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There’s No Perfect Time to Be Entrepreneurial

This guest post is by Mr. Broke Professional: the husband in the husband/wife team behind

When you tell friends or family that you want to start your own business, you will likely hear one of two responses.

  • Response A: “You can’t do that!  You’re too young!  You need to keep working for your employer for a few more years.  That way you can develop the skills and contacts you will need when you start your own business.
  • Response B: “You can’t do that!  You’re too old!  You have kids and a big mortgage and private school educations to pay for.  Just be thankful in this economy that you have a decent paying job.  Once you save some more money maybe you can consider branching out (maybe).

No Perfect Time to Start a Business

Like choosing when to get married or when to start a family, there is no perfect time to branch out on your own.  There is no perfect time to start an entrepreneurial adventure.  Yet, at the same time, the opportunity is always out there for anyone willing to risk it.  There is no guarantee of success if you do.  but at the same time, if you stay employed by somebody else you are always just two short words away from your whole world being turned upside down.

I am a young professional and my goal has always been to go off on my own.  The problem for me and most people in my situation is one of a lack of knowledge and contacts.  Another problem is that in certain fields (mine being one of them), clients do not enjoy the fact that I look so young.  The issue that arises as you age is one of “golden handcuffs.”  You are earning too much and lifestyle creep has set in to stay.  You can’t afford a way out.

Like many people in their late twenties (or early thirties), I probably do lack the skills and contacts to have a successful business as soon as I branch out on my own.  At the same time, in most instances when you are younger you do not have anything really holding you back.

I have read book after book about business.  When I work at my job I keep note of how they run their business as much as how they practice their profession.  I go to every seminar I can on the subject of business development.  The problem is, you will never know if you can make it in business unless you try it for real.  You can not simulate running your own business.

Trying to Find Some Support

My wife’s father started what is now a very successful business in his late twenties.  At the time he had a wife and two children.  I spoke with him about my dreams one night and even he told me to bide my time and wait. The conversation went as expected, when I started with

There’s no perfect time to start a business though

You should take more time to learn your trade…I don’t want you guys to have to struggle through those early years like we did.

To be sure I understood what he is saying, just like I understand that most businesses fail.  At the same time, you will never know if your business can succeed or not if you never take the risk and start one.

Now I recognize that there are moments that are better than others for starting a business.  Moments where opportunity and luck meet in the perfect middle ground, and you just know that starting your own business is the right play.  You may have an opportunity to buy out the company you work for.  Or a big client may tell you that they will jump aboard your new business if you go off on your own.

For most of us, however, we are stuck with a sense of vague uncertainty, and the fear of constantly waiting for that “perfect moment,” but never actually following through on our passions and dreams of starting our own business.

I do not believe that I have the right to follow my dreams at all costs.  I am married and I have another person to consider.  Nor do I believe that my own business is a manifest destiny or something that I am entitled to.  But at the same time I do know that there’s no perfect time to start my own business, and that is at heart what I really want to do with my life.

To summarize, I guess the question for me is: So how is right now any more imperfect a time than any other?

Any thoughts on people going through such a crises of conscious?   Any resolutions?  I am looking forward to reading and responding to your comments.

Broke Professionals is a personal finance blog aimed at overeducated and underpaid.  Join the husband/wife blogging team of Broke Professionals as they attempt to dig themselves out of a combined six figures in student loan debt.



  1. I agree that when most ppl say right now is not the time, their real reason is a sense of fear and uncertainty. But at the same time there are bad times to start a business. one is when your life is already in flux and already has a lot of uncertainty. Adding another element to it (a business) will make you even more stressful. During these times, it’s best to take it easy and wait for a better time.

  2. Henway,

    That is really true. There are certainly times not to do so. For me the fear is my six figure student loan debt. At the same time Mrs. BP (knock on wood) has a good job. We got a 15 year mortgage on the house we’re buying and we’re on target to pay off our student loans in 10 years, so maybe the goal is to wait until we are debt free (and by that point I should be really knowledgeable in my profession) and start the business in my early 40’s. That seems to make the most sense, but when you have that drive and desire to have something all your own it is tough to be that patient.

  3. Market forces should be a factor. But, not any more of a factor than ‘internal forces’. I’m a proponent of swinging for the fences, early and often. Most batters probably give up before even getting up to the plate to face Yankees star Mariano Rivera. But, there are others who will strike out 9 times in a row and go right back up to the plate with the expectation of getting a hit and winning the game. Some have done it. Which are you? Sorry for the length. Thanks.

    • Sometimes you have to *pretend* to have the self confidence to pull it off. If others see that you believe in yourself, (even if you are just *pretending*) they will see you as a success, and cheer you on. You benefit from the positive nudges from others, and will believe more in what you are doing.

      I guess what it boils down to, is don’t show fear or doubt. People pick up on that and will doubt you too.

  4. I’ve been wanting to be an entrepreneur for the longest time. With blogging, I’m working on it. So fun, and such a potentially big business if one can stick it out long enough!

    Cheers, Sa

  5. So many people make excuses why not to start a business, waiting the perfect moment to happens. Well, as you say, there is no perfect moment.
    Age doesn’t matter. If you want to be entrepreneur, you have to start right away.

  6. My husband started his own business when I was pregnant with our first and we had 200k of law school loans and credit card debt. It worked out well for us.

    My advice would be to do it long before your kids reach about second or third grade, the sooner you start the better. At some point, you’ll need to be spending money on your kids – $100 registration fees for sports leagues, $40 dollar cleats, gas money if they make the travel team, etc. Eventually, kids are no longer happy playing with cardboard boxes and they (or their peers) will notice if their clothes are cheap and/or poorly fitted.

    I look back on those early years – we paid our bills in the following order – health insurance, house, utilities, car insurance, visa, and then student loans. Sometimes student loans didn’t get paid. I think it would’ve been a lot more stressful if we’d have had 12 year olds coming home from school saying they needed 15 bucks TOMORROW for a new calculator at the same time the SLSC was leaving messages on the machine.

  7. @Lisa – I think you are write about the “fake it until you make it” mentality, to some extent image talks. Of course, money talks louder.

    @Yakezie – I agree, I truly believe only certain people have the goal/drive of being entrepreneurial. If you have it, then sometimes it is a hard mentality to satisfy.

    @Ben – I agree with you, but as I said in the post, who wants some kid right out of law school (pretty much) as their lawyer? I hope I have what it takes to avoid malpractice, obtain clients, satisfy clients, etc., but sometimes it is so much easier to “keep learning” and take the paycheck….as much as that is not my ultimate goal. Very tough. The house is going to make things more difficult in terms of walking away.

    @Philly area- I am in Abington, Pennsylvania right now…so I am back in the Philly area where I grew up. That is crazy and awesome that you guys were able to pull that off and come out the other side. I am sure you do not regret a single thing now. Having the self-confidence to do it is really awesome. You give me some hope and faith in my own dreams.

  8. You are right, there is no perfect time. I went through this question at age 38. Discuss it with your wife objectively, bring out the downside, the difficulties and approach it conservatively. Can you start it before you leave your regular job? Make sure you have all the insurance in place and other foundational items at the beginning of this. Have an agreement with your wife about milestones and goals and what you will do if you do not meet them. It is important to talk everything out before you start.

  9. I am a lawyer so any talk of wanting to start my own business equals a fear of stealing clients (and likely an immediate dismissal). That is the tough part.

  10. I would say, have a plan and prepare as much as you can before taking the plunge.

    The more preparation you make ahead of time, the less chances of you making mistakes. Have plan B, plan C and plan D!

    If you can pull it off keeping you current job, that’s even better!

  11. Would you rather wait and hear the “You can’t do that! You’re too old!” response?

    Are you willing to live with the consequences of failure? Is your spouse?

    Have you considered starting with an older partner (one who has that experience, those contacts and that gray hair and wrinkled brow)?

    Could the needs behind your desire to be on your own be satisfied any other way?

    Children not only require lots of money, they also require lots of time and attention. Trying to devote time and energy to a start up during your children’s formative years can be difficult.

    “Life is like a box of chocolates, you never know what you are going to get.”

    Good luck.

  12. There is no perfect time to start a business, but in a way I feel that a recession is a great time. It throws up certain opportunities and makes you have to learn to be adaptable.


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