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

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 (note: The Business Oasis ended November 2010) 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?

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30 Responses

  1. Hi Mark

    I grew up in a world where there were no cell phones, no Internet, no mp3 players, and where computers were gigantic machines that inhabited entire rooms – and had way less processing power than today’s smallest laptop.

    So in building a digital-based publishing business I get to feel stoopid on a pretty regular basis…

    What I feel is good about this is that the constant challenge is likely good for offsetting the possibility of falling prey to Alzheimer’s disease!

    love

    Leo

  2. Hi Mark,

    Good points. “Age brings more caution” speaks to me because over the years more and more people tell us we can’t do this and we can’t do that — and we listen to them. What do they know?

    The world’s all invented. Go forth and invent something new and share it with enthusiasm!

    Thx. Giulietta the Muse
    .-= Giulietta Nardone’s lastest post: What the hell

  3. As an artist, I have spent a big part of my life doing things I don’t know how to do. Sometimes I look back on a week and realize about 90% of my activities were taking me to some new edge. It can be exhausting, and I am well acquainted with failure. I’m also temperamentally unemployable, so entrepreneurship is my only desirable option!

    My challenge in my sexy grandma years is energy level. I am liking what you say about acupuncture. Time to look into that.

    And yes, time to dive into something completely new again.

    1. Wow- 90% new in a week- that’s a high level of being on an edge. I personally need more comfort than that- but I’m celebrating you and your sexy grandma years!

  4. Hey Friend! Great post, as always, may I just rave about your ability to write such wonderful on target helpful deeply nourishing things each week? How you do it, how do you do it!

    I was coaching a woman at my Kripalu retreat this past weekend about how she had lost faith and will in her life. There is something very fascinating there, to me, as I have experienced it too… losing our mo-jo after a certain age. Can you write an article about that?
    .-= Jennifer Louden’s lastest post: =-.

    1. Losing our mo-jo after a certain age? Maybe you should write a guest post for us on that. I am in my forties, but only just, and I don’t have personal experience with really losing mojo like that- so although I can give the standard – love-compassion-mercy thing, I’d rather someone who can really speak to it write it.

  5. Thought I was the only one — needing more time to get vitalized, feeling “materialistic” about things that I now think of as necessities…and of course there’s an innate sense of “I should know this stuff by now, heck I’m 45!”

    My spiritual practice is definitely vital to pulling through all the other stuff.

    Thanks again Mark, always a wonderful pleasure reading you!

    Peggie
    .-= Peggie’s lastest post: Finding Love -amp Writing

    1. You are so welcome- and I’m glad you want to support that path. Down below this comment Bonnie McFarland left a comment- you two should connect. She’s doing fantastic work in that arena.

  6. The biggest challenge I have in my business (I’m 46 and have been self-employed since 1989) is the areas where I’ve gotten kicked down a bunch of times and have given up.

    And I definitely see that with the people I coach. As we get older, we just have a larger repository of “proof” that going for what we really want is a waste of time that will never work.

    Lately I’ve been getting a lot of help from the question, “When I’m believing all that ‘proof’ that my dreams will never come true, what kid of Higher Power am I believing in?”

    Put another way: “What kind of Higher Power would put the desire for greatness into me, then make me fated to never get it?”

    That question never fails to show me that I’m NOT turned toward the Highest Good.

    It also makes it practically automatic to turn to the REAL Higher Power…. Which is easily able to overcome all the “proof” I’ve gathered that my business can’t get to the next level, or that whatever I dream for can’t come true.

    So that’s the biggest challenge I see in getting into business at an older age… And also one of the things that’s helped me the most in getting past that challenge.
    .-= Dmitri Bilgere’s lastest post: How to use

    1. I love it, Dmitri- I use something very similar. There’s my beliefs and then there’s God. Hmmm… wonder which one I should listen to?

  7. This is excellent, Mark! Even if you didn’t mention those of us starting businesses at 60. 🙂

    It is challenging for all the reasons already mentioned.

    Starting “Savoring Your Sixties,” doing a blog, using social media for biz, have given me tons of stuff to be learning, which keeps my brain working . That’s good.

    Plus doing something new is energizing and revitalizing, stimulates our creativity, and gets us out of our ruts. All good!

    And it’s still hard to keep at it sometimes!
    .-= Bonnie McFarland’s lastest post: Growing Older May Not Be As Bad As You Think =-.

  8. Great article (as usual) about a large group of folks who are often overlooked in discussions about self-employment.

    There seems to be a general motif here about caution and risk aversion with which I can readily identify. From the standpoint of financial risk, it’s not just about the resources one may bring to the entrepreneurial table. It’s also about the shorter time frame “silverpreneurs” have to recover financially should their self-employment efforts consume a significant portion of their savings. It’s one part of the entrepreneurial calculation that’s clearly age-related.

    Thanks for the typical clear-eyed and soul-filled article!

    1. Hi Craig- really fantastic point. If you wipe out at age 25, you can take ten years to recover and keep going.

      Wipe out at age 65… by the time you recover you may be done.

      Reminds me of a quote from I forget who: “We all die with our to-do lists unfinished.”

      And thank you for your kind words.

  9. Thanks Mark – it’s so nice to be reminded that feeling stoopid isn’t a result of deficiency on my part, it just goes with the territory. I am launching a new business (and defining it) and a blog while celebrating my 50th birthday year, and I am learning learning learning.

    Perhaps a subtitle should be “The Stoopiteers Club”! I’m proud to be a member. 🙂
    .-= Susan T. Blake’s lastest post: Bird Brains -or- How Do Birds and People Learn =-.

  10. I am so happy to see this addressed. Twenty years ago I spent two years writing for the senior population, and now I’m part of that population!

    In my 50s now, I’ve discovered the same things everyone here has mentioned about time and energy.

    At the same time, my work wants to become less about me and more about something larger. The test is: How can I live my values, and have a business that will see me through my senior years, and do all this within the limitations of age? I think this opens up an important conversation.

    1. “The test is: How can I live my values, and have a business that will see me through my senior years, and do all this within the limitations of age?”

      Yes! I think you’ve summed up the challenge quite well. Now on to the conversation…

      – Craig

  11. Mark – Thank you for giving words to the collections of thoughts and feelings trying to rise to the surface of my brain, and for doing so with such grace and kindness that it is safe to identify myself in your writing.

    Although I’ve been self-employed for ten years, now in my mid-50s, I wanted and needed to reinvent myself for the next phase. The need became urgent when the industry in which I have been working for 15 years went comatose last September.

    Reinventing myself for a new – and broader – market takes experimenting, and patience. Plus determination to find the path through not knowing that holds self-compassion.

    I am not there yet, but much closer than ten months ago.

    Thanks again for your words, and all the comments.
    .-= Barbara Breckenfeld’s lastest post: Celebrating imperfection =-.

  12. I saw a quote by actor Will Smith the other day that really speaks to your Challenge #3:

    “Being realistic is the most commonly travelled road to mediocrity.”

    Thanks for summarizing so well some of the challenges that face my clients. To get today’s technology driving their businesses, they have to be sometimes willing to feel “stoopid”, as Leo mentioned; to be attentive to “shadow comforts” versus essential ones; and to go beyond realistic to get in motion to support their unique ways of making a contribution.

    Even with four or five decades of life experience, change isn’t usually comfortable, and being an entrepreneur is choosing a life with constant change built in. Thank you for reminding me that it’s rather wonderful to support a community of such courageous people.
    .-= Karilee’s lastest post: Consistent Marketing Mathematics =-.

  13. Interesting…but as someone who is definitely in the age category you are writing about and starting a business, I have to say that I don’t share those concerns.

    Perhaps it is because of my own individual situation. My husband’s abandonment, loss of all material possessions and becoming sole head of household responsible for three children, may have provided me with a strong basis for launching my business.

    Here’s how: 1) Feeling Stupid: I love to learn, always have. My divorce provided lots of learning opportunities. Never having gone through a divorce, I could have felt stupid, and yet, I didn’t. Not knowing something, is not a big deal. No one knows everything, no matter their age.

    2) Needing comfort: I haven’t been comfortable in nearly a decade. I lost every material possession including our home. I have lived without a car, without a phone, and suffered through various utility cut offs. And yes, I have been hungry. Enough said.

    3) Realistic Expectations: Yes, I have lived long enough to have seen a lot of trouble.

    But age is not the only factor that can contribute to a cynical attitude. I was a television news reporter and producer when I was younger which exposed me to some very sobering situations.

    And still, I refuse to let the downside of life convince me that there is no upside. I believe that amazing things can and do happen every day.

    I hike, kayak, practice yoga and don’t let a chronological age define me. In fact, the only numbers that I am interested in, are those that tell me that my business is in the black!

    1. Karen- That’s fantastic. Sounds like you’ve walked through some really strong situations that have helped you access a deeper wisdom. Beautiful! I’m grateful you are where you are- the more people who can shine like that the better.

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