Business Hindsight

Business Hindsight

What You Wish You Would Have Known

Looking back and reflecting over your career, there are probably a few challenges you’ve encountered over the years that you wish you could have been better prepared to face. It’s a feeling shared by almost everyone: how clearly events look in hindsight, once all the facts and outcomes are fully understood. To honor the mutual fumbles that many of us share, we decided to take a closer look at whether or not individuals were prepared to enter their industries during the early days of their profession and the things they wish they would have known in the beginning. Several weeks ago, we distributed a survey to many of our readers, and we’ve compiled some of the best responses here for you to explore.

Among all of our survey respondents, about 60% felt they weren’t prepared for the challenges their respective industries had presented them with during the early years of their career. Just under 40% of respondents felt they were fully prepared. Interestingly, very few of the respondents came from the same industry categories.

  • 38% of the respondents were business owners
  • 52% were employees within companies
  • 10% were self-employed

Several people mentioned that while college and other training did get them ready for some of the basic elements of their careers, there were several factors, curveballs, and industry changes that they weren’t equipped to handle. Some of the more notable responses said:

  • “Education taught me the technical aspects needed for my job. However, knowing how to better understand human behavior would have also been helpful.”
  • “I have been working for thirty years primarily in three industries: aircraft manufacturing, steel forging, and now an electric utility. These are very diverse industries, but all three are union environments. Different unions create different challenges, and there is no one size fits all solution.”
  • “The issues facing our business today are far more complex than when I became involved with the industry. Our clients have become more sophisticated and educated due to the information that is readily available on the internet and data analytics.”
  • “No one could be ready for all the aspects and challenges of being in business. Yet again, that is part of the enjoyment of owning your own business.”

Here’s a look at several of the concepts our respondents wish they would have known before starting their own business, joining their company, or starting their career within their industry:

“Learn the language. Every job, industry, manufacturing facility, airline, construction company, etc., has its own language. Some of it is slang, some of it is technical in nature, and occasionally some if it can be regional. The faster you can start incorporating accurate elements of the language into your everyday conversations with your co-workers, bosses, or more importantly your customers, the more credible you become. It hastens the journey from new guy to insider.”

Mark S.

“The most important thing I have learned that I didn’t know when I started is that “emotion trumps everything.” How you make your customer feel is critical.”

Donna F.

“Some specific areas I wish I’d known more about would be human resources and employee law. I wish I had known how demanding it is, how many hours are required, how exhausting and stressful it can become. I wish I had known that you truly can’t predict the future, and sometimes even the best thought-out plans don’t materialize due to outside forces. You have to have a backup plan and a backup plan to your backup plan. And a reserve. My best decision was surrounding myself with smart, capable, trustworthy people. I can’t possibly know everything, so it’s very important to employ, contract, and befriend people who fill in my weaknesses.”

Erica D.

“I wish I would have started with more education on the types of people I would need to hire, train, and nurture to grow my business. Pre-hire testing has been a great tool the last 10 years.”

Brian M.

“While I was prepared for my entry-level role in the company, I have been there for 27 years and am now the President/CEO of a large not-for-profit (just under 800 employees). I don’t think you can be totally ready for any such role, but I felt that I had the opportunity to prepare myself as much as possible. I must continue to seek learning opportunities to ensure that I am prepared for the challenges ahead.”


“After almost 30 years in business I still have issues with the state and federal tax laws. There are few easy-to-understand publications, and for a small business owner, it’s almost impossible to keep up with the changes. Taxes are burdensome and confusing, and then to have to hire experts just to understand the issues can be even more expensive.”

Gayle V.

“Opportunities will arise that may pull you off course, but you need to know when to stay true to your plan and when to make a conscious detour. It’s also very important to keep good data on contacts and follow up with them.”

Jane L.

“I wish I would have known more about the scope with which legal issues and government agencies play a part in addressing and resolving employment, benefits, and labor issues.”


“I think it is good to know up front the value in networking. You may not need the contact immediately but it may be helpful as you develop. Also, knowing that most relationships and business transactions take time to cultivate. You must be patient as the relationship develops.”