Many executives haven't run a real job search in twenty years. I mean, it’s pretty obvious life has been busy with things like running a company, leading teams across three continents, integrating acquisitions, making payroll, raising children, and doing almost everything except figuring out the new secret recipe for winning exposure on LinkedIn.
Other new RPA clients know where they want to go but don't have the network to get there. Some simply need more horsepower: another brain in the room, more hands, or someone who knows the market well enough to say, “Don’t spend an hour doing that. Do this instead.” That’s our job: we show up, we think, we introduce, we experiment, and when something isn’t working, we change it.
Occasionally though, something fascinating happens. Someone pays us thousands of dollars, listens carefully to everything we recommend, and does almost none of it. Not because they’re lazy, and not because they’re incapable. They doubt the strategy, the market, the introduction, whether anyone will respond, whether trying something new will make any difference. Eventually, underneath all of it, is this:
They doubt themselves. And doubt is a corroding element of anything positive and productive.
Here’s something I’ve learned about self-esteem: it behaves less like a feeling and more like a repository that you access. You build it one promise kept to yourself at a time.
You said you’d make the call, and you made it. You said you’d send five thoughtful messages, and you sent them. You said you’d walk into the room where you knew absolutely no one, and you went. None of these things are particularly impressive on their own, but add 'em up, and they become the foundation for a successful job search or a successful life.
Ever heard of this self-fulfilling prophecy - contempt prior to investigation? We decide something won’t work before we’ve actually tried it. Executives can be particularly talented at this. Success gives you judgment, experience, and pattern recognition. It can also give you the dangerous assumption that because you understood your last business, you automatically understand an entirely different business or will know the magic job-finding recipe when you hear it.
I’ve watched enormously accomplished people dismiss a networking strategy they’ve never tried, or write off an introduction before the other person has even received it.
Brené Brown talks about this beautifully in Dare to Lead. Courage isn’t the absence of fear; it’s moving forward in spite of the fear. The problem is the armor we put on: perfectionism, control, needing to be right, and being in a job search will activate every piece of armor you’ve got, because it requires uncertainty: asking, trying, being ignored, trying again, and occasionally looking a little foolish.
You don’t need to feel confident before sending the message. Send it anyway, and now you have evidence. Do it again tomorrow, and now you have a record.
Doubt has obvious signs. Requiring proof before you’ll act, wanting someone, anyone to tell you that the message will work before you send it, wanting proof the introduction will lead somewhere before you accept it.
You make allegations that the discomfort that you feel is your bad search, bad strategy. “This feels awkward” and “this doesn’t work” are not the same sentence.
You renegotiate promises with yourself. Monday: ten outreach messages this week. Wednesday: five thoughtful conversations is probably more strategic. Friday: next week is actually better timing.
Three Ways to Start Again
1. Stop asking, “Will this work?” Ask, “What could I learn if I try it?” You don’t need certainty to experiment. You need curiosity: try, learn, adjust. That’s how businesses innovate, how we’re learning to work with AI, and how good job searches work.
2. You cannot control whether the CEO replies, whether the recruiter calls, or whether the company eliminates the position after seven interviews and a personality assessment that made you question your childhood. You can control whether you did what you said you’d do. Five messages promised? Send five.
3. Borrow some confidence. You aren’t supposed to know everything. Borrow confidence from an advisor, a friend, a former colleague, a spouse, a mentor, or a near stranger who says, “I know someone you should meet.” And, for me, faith.
“Trust in the Lord with all your heart and lean not on your own understanding.” — Proverbs 3:5
That verse gets more interesting the older I get, because I would really prefer to understand things before I surrender the outcome. I’d like the plan, the timing, preferably a spreadsheet, and some assurances about the ending. Sometimes faith is much more practical: make the call, send the note, ask for help, keep the promise. Then get up tomorrow and do it again.
When someone hires us, I don’t expect them to arrive overflowing with confidence. If they knew exactly what to do, they probably wouldn’t need us. I expect questions. I expect bad days. I expect the occasional, “Terri, are you sure about this?”
What I don’t want is doubt quietly becoming the decision-maker. Chanting affirmations while refreshing LinkedIn was never the goal. Becoming someone you trust is. Becoming someone who has enough evidence to say:
I do hard things.
I can ask for help.
I’ve survived rejection.
I’ve changed direction.
I’ve shown up when I didn’t feel like showing up.
I kept my word to myself.
That’s where confidence comes from. A record, built one ordinary Tuesday at a time.
And if you’ve made enough small deposits over enough ordinary Tuesdays, something magical happens: when the big moment finally comes, you don’t have to manufacture belief in yourself. You’ve already earned it.
Collect the interest.
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