different every time. The weirdness was pretty consistent.
Sometimes exploration is worth it. Sometimes you just spent a week of the team’s attention answering a question the founder could have tested in an afternoon. That is the part I think leaders underestimate. Ideas do not only cost money. They cost time, focus, and brainpower long before anyone approves a budget. The question I’d want answered is: how much of the organization does this idea deserve yet?
Ask a room of leaders why they set goals and most will say accountability. That answer creates the problem. Goals exist for alignment. The company needs to reach a number, so this group does this, that group does that, and together the math works. Everyone is pointed in the same direction. Focus comes second. A good goal tells you what to say no to.
The instinct to build a team that moved in the same direction, at the same pace, with the same set of perspectives is limiting. Consistency is created at the expense of range. The goal isn't alignment of strengths. It's coverage. The most dangerous teams I've seen weren't the ones with conflict. hey were the ones with none. Where every conversation ends in agreement. Where nothing gets surfaced. Where the people who see things differently may have learned to stop saying so.
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Technology used to be expensive to build, and relatively inexpensive labor was often the better return. AI has changed that calculation for certain kinds of work. Tasks that once required entire teams can now be automated relatively cheaply. I don’t think CEOs should pretend otherwise. I do think they need to be honest about what actually changed.