Career, Retirement, or Something in Between

You may be bored with your job and searching for more meaning. Perhaps you long to become an entrepreneur to express your passion and vision.

One of my favorite mentors, Mark Silver, has given me permission to post his newsletter which speaks to becoming an entrepreneur after age 40. Hope you find it useful.

The Three Challenges with Going Into Business Once You’re Older

by Mark Silver

When I look out into the great world of self-employment, many people starting businesses these days are over 40, and some well into their fifties. There are huge advantages to starting a business at that age. Huge.

A few of the advantages include wisdom, experience, self-knowledge, confidence. You might even have a savings account to lean into. Or your children, if you have any, might be old enough to either not need constant attention or to actually help out.

Unfortunately, there are some distinct disadvantages as well.

Many of the disadvantages come from the fact that growing a new business takes time. Some things can happen quickly, but the fact remains that I continue to see it taking the average person two to three years to achieve true momentum and stability. Before that there are all kinds of challenges exacerbated by age.

Challenge One: Decades of Competence

I was speaking with Laura Roeder while interviewing her for The Business Oasis the other day, and she said something that really clicked for me: “In running a business, you are constantly doing things you’ve never done before.”

You know what happens when you do things for the first time? You make mistakes. You’re uncertain. You feel like a fool.

By the time you’ve reached the second half of life, you tend to become accustomed to feeling competent if not masterful with many of the things you do in your life.

If you decide to start a business, you can scratch feeling competent.

Just the other day we were doing strategic planning at a level I’ve never done before. Kate Williams was leading us, and let me tell you, there were many times I felt stooopid. She would say something, and I just didn’t get it. She was making distinctions that took a long time to click for me.

Yet strategic planning has become such a necessity. If I wasn’t willing to feel like an idiot, Heart of Business would miss out on an incredibly necessary part of maturation.

One of the reasons I love spiritual practice so much is that it helps me remain humble and appreciate beginner’s mind in the face of feeling like a fool.

In what ways are you willing to let go of the comfort in competence you’ve built up over decades? Is it okay to feel like an idiot?

Challenge Two: Needing Comfort

When I was in my 20s, I lived in a flat in the Mission district of San Francisco. I paid three hundred bucks a month. My furniture and most of my clothes were second hand or dumpster-dived, except my paramedic uniform which was issued by my employer.

I lived on burritos. I had an okay car and a bicycle.

Now I’m in my forties. We have a house. We eat well (although burritos continue to play a significant nutritional role). We pay for childcare help. There are creature comforts that have somehow inched their way from luxury status to necessity.

Also, my body just needs more support. I don’t recover from all nighters like I did two decades ago. I spend money on an acupuncturist to help me feel vital. It works, but two decades ago the vitality was just *there.*

Because of the time it takes to get a business truly running, it can leave a household with an uncomfortably tight belt.

At these times, spiritual practice becomes deeply nourishing. It helps me distinguish the “shadow comfort” of material items, as my friend Jennifer Louden calls them, from the true nourishment my heart is needing.

For you, what has inched from luxury to the necessity?

Challenge Three: Realistic Expectations

What was that quote? “Do everything now while you’re young and still know everything.” There’s a simple confidence and tackle-the-world oomph that people have when they’re young.

As we age, we experience the full breadth of life. People die. Opportunities don’t come through. Failure happens.

Age may bring groundedness and wisdom, but it also brings more caution. Instead of the automatic, “Hey, let’s go tackle that mountain,” there’s more of a “yes, but…” that tempers our dreams.

Going full out can make us look foolish sometimes (see Challenge One above). Mistakes happen. Things don’t work. Yet, going full out brings the gift of being in motion, of belief.

This is another reason I love spiritual practice. Deep heart guidance is a more than adequate replacement for blind foolish confidence. The challenge, of course, is to not let your “realistic expectations” undermine either your guidance or your confidence.

What guidance, or straight-up blind, foolish confidence, is calling to you? What realistic expectations can you set aside in service of moving your business forward?

These three challenges, decades of competence, needing comfort, and realistic expectations can sink those of us starting businesses who have a few years under our belts. Thankfully there are remedies in the heart for these.

Which of these challenges do you face? Or are there others I haven’t named? And how do you work your way around them?

The best to you and your business,

Mark Silver (at

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