Are you suited to work for a start-up?
By Ken Pelczarski, Contributing Editor | TLT Career Coach March 2026
It’s crucial to choose a start-up company where the upside potential outweighs the downside.
Working for a start-up can be exceptionally rewarding if the company is successful. It can be a huge disappointment, however, if the company never gets off the ground to achieve any level of success. Choosing a start-up company where the upside potential outweighs the downside is crucial to a satisfying experience.
Let’s look at the definition of a start-up by Wikipedia:
A startup or start-up is a company or project typically undertaken by an entrepreneur to seek, develop and validate a scalable business model. Startups are new businesses that intend to grow large beyond the solo-founder. It is typically characterized by an innovative stance, a potential for rapid growth, external funding and vulnerability.
Going to work for a start-up can turn out to be a pivotal move and bring your career to new heights. You may acquire new learning, more responsibility and a greater level of success than you ever imagined.
Before you decide to accept a position with a start-up, it is important to ask yourself the following three questions:
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Are your personality traits and work style compatible with a start-up?
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Is the timing right and can you reach your career goals with a start-up?
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Are you choosing a start-up that is a good cultural fit and is likely to be successful?
Let’s examine the three questions above in some depth.
1. PERSONALITY TRAITS
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Perseverance. Are you mentally prepared to work through the inevitable setbacks and ups and downs?
Perseverance, resilience and determination are important qualities needed to get you through serious down periods that inevitably occur in the process of building a start-up. Even the most successful start-ups experience numerous failures to fight through along the way.
“If you are going through hell, keep going.”
— Winston Churchill
“The life of a startup is full of ups and downs, an emotional roller coaster ride that you can’t quite imagine if you’ve spent your whole career in a corporation.”
— Harvey Mackay
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Proactive. Are you the type of person who does not hesitate to act when a problem needs to be solved?
Start-ups rely on key employees to utilize their knowledge and experience to make timely decisions to take advantage of opportunities. To some degree, you can “hide” in the corporate world while taking your time to make critical decisions and take appropriate action. In a start-up, your lack of decisiveness and action may cost the company money and will be noticed by your superiors.
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Creative. Do you thrive in an innovative company culture?
Many start-ups are founded on innovation and new ideas. You may fit well into a start-up if you “think-outside-the-box” and excel at solving problems in unconventional ways. A big reason that many start-ups succeed is that they are selling products and/or services that are different from their competition while solving a problem and saving the customer money.
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Versatility. Do you enjoy wearing multiple hats?
You are much more likely to wear multiple hats with a start-up versus a medium-to-large-size company in the corporate world. In a small start-up operation, you may frequently be asked to help in areas outside your main role. If you already possess a broad functional skill set and/or if you want to expand your skill set, you may find it rewarding to work for a start-up.
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Visionary. Is the potential for enormous long-term company growth a motivator for you?
When you work for a start-up, it helps mentally to be a big picture thinker instead of just looking at results today, next month or next year. You may not see your desired level of success in the first year or two. Ambition and passion combined with patience and realism is a valuable quality for a start-up employee.
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Risk-taking. Are you willing to accept a job offer with a start-up when you know that between 60% and 90% of these types of companies fail?
Even when a start-up looks like it will eventually be a success, it will still have a good chance of ending up a failure. You need to be somewhat of a risk-taker at heart to play the odds and commit to work for a promising start-up.
“A pessimist sees the difficulty in every opportunity; an optimist sees the opportunity in every difficulty.”
— Winston Churchill
2. CAREER GOALS AND TIMING
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Short-term career goals. Are your short-term career goals compatible with the average start-up?
Decide for yourself if you have specific short-term goals that a start-up may not be able to satisfy (e.g., managing a certain number of people, working for a company with greater sales volume, settling into a comfortable long-term role). If you do not examine your short-term goals closely before accepting a job offer, you could easily find yourself leaving the start-up within one year.
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Long-term career goals. Do you want to accomplish greater things in your career than most of your peers?
In much of the corporate world, things may change and advance too slowly for your tastes. A start-up may be ideal for you if you have lofty goals that might take three to five years or more to achieve. You may be able to accomplish more than most of your peers in the long run if you are willing to work extremely hard with the right team at the right start-up company.
“Always wake up with a smile knowing that today you are going to have fun accomplishing what others are too afraid to do.”
— Mark Cuban
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Timing and risk level. There are certain times during your career when working for a start-up will fit better than other times regarding your career goals, motivation, family support and ability to take a risk.
a. Is your work record solid in recent years?
You can more easily afford to take a risk when you have not made many job changes in recent years. If the start-up with which you are employed fails in the first year or two, this short-term job should not be seen as a blemish on your resume.
b. Are you between jobs?
Especially if you have always thought about joining a start-up, this may be the ideal time to do so. If you decide to leave the start-up in the short-term, you will have gained new learning and acquired new experience. You will have also stayed employed and productive, which is a plus in the eyes of a prospective employer.
c. Are you able to work long hours?
Most start-ups either require or simply appreciate a key employee working extra hours during the week and on weekends. You need to decide if you have passion for the work with the specific start-up since the demanding work schedule may continue for several years.
d. Do you have family support?
If you are married or have a significant other, you will need to learn if you will have full support from your spouse/partner. Be sure that your spouse is aware of the long hours and the mental strain that will come from the frequent ups and downs. If you have children, you will need to consider their needs and if you will be away from home too often. Ideally, your spouse/partner will have the opportunity to meet the founder and executive team in person to get a better feel for the work environment and demands.
e. Have you worked for a start-up before?
If you have worked for a start-up in the past, you should be able to make an informed decision on whether to accept a job offer with another start-up. In this case, you should be well-equipped to measure the start-up’s likelihood of success and the level of risk you are taking.
“I could either watch it happen or be a part of it.”
— Elon Musk
3. CHOOSING THE RIGHT START-UP
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The founder. Does the founder have a good track record and industry reputation?
Researching the founder is a critical aspect of evaluating the start-up. Look at the successes and failures in the founder’s past. Make sure you have a similar vision to the founder’s vision regarding the company’s future growth and how it will happen. Talk to the founder directly about his/her commitment to succeed. Obtain the opinions of industry contacts about the founder’s ethics, reliability, how he/she conducts business and past successes.
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The executive team. Is there a strong executive team already in place?
Make it a point to meet the executive team to evaluate their talents and see if you could work effectively with them. If the founder is in the process of adding more team members, find out his/her goals and hiring criteria.
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A solid business plan. Is there a strategic plan in writing that lays out realistic goals for ambitious growth?
A start-up’s business plan is typically for three to five years in length. You would rightfully be hesitant to join the company if there is no business plan in place. A business plan should state the start-up’s core business, marketing strategies, customer targets, geographic focus, profit and revenue goals, organizational structure, hiring plans and funding sources.
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Financing. Is there adequate financing, including from outside sources, to support business expenses for the long term?
Outside funding is common for start-ups. You need to learn what current funding commitments are and for what length of time. Reliable funding sources are critical especially for a capital intense business. Find out from the founder if there are contingency funding plans and if you will potentially be asked to invest money. If you are asked to invest, you would be wise to negotiate an equity position in the company.
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Market for the products and/or services. Is there an established market for the company’s products?
A start-up is unlikely to have great success if a.) the market is highly saturated for the company’s products or b.) there is little or no interest established for the company’s newly innovated products and/or services. If you have a lot of experience in the industry, you should have a good feel for whether there is a void in the market for the company’s products. You can also learn more about the market through research, surveys and word-of-mouth networking. Finally, do research into whether there have been mostly successes or failures among other start-ups in this field.
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Length of time in business. Has the start-up already earned significant revenue and built a positive industry reputation?
It is generally more desirable to work for a start-up that has already been in business for a year or two, especially if they have had some success. They would likely have an established organizational structure with proven ways to acquire new business. Learn when the company was founded, current annual sales and any key pieces of business in the sales pipeline. If the company is established for a year or two, you should be able to obtain feedback from industry contacts about the reputation they have built.
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Long-term need for the target position. Will there be a continuing need for the position you are targeting?
Relative security of your job is obviously important. As with any opportunity for which you are interviewing, you will want to learn how the position is expected to change and grow over the next three to five years. Get the founder’s take on what additional duties besides your main role that you may be asked to handle at the beginning. Learn if the position will be more focused in one area over the long haul and then decide if that is how you would like to grow with the company.
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Position authority and freedom. Will you have the freedom to implement your strongest skills to influence company growth?
If you fit the ideal profile of a key start-up employee, you will obviously want to play a big part in accelerating company growth. To be in a position of great influence, you will need to have as much authority and freedom as you can manage. Learn from the founder what restrictions there will be on actions you can take without approval. Find out if you will be able to spend your budget the best way you see fit. You can then decide if you will be following orders too often instead of acting independently.
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Compensation. Will you be earning compensation that is commensurate with your level of responsibility and risk?
Ideally, you will be going to work for a start-up that is financially strong enough to pay key employees better than a comparable job in the corporate world. Higher compensation can come in the form of any combination of base salary, projected salary increases, bonus incentives, profit-sharing, car, equity potential, stock options and various perks. If initial compensation is not at your desired level, you might want to look at whether there is a good chance of exponential growth in compensation in the short term. A multi-year contract is something to try to negotiate for added protection.
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Risk of failure. How likely is the start-up to succeed?
If you are considering going to work for a start-up, it is in your best interests to find a company that has a better chance of succeeding than the average start-up. Depending on the source, 60%-90% of start-ups fail in the first few years. Look at determining factors such as whether a.) multi-year profit projections are realistic, b.) there are long-term business contracts in place with customers, c.) the company is relying on just one or two major customers, d.) the market is responding positively to the company’s products, e.) there is adequate funding, f.) there is a solid business plan and g.) there is a strong executive team in place.
“I knew that if I failed I wouldn’t regret that, but I knew the one thing I might regret is not trying.”
— Jeff Bezos
It is highly recommended that you do your due diligence and learn as much as possible about the start-up company you are considering to be your next employer. In addition, do some serious soul-searching regarding how happy, comfortable and productive you would be in a start-up work environment. Finally, once you determine the likely level of risk, it is a personal choice as to how much risk you are willing to take.
Ken Pelczarski is owner and founder of Pelichem Associates, a Chicago-based search firm established in 1985 and specializing in the lubricants industry. You can reach Ken at (630) 960-1940 or at pelichem@aol.com.